Dating Should Be about Pursuing Joy with Tracee Ellis Ross

Actress, director, producer and businesswoman Tracee Ellis Ross joins IMO to answer a listener question from a man who has been unlucky in love but wants a partner and family. Tracee discusses how she learned to embrace being single for much of her adult life, why she feels ready to date again, and shares her dating checklist. Plus, Craig offers his thoughts on what men are looking for in their dating lives. Have a question you want answered? Write to us at imopod.com http://imopod.com. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Michelle Obama?

  You know, it's, it's sort of innocently sweet and it's not so hard over the head. Like, can you stand alone in a room?

• 0:06Speaker 01

  That's why I like the question, because I would ask that all wrong.

• 0:08Michelle Obama?

  Right, that's just the thing.

• 0:10Speaker 01

  I would ask that same question.

• 0:12Michelle Obama?

  Are you an insecure trifling ass?

• 0:13Speaker 01

  That is exactly right.

• 0:14Michelle Obama?

  Are you so insecure?

• 0:16Speaker 01

  Yeah.

• 0:16Michelle Obama?

  That you can't handle a strong woman?

• 0:19Speaker 01

  Are you uncomfortable with my bigness?

• 0:20Michelle Obama?

  You know, and then...

• 0:20Speaker 01

  I would ask it all wrong. He would be squashed from the start.

• 0:24Craig Robinson?

  Because I am a boss. I am a boss.

• 0:26Speaker 01

  I'm a boss. Are you okay being the fella?

• 0:28Michelle Obama?

  Can you level up? Can you level up? And then he's running away going, I don't...

• 0:33Speaker 01

  She's aggressive.

• 0:47Craig Robinson?

  How you doing?

• 0:48Michelle Obama?

  I'm doing great. Yeah, feeling good. Another day, alive.

• 0:55Michelle Obama?

  We're getting to that age where, you know...

• 0:57Craig Robinson?

  No, we're not.

• 0:57Michelle Obama?

  I'm just, just blessed and woken up, got up. You don't think we're at that age? You're older than me.

• 1:04Craig Robinson?

  No, I, I, yes.

• 1:06Michelle Obama?

  Well, we are.

• 1:06Craig Robinson?

  Yeah, but I...

• 1:07Michelle Obama?

  We were in our 60s, my friend.

• 1:08Craig Robinson?

  I know, but I, I'm hoping I got a good 20 more left. That's what I'm shooting for, at least.

• 1:14Michelle Obama?

  But, you know, we're at the age now where, you know, it's not so tragic.

• 1:18Craig Robinson?

  I know. Well, did you get enough rest last night, old lady?

• 1:21Michelle Obama?

  I did, I did. I, you know, the girls came over for dinner and I was so tired that I left them at the table, which is unusual, because I love hanging out with my girls, but I was that sleepy. I was like, you know what? Mom's going to bed. You can sit here and talk to your dad. So, so, but yeah, I, I got to bed early and had plenty of sleep. How's your Airbnb feeling?

• 1:44Craig Robinson?

  Oh, my gosh.

• 1:45Michelle Obama?

  Still happy with your situation?

• 1:47Craig Robinson?

  So, I'm so happy that I did not go to dinner last night. I left here.

• 1:51Michelle Obama?

  Just to stay in your Airbnb house?

• 1:53Craig Robinson?

  Just to be able to chill in my Airbnb in West Hollywood. And guess who visited me this morning to do their laundry?

• 2:01Michelle Obama?

  Who?

• 2:01Craig Robinson?

  Leslie. You know, my daughter's in town here and she came over to bring her laundry to do. I mean, that's, that's why I like...

• 2:08Michelle Obama?

  Why does she have laundry? Is, how long has she been here?

• 2:10Craig Robinson?

  You know why? Because she works out every day.

• 2:11Michelle Obama?

  Oh, okay.

• 2:12Craig Robinson?

  So, she had a whole bag full of gym clothes and underwear and stuff and just put it in. And I was like, yeah, come on over. And then we had breakfast and... And then she went to meetings.

• 2:22Michelle Obama?

  Yeah.

• 2:23Craig Robinson?

  And I think she's gonna come stay with me tonight, so.

• 2:25Michelle Obama?

  I'm learning a lot about the Airbnb life since we don't do that.

• 2:29Craig Robinson?

  You don't get to do it.

• 2:30Michelle Obama?

  But the girls do. Malia and Sasha, whenever they're traveling.

• 2:34Craig Robinson?

  And so our kids, Avery and Leslie and Emily and Elena, they all, they have no qualms about, let's go, let's find a place.

• 2:42Michelle Obama?

  It's really a different intergenerational use. I mean, young people, they like being in a home. Well, a lot of times when they're traveling, they're sharing with their friends, they're dividing up a house and, you know, so.

• 2:55Craig Robinson?

  And I find I've gotten to like it now, so, you know, I was a strictly hotel guy.

• 3:01Michelle Obama?

  Yeah.

• 3:02Craig Robinson?

  I wanted maid service every day. I wanted to be able to go down to the bar or not have to drive anywhere. I wanted, I wanted all that stuff, but then the amenities of having your own place.

• 3:14Michelle Obama?

  Yeah.

• 3:14Craig Robinson?

  That's like a house and you can sort of live the way you normally live is much more appealing.

• 3:19Michelle Obama?

  Well, it sounds like it'd be a good girls' trip, a friend gathering session or, you know, it's a little, little. But anyway.

• 3:28Craig Robinson?

  It's a good.

• 3:28Michelle Obama?

  Well, I'm glad you are comfortable in your Airbnb, mister. So you'll never stay with me ever again, I guess.

• 3:35Craig Robinson?

  No, that's, it's, it's, it's, I would not do that.

• 3:37Michelle Obama?

  Have we been displaced?

• 3:38Craig Robinson?

  You have not been displaced.

• 3:40Michelle Obama?

  Oh, good.

• 3:41Craig Robinson?

  You have not been displaced. It's, you know, but you might want to come visit me every now and then now.

• 3:47Michelle Obama?

  Would you, would I mess up your mojo if I showed up with my motorcade in your, your house?

• 3:52Craig Robinson?

  Well.

• 3:52Michelle Obama?

  Driving up the driveway with.

• 3:54Craig Robinson?

  It, it wouldn't mess up my mojo.

• 3:56Michelle Obama?

  Uh huh.

• 3:56Craig Robinson?

  Might mess up the owner's mojo.

• 3:59Michelle Obama?

  Uh.

• 4:00Craig Robinson?

  It might not mess up.

• 4:01Michelle Obama?

  Well, maybe, maybe I'll stop by and see all your, your mini pools in your house.

• 4:05Craig Robinson?

  Yes, yes.

• 4:06Michelle Obama?

  Well, what are we talking about today?

• 4:08Craig Robinson?

  So we're talking about dating today.

• 4:12Craig Robinson?

  And.

• 4:14Michelle Obama?

  I love talking about dating. Cause I haven't done it in decades.

• 4:18Craig Robinson?

  And, and you know, when we were preparing for this, I was asked the question, when we were younger, did we talk about dating? And I have to say, we, I don't remember talking about dating much at all when we were younger.

• 4:34Michelle Obama?

  I felt like I was way more in your business and I kept my business to myself.

• 4:40Craig Robinson?

  Yeah, but I didn't have much business. I mean, just think about it. I had to be fixed up on my junior prom. I mean, I didn't have any, I didn't, I don't remember having real girlfriends.

• 4:51Michelle Obama?

  Oh, that's the problem with.

• 4:53Craig Robinson?

  College, so.

• 4:54Michelle Obama?

  With, with you and these sports, it's like.

• 4:57Craig Robinson?

  Yeah.

• 4:57Michelle Obama?

  Yeah, spending too much time in the gym.

• 4:59Craig Robinson?

  Yeah, yeah, it really was too much time in the gym and focused on my schoolwork. And then I just wasn't.

• 5:10Michelle Obama?

  But it was.

• 5:10Craig Robinson?

  Dating type.

• 5:11Michelle Obama?

  But it's interesting because, all right, so this is the, the benefits of being the sister of a, of a guy who plays sports, which is one of the reasons why I enjoyed going to your games is like, most of the guys I dated were on the JV team. So me and my friends, we'd show up at the game. So I don't know why you couldn't find a date because I think my first several boyfriends were your teammates or they were younger on the JV team.

• 5:39Craig Robinson?

  They were younger versions of.

• 5:41Michelle Obama?

  Because that was always an important test was, well, what do you think about them as a teammate? You know, are they, first of all, are they good at basketball? So I generally only dated the people that you said were actually good.

• 5:53Craig Robinson?

  Right.

• 5:53Michelle Obama?

  You know, also you and you had this theory about, you know, knowing a person by their on the court behavior.

• 6:02Craig Robinson?

  Yeah, I can't take full credit for that because I really got it from dad. And what, what dad would, my, what my dad would say is you can really tell a person's character by how they play pickup basketball. And the reason is. You can see how hard a person works. You can see if they're the type of person who talks trash. And I've told this story many times about when you first started dating Barack. So Meeh starts to date Barack and we don't know who this guy is. We just like Barack, who's got a name like Barack? And I was, and I'm thinking to myself, it's gonna last about a month like most of your relationships did.

• 6:40Michelle Obama?

  That's not true.

• 6:41Craig Robinson?

  And.

• 6:42Michelle Obama?

  I've had many a long-term boyfriend.

• 6:44Craig Robinson?

  I wouldn't call those guys boyfriends.

• 6:46Michelle Obama?

  Oh, my gosh. See, see what I had to go through. You didn't even call, you didn't even wanna call my boyfriends boyfriends. None of those guys, but anyway.

• 6:54Craig Robinson?

  Anyway, so Meeh pulls up to the house and we're sitting on the front porch, waiting for her to bring Barack. And she gets out of the car and I remember mom's first thing was, ooh, at least he's tall. That was her first thing she said because Meeh was usually posting up her other boyfriends. She said, at least he's tall. And I, and I said to myself, well, it's too bad it's not gonna last. But the best part of it was after we met him and, and she had been dating him for a little while. She said, would you mind Craig taking him to play? And at first I said, no way. I am not doing your dirty work for you.

• 7:34Craig Robinson?

  If, if he turns out to be a bad dude, I am not gonna be the one to say. And you said, come on, please. And I, and I finally acquiesced. And so we went and obviously we had a great time playing and.

• 7:51Michelle Obama?

  What did you learn about?

• 7:52Craig Robinson?

  This is what I learned. Aside from the fact that he is tremendously left-handed, so he couldn't go right at all.

• 8:02Craig Robinson?

  Most importantly, he was a team player, right? Like he fit in with the people. And so I was able to report back to you, everything was fine and, and the rest is history. So anyway, we got off the subject. So, but, and you know, another one of the reasons why I didn't date. Was I went to an all-boys high school. So it, it's not like girls are walking down the hallway and you see one like, ooh, wanna go to movies or something? It was like. Crickets.

• 8:33Michelle Obama?

  Yeah, but you, you know, you're just an all around nice guy. You were, you weren't shy, but you definitely weren't, you didn't, you didn't have some lines. And I think that that's what we wound up talking about. It's like, you gotta, you know, you gotta get your game on.

• 8:50Craig Robinson?

  Yeah, you did say that.

• 8:51Michelle Obama?

  So, you know, I think the politeness of you, you had to wait to hear that somebody had a crush on you or was interested in you. I think you never assumed that.

• 9:03Craig Robinson?

  Right, no, I, you would have had to hit me over the head with the fact that somebody was interested for me to have the nerve to ask them on a date.

• 9:12Michelle Obama?

  Yeah, and for your friends at this stage in life, you know, forget high school, college, because, you know, you're just doing what you're doing then.

• 9:22Craig Robinson?

  Yeah.

• 9:22Michelle Obama?

  How do, how do you think your friends think about selecting, dating?

• 9:28Craig Robinson?

  Here, here's what I will say, and I am dying to get our guest out here because she's gonna be able to help referee.

• 9:36Michelle Obama?

  For sure.

• 9:37Craig Robinson?

  This between you and me, but I will tell you.

• 9:40Michelle Obama?

  I don't know if it'll just be between you and me.

• 9:45Craig Robinson?

  I, I think guys in my generation, when they were dating, they ended up marrying the women they were dating when they were ready to get married.

• 9:56Michelle Obama?

  Yeah, it's like musical chairs.

• 9:58Craig Robinson?

  Exactly.

• 9:59Michelle Obama?

  Just like, okay, the music stopped, I'm sitting on your lap, I love you.

• 10:03Craig Robinson?

  But what I will tell you is, we all ended up getting divorced. And once we started dating again, much more discerning. When I met Kelly, I was not interested in a relationship, not even dating. We just happened to be talking to somebody at the same time. So I'm making a long story short, but the point is, once we started dating, we said, I said, let's figure out if this is gonna work or not work. So we said, listen, let's go somewhere where we can figure out if this is gonna work. So we went to San Diego, the place we always go to. Nice, big house, it was like, you have your own bedroom, I have my own bedroom.

• 10:48Craig Robinson?

  If this doesn't work, we just say, c'est la vie and have a nice weekend. I said, bring your list of things you want to talk about. And I brought my list and my list does 30 different things.

• 11:03Michelle Obama?

  Thirty?

• 11:03Craig Robinson?

  Thirty-two, thirty-two things that I had individually that I wanted discussed.

• 11:07Michelle Obama?

  Thirty-two items?

• 11:07Craig Robinson?

  Thirty-two items. She had three. I was like, this ain't gonna work.

• 11:13Michelle Obama?

  Oh.

• 11:14Craig Robinson?

  But after we went through my 32, you know what she said?

• 11:17Michelle Obama?

  What?

• 11:18Craig Robinson?

  All of yours fit into at least my three categories. I thought I was just doing categories. I wasn't doing the things.

• 11:25Michelle Obama?

  I think that would have been a reasonable thing to think.

• 11:27Craig Robinson?

  I was, I was, I was burned.

• 11:29Michelle Obama?

  You, you go from like, I didn't ask any questions. I was just ready to get married to a list of 105 steps before. But that, that, well, it worked.

• 11:38Craig Robinson?

  It worked because now, I, I mean, you know, everything. I knew everything. She knew everything about me and so it worked out. Thank goodness. But let, let's bring out our.

• 11:49Michelle Obama?

  Yeah, it's time.

• 11:50Craig Robinson?

  Yes, and I, I almost feel like I don't even want to do a formal introduction because this is one of the first times we've had on this show where the guest feels more like a family member.

• 12:02Michelle Obama?

  She just, she really, she got manners.

• 12:05Craig Robinson?

  Sweet, she's got manners.

• 12:07Michelle Obama?

  She was raised right.

• 12:08Craig Robinson?

  Talking about being fun.

• 12:09Michelle Obama?

  No, exactly.

• 12:11Craig Robinson?

  But she's an award-winning actress. She's a screenwriter, a director, an entrepreneur that I want, I want to, I want to hear about this.

• 12:18Michelle Obama?

  You don't, you don't know about pattern? I guess not, you're bold. Okay, I'm sorry, I forgot.

• 12:23Craig Robinson?

  Oh, man. You let me do my job here.

• 12:25Michelle Obama?

  I'm sorry, I'm sorry, I interrupted.

• 12:27Craig Robinson?

  And, and so, uh, without any further ado, Tracee Ellis Ross.

• 12:33Michelle Obama?

  Tracee!

• 12:36Speaker 03

  How are you? I'm so good. Like I said, family. I do, I do feel like family.

• 12:41Craig Robinson?

  We got family in the house.

• 12:46Speaker 03

  Really interesting conversation.

• 12:48Craig Robinson?

  Oh.

• 12:49Speaker 03

  I took some notes.

• 12:50Craig Robinson?

  Oh.

• 12:50Speaker 03

  I took notes in my head and I actually wrote them down out there because you said there's a lot you can learn about how, who a guy is or who a person is by how they are on the court.

• 13:01Craig Robinson?

  Yes.

• 13:01Michelle Obama?

  They let their guard down.

• 13:02Craig Robinson?

  They let their guard down and their character comes out.

• 13:05Speaker 03

  Think I could have used that information. I think, I think I'm, I'm a little late on adding that to my list of how to figure out if he's a match. They're still noted now. There's still time because I'm still single, so noted now.

• 13:19Michelle Obama?

  You know, there's, there's still time.

• 13:21Craig Robinson?

  Guy out there breaking his hip trying to play basketball.

• 13:23Michelle Obama?

  Yeah, I know. It's gotta be a different measure now.

• 13:25Craig Robinson?

  I know.

• 13:26Michelle Obama?

  You know, I made Barack put his basketball shoes up once he got his lip busted when he was in the White House.

• 13:32Speaker 03

  Oh, my goodness.

• 13:33Michelle Obama?

  Playing a pickup game. Yeah, and I don't think many people realize this because he was definitely in shape, athletic. And I remember because you were at that pickup game.

• 13:41Craig Robinson?

  Yes.

• 13:41Michelle Obama?

  And I'm in the White House, actually in the doctor's office, getting an exam. So they're, they're playing at one of the admin gyms and we get the call. We hear that the agents are like, you know, um, Renegades coming back. There's been an accident, you know? And I'm like, ugh, because I'm always like, be careful playing basketball. You shouldn't be playing now. You now have a, a real important job.

• 14:06Speaker 03

  Yeah, people are depending on you.

• 14:07Michelle Obama?

  You know, and, and literally he's coming in with a, you know, a gauze thing on his, on his lip.

• 14:14Speaker 03

  Oh, my God. He didn't need stitches or anything.

• 14:15Michelle Obama?

  He needed like 30 something stitches.

• 14:18Speaker 03

  Oh, my God.

• 14:20Michelle Obama?

  I mean, his, his lip was, I saw it. It was like he took the thing away and I was like, ugh, your lip. And he had some major speech. This was probably Saturday. He had some major speech on Monday and I was like, this is what I'm saying? You know, you're playing like you're tin and now your lip is split.

• 14:35Speaker 03

  That is.

• 14:36Michelle Obama?

  So we, we digress.

• 14:37Craig Robinson?

  Yes, that's okay.

• 14:38Michelle Obama?

  Because no, no, no longer can we, are we dating people?

• 14:42Speaker 03

  No, but I am.

• 14:43Michelle Obama?

  Yeah, I was about to say, I was like, Tracy, Tracy's, you know, my girl.

• 14:47Speaker 03

  Yeah.

• 14:47Michelle Obama?

  I mean, the tale's from the road.

• 14:49Speaker 03

  And I do bring, I bring stories home.

• 14:51Michelle Obama?

  She's got stories. I'm like, what, what's happened? The last several months.

• 14:56Speaker 03

  And it's always eventful.

• 14:57Michelle Obama?

  It's always good.

• 14:58Speaker 03

  Well, the thing is, I stay open. I'm probably more open. Oh, my God, that sounded so wrong.

• 15:04Michelle Obama?

  I didn't mean that, Mom.

• 15:06Speaker 03

  My heart.

• 15:07Michelle Obama?

  Your family.

• 15:07Speaker 03

  My heart stays open.

• 15:09Michelle Obama?

  Your heart literally stays open.

• 15:11Speaker 03

  Yes, yeah, that was hard. More open than it than it should be, but I do date. And it's a fascinating adventure out there, you know. Mostly, though, I think there's really good men out there. I think to a certain extent, I'm a very unique sort of unicorn of a woman. And so it's gonna take a unique person. And in the meantime, I have really learned how to live my life and enjoy it and not sit around waiting. I come, you know, I was saying to someone recently that I'm one of the first generations of choice. And it's not anymore, which really, there was a window and that has shifted. And I do think that that's gonna change dating for women so much.

• 15:56Michelle Obama?

  When you mean you've been the sort of the product of choice?

• 15:59Speaker 03

  Yeah, like the assumption of Roe v. Wade. And the ability for a woman to find her own delight and pleasure and choice around how she navigates dating or how one would navigate dating. And we're in a different world now. And I'm curious what that will look like. It frightens me for younger girls because of many reasons, obviously. But even with the systemic protection of Roe v. Wade, I still was coming up against the cultural norms of being a choiceful woman and owning my own body and my own choices and what it is that I'm looking for in a relationship

• 16:41Speaker 03

  and the ability to negotiate in a relationship, what it is you want the relationship to be between the two of you, as opposed to what society says it should be.

• 16:50Michelle Obama?

  Well, I don't.

• 16:50Speaker 03

  And that's different.

• 16:51Michelle Obama?

  I don't know that we're gonna lose that. I think women, we're used to having a say in our lives. And I don't know whether this. The whole movement is about sort of re-harnessing us. You know, whether is it really about,

• 17:08Speaker 03

  And can that really work?

• 17:09Michelle Obama?

  Reproductive rights, can that really work now that women are educated? And, and, and we're being raised differently. I mean, the truth is, is that men, fathers are modernized.

• 17:21Speaker 03

  Yes.

• 17:22Michelle Obama?

  Right? I mean,

• 17:22Speaker 03

  Mostly.

• 17:23Michelle Obama?

  Mostly they are, you know? And if you were to ask the average man, how are you raising your daughter? Because you love her. The average father that loves their daughter wants them to be excellent, you know? And they want them to have opportunity and freedom.

• 17:39Speaker 03

  And freedom.

• 17:40Michelle Obama?

  When you think about who, you don't want your daughter saddle marrying some guy that chose her because he just didn't think about anything else and was ready at the time.

• 17:50Speaker 03

  Is his choice.

• 17:51Michelle Obama?

  Exactly. So I, I don't think a lot of leaders are thinking about that.

• 17:56Speaker 03

  Yeah, well, and they, they haven't been asked to because I think it's, it's not always a context that if it's an area that you don't have to think into.

• 18:05Michelle Obama?

  Right.

• 18:05Speaker 03

  But I think there is, it is a genuine, regular thought process for me. It's one of the reasons, I mean, we've talked about this, that often I date younger men. And a lot of it is because.

• 18:15Michelle Obama?

  Let's stop on that, folks.

• 18:17Speaker 03

  Oh, my God, we had a great dinner.

• 18:19Michelle Obama?

  On that one.

• 18:20Speaker 03

  We had a great dinner, by the way, where across the table, your husband goes, but why? And I said, well, maybe because I can.

• 18:27Michelle Obama?

  Yes.

• 18:30Michelle Obama?

  This is why I'm saying Tales from Tracy's.

• 18:34Speaker 03

  It's fun.

• 18:34Michelle Obama?

  It's really fun to share.

• 18:35Speaker 03

  Tracy Tale.

• 18:36Michelle Obama?

  But, but, I'm sorry.

• 18:38Speaker 03

  But the, one of the reasons, though, that, because I had to ask myself that question. I was like, what is this about?

• 18:42Michelle Obama?

  Yeah.

• 18:43Speaker 03

  Because I want a partner and so often, and it's not just that I'm older. I'm also very embodied. I am a full, very whole person who knows myself, who is in charge of my life and who lives a very full, just robust life. So. It's not just age, it's like life experience and sort of a difference. But I had to ask myself the question, why? Why does this keep sort of coming up other than they're hot and gorgeous?

• 19:09Michelle Obama?

  There's that.

• 19:10Speaker 03

  There's that. But a lot of men my age are steeped in a toxic masculinity and have been raised in a culture where there is a particular way that a relationship looks. And anything that starts to smell of that for me, I am, I did enough of it where I was controlled and felt like I was a possession or I, whatever those things were, or prize, or, and I just, I have no interest in it and I will not do it again.

• 19:39Michelle Obama?

  I'm sorry.

• 19:40Craig Robinson?

  No, I was gonna say, so it's a generational thing? So it didn't matter how you met them or is it just kind of the guys you're meeting?

• 19:47Speaker 03

  That's obviously, it's a generalization. But, um, cause I have dated men my age, there is a difference. There is an openness that occurs with a younger man around whether it's gender fluidity or not even having an issue with homosexuality. I mean, something as basic as that, that there's times.

• 20:06Craig Robinson?

  I hear you.

• 20:07Speaker 03

  Or I'll be, you know, sitting across the table from somebody and just like, what did you just say?

• 20:11Michelle Obama?

  What century are you?

• 20:13Speaker 03

  Like, oh my god.

• 20:14Michelle Obama?

  Where's your horse and buggy?

• 20:15Speaker 03

  Yeah, like, I'm so sorry.

• 20:16Michelle Obama?

  And your, your bedpan.

• 20:18Speaker 03

  Yeah, for real.

• 20:19Craig Robinson?

  Chamber pot.

• 20:20Speaker 03

  Yeah, you're a chamber pot, you're a chamber pot. Like where I'm just like, yeah, this is not a match. And I don't, I have long been past the age where I feel like it's my job to teach somebody or grow them up, that I'm not interested in. So, um, but it's interesting. I mean, there's so many different philosophies on dating and I have come up with mine. I have come up with what works for me and what makes sense for me and what feels safe for me.

• 20:45Michelle Obama?

  Yep.

• 20:45Speaker 03

  You know? I mean, like, I'm not on dating apps. I have friends that have great success with dating apps, but that's just not something I'm comfortable with.

• 20:51Craig Robinson?

  So you're meeting folks in the wild then?

• 20:53Speaker 03

  That's the only way for me, or someone sets me up, or I meet them at an event, I meet someone. It's usually people that also have a, a level of recognition that. They, you know, have as much to lose as me to a certain extent. I don't know. I mean, I haven't had great luck lately, but I do have to say I'm, I'm moving up on what it is that I'm looking for as a match.

• 21:15Michelle Obama?

  Yeah.

• 21:15Speaker 03

  Yeah. I've had some doozies.

• 21:17Michelle Obama?

  Yeah.

• 21:17Speaker 03

  Yeah.

• 21:18Michelle Obama?

  Yeah. But it's just, I just love watching your life because you were modeling so many things. The next phase, how, how many versions of ourselves we can become at all ages in life. You know, and how to build the life you want. Yes. Not the life that somebody told you, you were supposed to have. And let me tell you, I have, I told you this about the girls and Tracy, just like, you know, she mentors the girls. She's always there for them. But trying to get, trying to make sure that I am not subconsciously sending them these messages about what their life should look like, even like when you ask, are you dating anyone? I mean, that's something that we ask young people in their twenties, you know?

• 22:03Michelle Obama?

  The whole thing about weddings, you know? We talk a lot about that. Yeah. It's just like the pre-proposal and the bachelorette and the pre-honeymoon. And then the three wedding dresses and the, and, you know, have you thought about? The amount of money. Your 32 list items of who you want to marry? Or are you more busy planning, picking out your photographer?

• 22:26Speaker 03

  Yeah, it's interesting, that whole, I, I hope that that is starting to dissipate culturally. I really do. I think it, social media is perpetuating some of those things in a really big way. But I, you know, I did dream of my wedding growing up. And that's not to say that I didn't dream of the bigness of my life. But I could have spent a lot more time dreaming of my life. And, and you know, as much as grief does surface for me around not having children and not having a partner, I still wouldn't want the wrong partner. That's a great point for people out here. I, I, I don't, I'm not interested in that. You have to make my life better. It can't just be, you know, I'm in a relationship to be in a relationship.

• 23:11Speaker 03

  So even though the grief does emerge and that comes and I hold that. I think of what I've done and I think of I woke up every morning trying to do my best. I didn't wake up one morning and be like, I'm gonna mess this day up. That's right. So I must be where I'm supposed to be. And I don't know, sometimes I think of all of the things I've done, the courage that I've had to have and what I've had to learn how to navigate as a single person with no one to hide behind. Yeah. And it's built a really beautiful experience around me and I have incredible friends. You do.

• 23:46Craig Robinson?

  Well, this is a good segue to get to our question.

• 23:48Speaker 03

  Let's do it.

• 23:49Craig Robinson?

  Especially the talking about dating and meeting people. And we have a great question. So Natalie, our producer, is going to be the question for. Make sure your mic works over there. Is it working?

• 24:01Speaker 03

  I think we're good.

• 24:02Craig Robinson?

  All right.

• 24:02Speaker 03

  Yeah, we're good. I'm excited.

• 24:05Speaker 04

  Hi, Michelle and Craig. My name is Ronan and I'm 41 years old. I've got a question about that big frustrating topic, dating. More accurately, I should say, how not to date. Let me explain. Throughout my 30s, I was in and out of relationships. One was very fruitful. It lasted several years, but in various respects of our lives, the timing just did not align. So we ended up splitting up. Since then, I've found myself in relationships that have been very clearly unsuccessful. One woman's creative and professional interests totally matched mine, but we fought constantly. Then I was with a woman who was great. Our leisure interests

• 24:48Speaker 04

  were similar. Her family was great, but I was just not that into it. Something was missing. Most recently, I ended up in a longer term relationship that my friends at least would call toxic. We had great chemistry and I was really in love with her, but she struggled with sustained intimacy after a recent divorce. And as a result, I got myself caught in a pretty regular cycle of hurt. Since then, my dating has been a mess. I've been distracted by women I simply find attractive, but who otherwise clearly are not a match. And in the meantime, I still find myself thinking about my last relationship.

• 25:31Speaker 04

  So this brings me back to the start of my question. My closest friends are telling me the one thing I need now is to not date. They tell me if I can figure out how to be happy on my own, I'll have a better chance of finding happiness with someone else. The thing is, I am not totally convinced by this. I enjoy dating, but I also understand that what I'm doing clearly is not working. So what in the world would you say to a guy like me? Are my friends right? Should I try to enter into a period of being single by choice? How could I actually benefit from being single if I ultimately really want a partner and family? And if it is helpful, what tips do you have to help me put this period of non-dating into

• 26:16Speaker 04

  practice and to make it stick? Thanks for your advice, Ronan.

• 26:22Speaker 03

  It's a great question.

• 26:23Michelle Obama?

  Yeah, and it's interesting coming from a 40-ish man.

• 26:28Speaker 03

  Yeah, I like it.

• 26:29Michelle Obama?

  Because men can marry when they choose to, just like.

• 26:31Speaker 03

  Well, yeah, I thought that was so interesting what you said. When you asked Craig that question, I thought, I think it's timing.

• 26:37Michelle Obama?

  Yeah.

• 26:37Speaker 03

  Yeah. That when a guy feels they're ready, then it, who's in front of you.

• 26:41Michelle Obama?

  Right.

• 26:42Speaker 03

  Just crazy.

• 26:42Michelle Obama?

  Mm-hmm.

• 26:43Speaker 03

  Yeah.

• 26:43Michelle Obama?

  Yeah.

• 26:44Speaker 03

  It's crazy.

• 26:44Michelle Obama?

  It's so crazy.

• 26:45Speaker 03

  It is crazy. And then it takes your second marriage to figure out you need to be discerning.

• 26:49Michelle Obama?

  For some people, like they don't go forth or they never figure it out.

• 26:53Speaker 03

  I know.

• 26:53Michelle Obama?

  It's fascinating.

• 26:55Craig Robinson?

  My technique for the second one, I thought was pretty good.

• 26:58Speaker 03

  I think that is really, I thought that was really helpful for other people to hear. The other thing I'm curious is, is that cultural? That men, it's timing? Or is it, I don't know, it's nature or nurture?

• 27:11Michelle Obama?

  Yeah, yeah. I think a lot of it is cultural, right? We grow up waiting to be choo- chosen, you know? At the school dance, you don't get to dance, or at least in our generation, you didn't get to dance if somebody didn't ask you to dance.

• 27:26Speaker 03

  Yeah, and then if you are the chooser, then men are like, you're aggressive.

• 27:30Michelle Obama?

  Oh, my gosh, there wasn't any choosing.

• 27:32Speaker 03

  Well, now for my generation.

• 27:34Michelle Obama?

  Yeah.

• 27:34Speaker 03

  Or I don't even know my generation for me.

• 27:36Michelle Obama?

  Yeah, yeah.

• 27:38Craig Robinson?

  Can I give you just a little bit of a different thought process behind it?

• 27:42Michelle Obama?

  That's why you're here.

• 27:44Craig Robinson?

  Imagine as a 17 year old and you're walking into a sock hop, which I just use for effect, but a dance, a party.

• 27:55Michelle Obama?

  But there are a lot of kids going, what, what is that? What are your socks have to do with anything?

• 28:00Craig Robinson?

  You go, but we used to have these sock hops or it's a school dance. So imagine you're 17 years old and there's a bunch of girls in there and you go ask somebody to dance and they say, no, thank you.

• 28:11Michelle Obama?

  Oh, terrible. Yeah. Yeah.

• 28:13Speaker 03

  Heartbreaking.

• 28:13Craig Robinson?

  And then you go to ask the next person and they say, no, thank you.

• 28:16Michelle Obama?

  Oh, no, I don't like this.

• 28:17Craig Robinson?

  But that's how it was.

• 28:19Michelle Obama?

  Yeah, that's hard. That's very hard.

• 28:20Craig Robinson?

  That's how it was. So the question you have to ask yourself as a guy is, do I just take what I have or do I take the chance of asking the next person and they say no?

• 28:32Michelle Obama?

  Yeah, the courage. Yeah.

• 28:33Craig Robinson?

  That's, that's real. That's real. So.

• 28:37Michelle Obama?

  It's an important perspective for sure.

• 28:39Craig Robinson?

  Yes.

• 28:40Michelle Obama?

  And it, and it is hard, but ultimately you choose, right? It's scary, but you know, so imagine the girl who is standing in the same sock hop with her shoes off now all embarrassed because she's standing in her socks.

• 29:00Craig Robinson?

  See what I have to put up with?

• 29:02Michelle Obama?

  I have, I have four siblings. Waiting to be asked and people are just passing her by, you know? And they're a bunch of shy boys, not even trying. Whereas a guy can decide that the decision is still a man's to make.

• 29:20Craig Robinson?

  Right.

• 29:20Speaker 03

  Not, is it though, always? I just think culturally that is what we say. Yes.

• 29:25Michelle Obama?

  I think culturally, that's what I was saying. The, the original question was, is it nature or nurture? I, I think a lot of it is the culture.

• 29:33Speaker 03

  Yeah.

• 29:34Michelle Obama?

  That gives that power.

• 29:35Speaker 03

  I, I agree.

• 29:36Michelle Obama?

  To men. Now it's a difficult power to have because with power comes responsibility and hurt and risk and all that. But.

• 29:44Speaker 03

  You know, even to this day, as you said, Tracy, if a woman crosses that dance floor to ask, she's aggressive.

• 29:52Michelle Obama?

  Oh, oh, oh, oh.

• 29:53Speaker 03

  It's an unattractive quality. So now I either wait to be to dance or I don't dance at all.

• 30:00Craig Robinson?

  I don't necessarily agree with that.

• 30:02Speaker 03

  Okay.

• 30:02Craig Robinson?

  And I also would say, as a boy or a young man, if a woman walked across the floor and asked me to dance, it was no way I was gonna say no.

• 30:13Speaker 03

  Well, I think, obviously, there's all different kinds of people. There's all different ki-- I mean, and you know, then we are not even entering into the gender fluidity within this conversation. That is so much a part of what the younger generation is making sense of. And I think they're actually doing that really beautifully.

• 30:30Michelle Obama?

  I do, too.

• 30:30Speaker 03

  And I've learned so much from the gender conversation and how it's expanded. I've learned so much about myself and what are the expectations that I didn't know were expectations about being a woman? That I'm like, oh, I don't need to own that because I just thought that was a given. But now I know it's not, you know? But I think the societal norm, yes. I mean, I had a guy say to me recently, yeah, you can't make a man do anything he doesn't want to do. But culturally, you can make a woman do a lot of things she doesn't want to do because we're trained culturally to acquiesce in that way, that that's our role, that we are... But I mean, this guy Ronan, I love the question because, first of all, what I'll say to Ronan is, no one knows you better than you.

• 31:15Michelle Obama?

  That's right.

• 31:16Speaker 03

  And your friends can have all the suggestions in the world, and some of them might be helpful ones, and some of them might be ones you want to consider. And then I think the thing that you have to do is ask yourself, does that feel right for me? Does that really feel like what's gonna get the growth to happen?

• 31:31Michelle Obama?

  Yeah.

• 31:32Speaker 03

  And sometimes not dating helps people discover that. And sometimes dating is the thing that helps people discover that.

• 31:39Michelle Obama?

  Well, and it's interesting when, I think, to your point, Craig, when you were, you had your 32 list item, that was all about Kelly, right? I mean, and that's sometimes what we do.

• 31:55Michelle Obama?

  Forget you. I think that's what a lot of people do. It's like, there's a list of things that I need in the other person.

• 32:01Craig Robinson?

  Right.

• 32:02Michelle Obama?

  And I'm, and, and some of the, a lot of them are superficial, like height and career and income and what school you went to, right? But it's all about the other person meeting a checklist. What Ronan's friends are suggesting and what I agree on is like, okay, there's that list about the other person, but what's your list? What is your 32-point list about yourself that you need to explore? And I think a lot of men.

• 32:34Speaker 03

  Don't.

• 32:34Michelle Obama?

  And I, I hate to generalize like that, but you know, so many women are self-reflective in our groups. We, we live in conversation. We live in a social world where we're constantly analyzing ourselves and each other in our conversations. This is the dialogue of women and men aren't doing that as much. I think the younger generation is doing it more.

• 32:58Speaker 03

  Yeah, I do see a lot more of it. I see a lot of it online and I really celebrate it. I think it's beautiful to see men have these deeper conversations about who they are and what they want. But the norm is no. And then the other thing to me is the invitation, right? It's like, yes, that's the cultural norm, but the invitation is really to remind everyone, men and women, to take into account who they are. And what is important to you? You know, is, is somebody's height the most important thing to you? And why?

• 33:26Michelle Obama?

  Why?

• 33:27Speaker 03

  Is it because of what other people see? Or is it because of you? You know what I mean? Like, what is it? And I think those reflective questions not only help you in dating, they just help you in life.

• 33:37Craig Robinson?

  So let's help, Ron. What are some of these questions he should be asking himself?

• 33:42Michelle Obama?

  Well, you know, just like in developing your life, when I talk to young people, it's like, who do you want to be? What do you care about? And, and not what do you want to do? Not what title you want to have, but how do you want to show up in the world? What's important to you? Is it kindness? Is it empathy?

• 34:03Speaker 03

  Is it money?

• 34:04Michelle Obama?

  Is it money? Yeah, for some people it is. For some people it's security, financial security. Some, it's emotional security.

• 34:14Speaker 03

  Is it, is it important for honesty?

• 34:17Michelle Obama?

  For, for me, for example, like I knew that. You know, you date enough people, you date people that just cheat. Right? And one thing I learned, luckily, I learned it soon, I realized that cheating, if I was dating a cheater, that had nothing to do with me. You know, because like, I am not inherently a cheater or a liar. I mean, I would never, I would rather just look somebody in the face and say, we should break up because I'm thinking about dating somebody else. And I'm not going to hold you hostage while I go experience stuff. So I had to pick somebody who had the same values about that as I do. Right? I didn't want to be married or date somebody that I have to worry about, who are you texting? What's on your phone?

• 35:02Speaker 03

  Where that trust is not an anchor.

• 35:04Michelle Obama?

  That trust is not there. And, and because it was important to them, not because it was important to me.

• 35:10Speaker 03

  But they were the same.

• 35:11Michelle Obama?

  That they, that they had the same quality, you know? That was way more important to me than what career, what, you know? Because I had dated people who were broken, in my opinion, broken in that way. And it's like, that's not fun to me, you know? Guessing whether my partner is faithful. Like, some people are, are good with that game.

• 35:32Speaker 03

  Yes, yes, some people that engages their chemistry. I don't know. And, and I have no judgment, really. Like, there's things for people. Everybody has different values around those things and what's important. Some people don't want deep conversation.

• 35:46Michelle Obama?

  Yeah, yeah.

• 35:46Speaker 03

  Some people, that is not their thing. It feels invasive. It feels uncomfortable. Some people do, you know? I also think for Ronan, um, I have come to really know that there's a big difference in somebody that I am looking at dating as a partner and somebody that's somebody to enjoy and take what I like and leave the rest.

• 36:07Michelle Obama?

  Yeah.

• 36:08Speaker 03

  And I learned, as I've gotten older, like, chemistry is not a relationship.

• 36:14Michelle Obama?

  Ooh, say that again.

• 36:15Speaker 03

  Chemistry is not a relationship.

• 36:17Michelle Obama?

  Yes.

• 36:17Speaker 03

  And love does not always include chemistry.

• 36:21Michelle Obama?

  Yes.

• 36:21Speaker 03

  And I'm somebody who wants both. Now, everybody's not like that. Some people are, really don't want a, a sort of the passionate chemistry of, you know, intimate, um, physical energy. That's not their thing.

• 36:36Michelle Obama?

  Yeah.

• 36:37Speaker 03

  And you don't want to be in a relationship with somebody who that's their, one of the ways they communicate love.

• 36:42Michelle Obama?

  Yeah.

• 36:42Speaker 03

  You know? Like, for example, I have Um, male friends. I have one that we literally text and it's not flirting. And it's all clothes.

• 36:54Michelle Obama?

  Yeah.

• 36:55Speaker 03

  And fashion and shopping.

• 36:56Craig Robinson?

  Oh, all clothes.

• 36:57Speaker 03

  And it's like a version of a relationship. He's the sexiest little thing.

• 37:01Michelle Obama?

  Mm hmm.

• 37:02Speaker 03

  He's young.

• 37:03Michelle Obama?

  Yeah.

• 37:03Speaker 03

  There's never been anything physical.

• 37:05Michelle Obama?

  Right.

• 37:05Speaker 03

  But we have this amazing like exchange that happens all the time.

• 37:10Michelle Obama?

  And I don't have that with my husband.

• 37:11Speaker 03

  No, no.

• 37:12Michelle Obama?

  I, I, that sounds fun.

• 37:14Speaker 03

  But that's fun, right? It's like so fun and I'm single. Then, then I have, I have a friend I go to the movies with. You know what I mean? And then there's people that so.

• 37:22Michelle Obama?

  Yeah.

• 37:22Speaker 03

  And there's, and obviously if I end up in a relationship with someone, those probably will not continue.

• 37:27Michelle Obama?

  Yeah.

• 37:28Speaker 03

  You know, those different things, but my friendships will continue. Cause you also can't expect your partner to be everything.

• 37:35Michelle Obama?

  That's right.

• 37:35Craig Robinson?

  All right. So this is perfect. So what, you know, how do we help Ronan become a better, a better subject for women? How, how do we help him make himself into a more attractive?

• 37:49Speaker 03

  Well, I think he sounds like he's attractive. He's having no problems dating. So what I'll say.

• 37:54Craig Robinson?

  But he's not, it's not sticking.

• 37:55Speaker 03

  Yeah, but that could be timing.

• 37:57Michelle Obama?

  That could be timing.

• 37:58Craig Robinson?

  Okay, all right.

• 37:59Michelle Obama?

  That could be him, you know, that could be him just not choosing. He may not be ready to really settle down.

• 38:05Speaker 03

  The other big thing I'm gonna say, look, I'm 52. I don't know. You know what I mean?

• 38:10Michelle Obama?

  Well, this program is, it's in my opinion. You don't have to know. We just have our deeply held opinions about Ronan's life.

• 38:18Speaker 03

  Exactly. But this is what I'm saying. I, I might not meet a partner.

• 38:24Michelle Obama?

  Yeah, okay.

• 38:25Speaker 03

  I'm saying, like, I know there's this assumption, right? And the assumption is if you don't, there's something wrong with you. I don't agree.

• 38:33Craig Robinson?

  I, I, I agree with you not agreeing with that.

• 38:35Speaker 03

  You know what I mean? Like, I'm just like, no, I don't, that's, no.

• 38:38Craig Robinson?

  Right.

• 38:38Speaker 03

  I'm, I'm a great match and a great catch and all those things, but I also am gonna wait for the right person. So to Ronan, I would say, let yourself own the fact that you want a relationship. And you are gonna do all the things you know how to do to walk towards that. And if it doesn't, if you don't find the right person, it's not a reflection of you.

• 39:01Michelle Obama?

  Yeah.

• 39:02Speaker 03

  If you're doing all the right things, you know what I mean? Like, I think that's the first thing I would say to Ronan. The second thing is, ask yourself the question, is dating helping you get towards what you want? Or is it actually distracting you because there's enough drama? That you're not having the courage to say, this is what I want. I had a friend who was dating recently and the guy is out of a divorce and there's just some stuff going on. And they really like each other, but he's kind of in a hallway. And she said, which I thought was the most courageous and beautiful thing, why don't you call me when you're out of the hallway?

• 39:38Michelle Obama?

  Yeah.

• 39:39Speaker 03

  You know?

• 39:39Michelle Obama?

  When you find a room.

• 39:40Speaker 03

  Yeah, when you find a room and like, if you still think I'm somebody that could be in that room with you, then give me a call. I mean, I said to someone I was dating recently, like, I've come to realize that you are not a loving match for me. As much as I love you.

• 39:54Michelle Obama?

  Yeah.

• 39:55Speaker 03

  And so I'm gonna-

• 39:56Craig Robinson?

  That is a cold, nice, cold-blooded cut right there.

• 40:01Speaker 03

  See, I thought, I'm all like, that's so true.

• 40:04Michelle Obama?

  I know, right?

• 40:05Speaker 03

  Crazy like that, it's Mr. Nice Guy.

• 40:08Michelle Obama?

  I didn't hear from him for a while.

• 40:10Craig Robinson?

  I bet. He's still trying to figure that out.

• 40:13Speaker 03

  Yeah, well, he made his bed before when he wasn't showing up the way he should have. I gave him enough tries. And the crazy thing is for me, when, it takes a lot for somebody to get inside my heart and feel safe. Once you get in there, it's so hard for me to get you out. And I have to really give myself time. And that's the other thing I would say to Ronan about him sort of pining around this old relationship. Remember that in memory, you remember the good stuff.

• 40:35Michelle Obama?

  That's right.

• 40:35Speaker 03

  So it's not always the full picture. There's a reason that didn't work and you can trust that. And the right relationship, there's nothing you can do to make it stop. Like, it will resurface itself if it's meant to be.

• 40:48Michelle Obama?

  Well, that's the, I think that's really great, solid advice. I think there are a lot of people who- Put too much pressure on trying to find everything in one person. I don't know if that's Ronan's issue. But if it is, I'd encourage him to, you know, be a little more open and to understand that relationships are long and there are also ebbs and flows, right? So I think sometimes people who date don't realize that, you know, in long-term relationships, you're gonna, you're gonna have deep, deep dips and you're gonna have- You're gonna have a bad year. You're gonna have a bad, I tell people and folks think that this is harsh. It's like, you're gonna have a bad decade. Yeah.

• 41:29Michelle Obama?

  You know, I mean, I've been married to my husband for 30-plus years. I mean, the truth is, if you add it all up, even the year, having-

• 41:37Craig Robinson?

  Yeah.

• 41:38Michelle Obama?

  If, if the odds were, you're gonna be married to your partner for 50 years and 10 of those years could be bad, you know? That's-

• 41:47Craig Robinson?

  You'd sign up for it.

• 41:47Michelle Obama?

  You'd sign up for it.

• 41:48Craig Robinson?

  You'd sign up for it.

• 41:49Michelle Obama?

  You know, and that's really how it works out. That's the reality of it. The reality is, is that if you choose to have a traditional marriage and you have kids, let me tell you, the years of one to 13 will be bad for you as a, an adult, you know? Because it's beautiful, but they'll- But it's, yeah. They'll take you for a loop and you love them and you don't wanna hate them because they're cute, so you're gonna be mad at the person who is sitting next to you, the other adult. The one who helped you make it. The one who helped you make it, you know? So that's, that accounts for just a decade, right? I think people don't think about that as they date because they're trying to find the

• 42:31Michelle Obama?

  match that where all those 30 years are gonna be blissful. Yeah, that's crazy. And it's like, that's just not gonna happen. Can I just ask what some of the 32 things on the list were?

• 42:41Craig Robinson?

  Yes.

• 42:41Michelle Obama?

  Of the questions?

• 42:42Craig Robinson?

  Yes, you can.

• 42:43Michelle Obama?

  I'm just so curious.

• 42:44Craig Robinson?

  Yes, you can.

• 42:44Michelle Obama?

  Is that okay? Is that valid?

• 42:45Craig Robinson?

  It's okay.

• 42:46Michelle Obama?

  Is that a valid question? You're okay to answer that? That is so good.

• 42:48Craig Robinson?

  It is good. It is good. You just-

• 42:50Michelle Obama?

  It might help Ronan.

• 42:51Craig Robinson?

  It might help Ronan.

• 42:52Michelle Obama?

  And me. Yeah, I'm trying to remember what they were.

• 42:55Craig Robinson?

  So-

• 42:56Michelle Obama?

  What was number, item 30?

• 42:57Craig Robinson?

  So I, I can, I guarantee you Kelly still has the list.

• 43:01Michelle Obama?

  Oh, that's fantastic. We should get her on the phone.

• 43:04Craig Robinson?

  It was, it was, it was significant. But she has this one thing that I didn't have on my list, but I would put on my list now, is are you comfortable with me being able to stand alone in a room?

• 43:22Michelle Obama?

  Do I say that again?

• 43:24Craig Robinson?

  Are you, are you comfortable with me being able to stand alone in a room? So to your point, you have this full life and you have this aura about you that if, if, we're going somewhere, and the same with you, we go into a room, we might not be right next

• 43:40Michelle Obama?

  We're not gonna be coupled to coupled.

• 43:41Craig Robinson?

  We're not gonna be coupled to coupled.

• 43:43Michelle Obama?

  You go one in.

• 43:43Craig Robinson?

  Are you okay with me standing alone? Cause I can stand alone. I was like, oh, okay.

• 43:48Michelle Obama?

  I love that question. So that was her question to you or your question to her?

• 43:53Craig Robinson?

  That was one of her questions to me.

• 43:55Michelle Obama?

  That's a great question.

• 43:56Craig Robinson?

  That wasn't, that was the one that was, that was not a category.

• 44:00Michelle Obama?

  I'm gonna throw that at one of the people I'm dating right now.

• 44:02Craig Robinson?

  Yes.

• 44:03Michelle Obama?

  Look out, mister, whoever you are.

• 44:05Craig Robinson?

  And I said, it's so important to me, especially the way my family is, for you to be able to stand alone. So that's a great one.

• 44:13Michelle Obama?

  Yeah.

• 44:14Craig Robinson?

  And then there were sort of the-

• 44:16Michelle Obama?

  That's a really good one.

• 44:17Speaker 01

  I love that question, actually.

• 44:18Craig Robinson?

  And then, and then the one that we spent the most time on were, what are your deal breakers? What, what is it that you can absolutely not stand? So I can make sure that none of them are like my favorite thing to do.

• 44:31Michelle Obama?

  Yeah, that's really smart.

• 44:32Craig Robinson?

  Yeah, yeah, and, and I will tell you, this was a-

• 44:36Michelle Obama?

  I just like the way you put it though, because you know, it's, it's sort of innocently sweet and it's not so hard over the head. Like, can you stand alone in a room?

• 44:44Speaker 01

  That's why I like the question, cause I would ask that all wrong.

• 44:47Michelle Obama?

  Right, that's just the thing.

• 44:49Speaker 01

  I would ask that same question.

• 44:51Michelle Obama?

  Are you an insecure trifling ass?

• 44:52Speaker 01

  That is exactly right.

• 44:53Michelle Obama?

  Are you so insecure?

• 44:54Speaker 01

  Yeah.

• 44:55Michelle Obama?

  That you can't handle a strong-

• 44:56Speaker 01

  Are you uncomfortable with my bigness?

• 44:57Michelle Obama?

  You know, and then-

• 44:59Speaker 01

  I've been asking all wrong. He would be squashed from the start.

• 45:02Craig Robinson?

  Cause I am a boss, I am a boss.

• 45:04Speaker 01

  I'm a boss, are you okay being the-

• 45:06Michelle Obama?

  Can you level up? Can you level up? And then he's running away going, I don't-

• 45:12Speaker 01

  She's aggressive.

• 45:15Speaker 03

  Yeah, that was really helpful.

• 45:17Michelle Obama?

  Yeah, that's a good way to think about it.

• 45:20Craig Robinson?

  And the one thing, to bring it back to Ronan, is it actually better for Ronan to learn more about himself by not dating than dating a whole bunch of people? Because in the question, he's asking the question, should I just not date?

• 45:37Speaker 03

  Well, I think it depends because I don't think we have enough information from Ronan, right? Like, when he says distracting, what kind of distracting? So that's why I posed the question back to him of, you have to ask yourself some questions to figure out, is that the right advice for you?

• 45:53Michelle Obama?

  Yeah.

• 45:53Speaker 03

  Are you learning enough from dating that's actually giving you the right information about yourself? Or is the dating actually taking you off course? Because you're getting invested in the drama of things aren't working out or are working out.

• 46:05Michelle Obama?

  Tracy, I think that's a good point for everyone. Are people dating with intentionality? You know, to learn something, right? Or people just out there? And if you're not reflecting on why you picked somebody, you know, why the dinner went well, you know, why you laughed, and it is just happening to you without, you know, for men and women, for anybody of any sexual preference, it's like doing some self-assessment through the process, I would encourage, you know? Because we're not taught to do that either in dating.

• 46:42Speaker 03

  I agree.

• 46:43Michelle Obama?

  You know, there's no guide.

• 46:44Speaker 03

  Did he call again?

• 46:45Michelle Obama?

  Exactly. You know, where did you go? Where did he take you? And are we asking?

• 46:49Speaker 03

  What does he do?

• 46:50Michelle Obama?

  Right, are we asking questions of how do you feel? Why did you feel that way? Why did this relationship end? I think that may be what Ronan's friends are suggesting, and he can do that, and he can do both.

• 47:02Speaker 03

  Yes, he can.

• 47:03Michelle Obama?

  He can date and can, but be more reflective about the process. And I think that's true for everyone.

• 47:10Speaker 03

  Yeah.

• 47:11Michelle Obama?

  If you want to have a partner, you've got to know yourself.

• 47:14Speaker 03

  Yep.

• 47:15Michelle Obama?

  It's dating and having an internal conversation.

• 47:18Speaker 03

  Agreed.

• 47:19Michelle Obama?

  About why, your whys, your motivations, your history, your fears. What are you, you know, what are you mimicking? You know, like Craig, you were imitating what? You thought your mom and dad had, and you did that more than me. I was more like, I'm, I don't know if I want to be like them. You know, loved them, loved their marriage, but I, I, I didn't date for, I want to do what my mom and dad did. I think Craig, you're more that kind of, this is the way it works.

• 47:50Craig Robinson?

  It was, it was a, a pattern or a strategy. The strategy is you go to college, you find a job, you have some single life. And then you get married. And I was just sort of checking off the, the, I was, I was following a strategy and that's just not.

• 48:11Michelle Obama?

  Or an expectation to do that. I don't want any, I want this generation of young people to be more thoughtful.

• 48:18Speaker 03

  Yeah. And thoughtful from an internal compass is my thing. I always ask myself, when I leave any situation, date included, how do I feel after? Do I feel, because sometimes you can think it's really nice in that moment and you leave. And I was like, wait, why do I feel small? Why do I feel more insecure? Or do you feel good about yourself? Another question I, I do like to ask people is, how do you argue?

• 48:45Michelle Obama?

  Oh, that's a good one. Yeah.

• 48:46Craig Robinson?

  That was on the list. That was on the list.

• 48:49Michelle Obama?

  That was 12.

• 48:50Craig Robinson?

  Yeah, that was on the list. That's a good one.

• 48:52Speaker 03

  It's a good one, you know, because like my siblings, we all, there's a way that my family argues that I'm comfortable with. And I've been, because I get loud and then it's done. Like I'm so straightforward. I'm not somebody who's going to like hold it, like I'm going to say it. For some people, that's terrifying.

• 49:07Michelle Obama?

  Yes.

• 49:08Speaker 03

  It's terrifying and sort of sends them into another place. So those are, I just think all those kinds of questions. And asking them both of the other person and of yourself.

• 49:21Michelle Obama?

  And it's not always a deal breaker. It's just something to be aware of because it will be a thing that you will need to work on in the relationship. That's what makes relationship, marriage, partnership so hard because you are taking. Two independent people with a whole different set of experiences and saying, you know, forever and ever, amen. Marriage is hard.

• 49:45Speaker 03

  Yeah.

• 49:45Michelle Obama?

  And it is reasonably hard, you know?

• 49:49Speaker 03

  It's the right kind of hard.

• 49:51Michelle Obama?

  It's the right kind of hard, but don't get upset when it's hard, you know?

• 49:55Speaker 03

  Well, I mean, you know, social media has made a myth of so many things because life requires you to show up.

• 50:02Michelle Obama?

  That's right.

• 50:03Speaker 03

  And if you want anything out of it, it's gonna be work, you know? And relationships included. Someone told me this great just metaphor of imagine that the people you're closest to, you're gonna step on each other's toes. And so how do you work out the stepping on toes? Do you just blame them?

• 50:20Michelle Obama?

  That's right.

• 50:21Speaker 03

  Or do you figure out how to not step on each other's toes? Or is that just the nature of what a relationship brings? And then how do you work those things through and work those things out?

• 50:32Michelle Obama?

  And it's important for Ronan to understand that it's work.

• 50:35Speaker 03

  Yeah.

• 50:35Michelle Obama?

  Because sometimes, maybe for men, or if they can be choosers, or people in general, they think something, that there's something wrong in the dating process. And it's like, nah, it's just, you know, what it means to be with somebody else.

• 50:50Speaker 03

  Yeah.

• 50:50Michelle Obama?

  It's complicated, it's hard, it requires compromise, it requires you to change and adapt all throughout the process, you know? You can't just come in and say, well, this is who I am, you know? And this is, these are my habits. So some of the list is important, but when you couple, you will not be able to find the exact right person who just balances you on all those 32 points.

• 51:14Craig Robinson?

  Exactly.

• 51:15Michelle Obama?

  It's just, you know, then you will be alone and that's okay, too.

• 51:19Speaker 03

  Or you're gonna try and date yourself, which you don't wanna do.

• 51:22Michelle Obama?

  And that won't be fun because you'll find out all the worst parts of yourself and you will be divorced from yourself.

• 51:28Speaker 03

  Do you have this, you as the man in your relationship, as, since we've been talking about it from our perspective, do you feel that you have continued to grow in your current marriage and that it asks that of you?

• 51:42Craig Robinson?

  Absolutely, because it sounds like the list was my list, but the discussion that it brought continues to happen to this day. That's what's so beautiful about it because I can tell the growth comes because when we go to dinner on our date nights. We're talking as if we have not had just met. Like, we are always talking. And it's, and so I've just gotten better at being in a relationship. And, and, and that's what I.

• 52:14Speaker 03

  That's, that's a really nice thing to say. Like, I've gotten better at being in a relationship.

• 52:18Craig Robinson?

  That's why, in our opinion, we're, in, in, in my opinion, the show is like, let's teach everybody how to get better at this.

• 52:25Michelle Obama?

  Or to know that it's something, it's an important muscle to build.

• 52:29Craig Robinson?

  Perfect time to give Ronan some takeaways.

• 52:33Speaker 03

  Okay, okay.

• 52:34Craig Robinson?

  And, and I'm gonna.

• 52:36Speaker 03

  You're the master takeaway.

• 52:37Michelle Obama?

  You took notes.

• 52:38Speaker 03

  Come on, code, do it.

• 52:39Michelle Obama?

  Tell us.

• 52:40Craig Robinson?

  The self-reflection has to be at the top.

• 52:42Speaker 03

  Yes.

• 52:43Craig Robinson?

  Self-reflection has to be at the top. And Tracy, you said something that was really interesting. Do you even want to be, have a connection with?

• 52:53Speaker 03

  Chemistry, chemistry and love, yeah.

• 52:55Craig Robinson?

  Chemistry and love? Or is this just a, I'm not in love with you?

• 52:59Speaker 03

  Mm-hmm.

• 53:00Craig Robinson?

  Kind of thing?

• 53:01Speaker 03

  What's important to him in a relationship?

• 53:03Craig Robinson?

  What's important to him? And then the third thing that I had, and Meech, you said this, is you have to do the extra work. In, in, in not only being in the relationship, but trying to find a relationship.

• 53:18Speaker 03

  Mm-hmm. And I, can I reframe that?

• 53:20Craig Robinson?

  Yes, you can reframe that.

• 53:21Speaker 03

  So, let's just call it the work. Cause it's not extra work. That's just the work it takes.

• 53:26Craig Robinson?

  Okay.

• 53:26Speaker 03

  Yeah.

• 53:27Craig Robinson?

  Do the work.

• 53:27Speaker 03

  Yeah.

• 53:28Craig Robinson?

  Do the work.

• 53:28Michelle Obama?

  And I have one last thing. It's, uh, and there's no one right way to live a life. I mean, maybe, Ronan, you don't choose a life partner. Or it doesn't happen, or you don't find it. There's so many ways to be happy, and it doesn't just look like marriage, two kids, and a house. There's so many examples of people who live full, wonderful lives. That aren't following the quote unquote, "traditional" path. And I just want Ronan not to force something that isn't there.

• 54:06Speaker 03

  Yeah.

• 54:06Michelle Obama?

  It's like stars aligning. It may not happen. So, now the work is, how are you happy with the life that's right before you? That's what I want for my daughters.

• 54:16Speaker 03

  Yeah.

• 54:17Michelle Obama?

  That's what I'm raising them to be, is like, how are you happy with how, like, is working out right at this moment? So that you're not living in regret, or living in, I wish. Or holding up your life, you know? So when you're waiting for it to happen, you know, in the meantime, Ronan, live.

• 54:36Speaker 03

  Yeah.

• 54:36Michelle Obama?

  Live, grow, adapt for your own self.

• 54:41Speaker 03

  Yeah, and if there are those things that you are like longing to do with a partner, are there versions of that you can do with yourself? Which is, which is the thing that I have really discovered in my life. I'm like, all right, so how can I do that on my own? While still dating.

• 54:55Michelle Obama?

  Mm hmm.

• 54:56Speaker 03

  Well, Tracy. What a fun conversation.

• 54:58Michelle Obama?

  I love you.

• 54:59Speaker 03

  I love you right back.

• 55:00Michelle Obama?

  Yeah.

• 55:01Speaker 03

  This was so nice.

• 55:02Craig Robinson?

  This was so nice. Thank you for doing this.

• 55:03Michelle Obama?

  Yeah, yeah, and you know, your vulnerability, your willingness to share, be open. Always refreshing.

• 55:11Speaker 03

  Thanks.

• 55:11Michelle Obama?

  So, see ya.

• 55:12Speaker 03

  That's my currency.

• 55:13Michelle Obama?

  That's what you get. You do it. You use it well. Thanks so much.

• 55:17Craig Robinson?

  I'm back soon.

• 55:18Speaker 03

  I will.

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