Dating Should Be about Pursuing Joy with Tracee Ellis Ross

Summary

Podcast Summary: "Dating Should Be about Pursuing Joy with Tracee Ellis Ross"

Podcast Information:

• Title: IMO with Michelle Obama and Craig Robinson
• Host/Author: Higher Ground
• Episode: "Dating Should Be about Pursuing Joy with Tracee Ellis Ross"
• Release Date: April 16, 2025

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Introduction: Embracing Life in the 60s

The episode opens with Michelle Obama and her brother, Craig Robinson, engaging in their signature relaxed and humorous banter. They reflect on their experiences of aging gracefully, sharing personal anecdotes about daily life and relationships. Michelle muses, “We are in our 60s, my friend” (01:07), underscoring a lighthearted conversation about embracing the later stages of life with gratitude and humor.

Airbnb Adventures and Family Dynamics

Michelle and Craig delve into their different approaches to travel and hosting. Craig shares his newfound appreciation for the Airbnb lifestyle, contrasting it with his previous preference for hotels. “But the amenities of having your own place, that's like a house and you can sort of live the way you normally live is much more appealing” (02:30). Michelle humorously teases him about never staying with her, highlighting their playful sibling relationship.

Transition to the Main Topic: Dating

The conversation smoothly transitions to the episode’s main theme: dating. Michelle expresses her enthusiasm, “I love talking about dating because I haven't done it in decades” (04:08). Craig reflects on their upbringing, noting the lack of conversations about dating during their youth. This sets the stage for a deeper exploration of contemporary dating challenges and strategies.

Introducing the Guest: Tracee Ellis Ross

The hosts warmly welcome Tracee Ellis Ross, an award-winning actress, screenwriter, director, and entrepreneur. They highlight her multifaceted career and personal insights, creating an inviting atmosphere for an in-depth discussion on dating and relationships.

Generational Perspectives on Dating

Tracee shares her unique perspective as a modern woman navigating the dating landscape. She discusses the evolution of dating norms and the impact of cultural shifts on personal relationships. “I have to make sure that I'm not subconsciously sending [the girls] these messages about what their life should look like” (22:07), Michelle adds, emphasizing the importance of authentic relationship models for younger generations.

Ronan’s Question: Navigating the Complexities of Modern Dating

The episode features a thoughtful segment where the hosts address a listener’s question from Ronan, a 41-year-old man struggling with unsuccessful relationships and contemplating whether to take a break from dating. Ronan’s dilemma revolves around balancing the desire for companionship with the recurring pattern of toxic relationships.

Advice and Insights: Self-Reflection and Intentional Dating

Michelle, Craig, and Tracee offer comprehensive advice to Ronan, emphasizing the importance of self-reflection and intentionality in dating. Tracee advises, “I think the thing that you have to do is ask yourself, does that feel right for me?” (31:15), encouraging Ronan to assess whether his current dating practices align with his personal growth and happiness.

Craig shares his approach, highlighting the significance of self-awareness: “Self reflection has to be at the top” (52:42). He underscores the necessity of understanding one’s values and what truly matters in a relationship.

Michelle adds a broader perspective, suggesting that happiness does not solely depend on finding a partner: “There’s so many ways to be happy. And it doesn’t just look like marriage, two kids, and a house” (51:19). This reinforces the idea that self-fulfillment is crucial, regardless of relationship status.

Key Takeaways: Building Healthy Relationships

The panel distills the conversation into actionable advice for Ronan and listeners alike:

1. Self-Reflection: Understand your values, desires, and what you seek in a relationship. Ask yourself questions like, “What do I want from a partner?” and “How do I feel after a date?”

2. Intentional Dating: Approach dating with purpose rather than as a means to an end. Ensure that each relationship contributes positively to your personal growth.

3. Setting Boundaries: Clearly define your deal-breakers and non-negotiables. As Craig mentions, knowing your deal-breakers helps prevent unhealthy relationships.

4. Managing Expectations: Recognize that every relationship has its challenges and requires compromise. Embrace the reality that relationships involve both joyous and difficult moments.

5. Embracing Singlehood: Find happiness and fulfillment in being single. This empowers you to enter relationships from a place of strength rather than need.

Notable Quotes:

• Michelle Obama: “We are in our 60s, my friend” (01:07)
• Craig Robinson: “Self reflection has to be at the top” (52:42)
• Tracee Ellis Ross: “I think the thing that you have to do is ask yourself, does that feel right for me?” (31:15)
• Michelle Obama: “There’s so many ways to be happy. And it doesn’t just look like marriage, two kids, and a house” (51:19)

Conclusion: Embracing Growth and Authenticity

As the episode wraps up, Michelle, Craig, and Tracee reiterate the importance of personal growth, authenticity, and intentionality in building meaningful relationships. They encourage listeners to prioritize their well-being and maintain honest communication in their romantic endeavors.

Final Thoughts:

This episode of IMO with Michelle Obama and Craig Robinson offers a rich and engaging exploration of modern dating dynamics. With the insightful contributions of Tracee Ellis Ross, listeners gain valuable perspectives on navigating relationships with joy and authenticity. The candid discussions and practical advice make this episode a must-listen for anyone seeking to enhance their dating experiences and build fulfilling connections.

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Time-Stamped Highlights:

• 01:07: Hosts discuss embracing life in their 60s.
• 04:08: Transition to the topic of dating.
• 22:07: Michelle emphasizes authentic relationship models for younger generations.
• 31:15: Tracee advises on self-reflection in dating.
• 51:19: Michelle highlights diverse paths to happiness beyond traditional relationships.
• 52:42: Craig stresses the importance of self-reflection.

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This comprehensive summary encapsulates the essence of the episode, capturing the key discussions, insights, and advice shared by Michelle Obama, Craig Robinson, and Tracee Ellis Ross. It serves as a valuable resource for those who wish to glean wisdom from this enlightening conversation on dating and personal growth.

Transcript

[Michelle Obama]

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

[Tracy Ellis Ross]

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

[Craig Robinson]

Right.

[Tracy Ellis Ross]

That's just the thing. I would ask that.

[Michelle Obama]

Are you an insecure Trifling.

[Tracy Ellis Ross]

That is exactly right.

[Michelle Obama]

Are you so insecure. Yeah. That you can't.

[Tracy Ellis Ross]

Are you uncomfortable with my bigness?

[Michelle Obama]

That's right. You know, don't ask it. All right.

[Tracy Ellis Ross]

He would be so.

[Craig Robinson]

Because I am a boss. I am a boss.

[Tracy Ellis Ross]

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

[Michelle Obama]

Can you level up? Can you level up? And then he. He's running away going. This place aggressive.

[Craig Robinson]

How you doing?

[Michelle Obama]

I'm doing great. Yeah? Feeling good. Another day alive. We're getting to that age where, you know.

[Craig Robinson]

No, we're not.

[Michelle Obama]

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

[Craig Robinson]

Yeah.

[Michelle Obama]

We are in our 60s, my friend.

[Craig Robinson]

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

[Michelle Obama]

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

[Craig Robinson]

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

[Michelle 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 got to bed early and had plenty of sleep. How's your Airbnb feeling?

[Craig Robinson]

Oh, my gosh.

[Michelle Obama]

Still happy with your situation?

[Craig Robinson]

I'm so happy that I did not go to dinner last night. I left here just to stay in your Airbnb house. In my Airbnb in West Hollywood. And guess who visited me this morning to do their laundry?

[Michelle Obama]

Who?

[Craig Robinson]

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

[Michelle Obama]

Why does she have laundry? How long has she been here?

[Craig Robinson]

Because she works out every day.

[Michelle Obama]

Oh, ok.

[Craig 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.

[Michelle Obama]

Yeah.

[Craig Robinson]

And I think she's going to come stay with me tonight.

[Michelle Obama]

So I'm learning a lot about The Airbnb life. Since you don't do that, you don't.

[Craig Robinson]

Get to do it.

[Michelle Obama]

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

[Craig Robinson]

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

[Michelle 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.

[Craig Robinson]

And I find I've gotten to like it now. So, you know, I was a strictly hotel guy. I wanted maid service every day. I wanted to be able to go down to the bar and not have to drive anywhere. I wanted all that stuff. But then the amenities of having your own place, that's like a house and you can sort of live the way you normally live is much more appealing.

[Michelle Obama]

Well, it sounds like it'd be a good girls trip, a friend gathering session, or, you know, little. But anyway. Well, I'm glad you are comfortable in your Airbnb, mister. So you'll never stay with me ever again? I guess.

[Craig Robinson]

No, that's. It's. It's. I would not.

[Michelle Obama]

Have we been displaced?

[Craig Robinson]

You have not been displaced.

[Michelle Obama]

Oh, good.

[Craig Robinson]

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

[Michelle Obama]

Would I mess up your mojo if I showed up with my motorcade in your house? Driving up the driveway with it?

[Craig Robinson]

Wouldn't mess up my mojo. Might mess up the owner's mojo. It might not mess up.

[Michelle Obama]

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

[Craig Robinson]

Yes. Yes.

[Michelle Obama]

Well, what are we talking about today?

[Craig Robinson]

So we're talking about dating today. And.

[Michelle Obama]

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

[Craig Robinson]

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.

[Michelle Obama]

When we were younger, I felt like I was way more in your business, and I kept my business to myself.

[Craig 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.

[Michelle Obama]

No, that's the problem.

[Craig Robinson]

I got to college, so with.

[Michelle Obama]

With you and these sports, it's like.

[Craig Robinson]

Yeah.

[Michelle Obama]

So spending too much time in the gym?

[Craig Robinson]

Yeah. Yeah. It really was too much time in a gym and focused on my schoolwork, and then I just wasn't.

[Michelle Obama]

But it was. But it's interesting because. All right, so this is the benefits of being the sister 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 JV team.

[Craig Robinson]

Yeah, they were younger versions of.

[Michelle Obama]

Because that was always an important test. 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. You know, also you. And you had this theory about, you know, knowing a person by their on the court behavior.

[Craig Robinson]

Yeah, I can't take full credit for that because I really got it from dad. And what. What dad. 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 Meesh 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.

[Michelle Obama]

That's not true. I've had many a long term boyfriend.

[Craig Robinson]

I wouldn't call those guys boyfriends.

[Michelle Obama]

Oh, my gosh. See? See what I had to go through? You didn't even call. You didn't even want to call my boyfriends boyfriends. None of those guys anymore. Anyway.

[Craig Robinson]

Anyway, so Meish 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 Misha was usually posting up her other boyfriends. She said, at least he's tall. And I was. 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 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. If, if he turns out to be a bad dude, I am not gonna be the one to say. And you say, come on, please. And I finally acquiesced. And so we went and obviously we had a great time playing. And what did you learn about this is what I learned. Aside from the fact that he is tremendously left handed, so he couldn't go right at all. 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 the rest is history. So anyway, we got off the subject and, you know, another one of the reasons why I didn't date was I went to an all boys high school. So it's not like girls are walking down the hallway and you see one like, ooh, want to go to movies or something? It was like crickets.

[Michelle 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. Yeah, you did say that. 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, right?

[Craig Robinson]

No. 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.

[Michelle Obama]

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

[Craig Robinson]

Yeah.

[Michelle Obama]

How do you think your friends think about selecting dating?

[Craig Robinson]

Here's what I will say. And I am dying to get our guest out here because she's gonna be able to help another person referee for sure. This between you and me, but I.

[Michelle Obama]

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

[Craig Robinson]

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.

[Michelle Obama]

Yeah, it's like musical chairs.

[Craig Robinson]

Exactly.

[Michelle Obama]

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

[Craig 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, 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. If it 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 is 30 different things.

[Tracy Ellis Ross]

32.

[Craig Robinson]

32 things that I had individually, that one.

[Michelle Obama]

32 items.

[Craig Robinson]

32 items. She had three. I was like, this ain't gonna work. But after we went through my 32, you know what she said?

[Michelle Obama]

What?

[Craig Robinson]

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

[Michelle Obama]

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

[Craig Robinson]

I was.

[Michelle Obama]

That's how women are. You go from like, I didn't ask any questions. I was just ready to get married to a list of 105 before. But that.

[Craig Robinson]

Well, it worked. It worked because now, I mean, you know everything. I knew everything. She knew everything about me. And so it worked out. Thank goodness. But let's bring out our next guest. And I almost feel like I don't even wanna 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.

[Michelle Obama]

She's just really. She got manners.

[Craig Robinson]

She's just sweet. She's got. Man, she was raging. She's funny. Talking about being fun. She's funny.

[Michelle Obama]

Exactly.

[Craig Robinson]

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

[Michelle Obama]

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

[Craig Robinson]

Oh, man. You let me do my job.

[Tracy Ellis Ross]

I'm sorry.

[Michelle Obama]

I'm sorry. I interrupt.

[Craig Robinson]

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

[Michelle Obama]

Tracy. How are you?

[Tracy Ellis Ross]

I'm so good.

[Craig Robinson]

Like I said family.

[Tracy Ellis Ross]

I do. I do feel like family.

[Craig Robinson]

We got family in the house.

[Tracy Ellis Ross]

Really interesting conversation. And I took some notes. Oh, 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.

[Michelle Obama]

Yes, they Let their guard down.

[Craig Robinson]

They let their guard down and their character comes out.

[Tracy Ellis Ross]

I think I could have used that information. I think I'm a little late on adding that to my list of how to figure out if he's a match. Noted. Now there's still times I'm still single, so.

[Michelle Obama]

Noted. Now there's still time.

[Craig Robinson]

They're breaking his hip trying to play basketball.

[Michelle Obama]

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

[Craig Robinson]

I know.

[Michelle Obama]

I made Barack put his basketball shoes up once he got his lip busted when he was in the White House playing pickup game. Yeah. And I don't think many people realize this. Cause he was definitely in shape, athletic. And I remember because you were at that pickup game.

[Craig Robinson]

Yes.

[Michelle Obama]

And I'm in the White House actually in the doctor's office getting an exam. So they're playing in one of the admin gyms. And we get the call, we hear that the agents are like, you know, renegades coming back. There's been an accident. You know, 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.

[Tracy Ellis Ross]

Yeah.

[Michelle Obama]

People are depending on you, you know, and. And literally he's coming in with a, you know, a gauze thing on his lip.

[Tracy Ellis Ross]

He didn't need stitches or anything.

[Michelle Obama]

He needed like 30 something stitches. I mean, his lip was. I saw it. It was like he took the thing away and I was like, your lip. And he had some major speech. This was probably Saturday. He had some major speech on Monday. This is what I'm saying. You know, you're playing like you're 10 and now your lip is split. So we digress, because no longer can we. Are we dating people?

[Tracy Ellis Ross]

No. But I am.

[Michelle Obama]

Yeah. I was about to say I was like, tracy. Tracy's, you know, my girl. I mean, the tales from the road.

[Tracy Ellis Ross]

And I do bring. I bring stories home.

[Michelle Obama]

She bring back to Michelle's stories. I'm like, what's happened in the last several months?

[Tracy Ellis Ross]

And it's always eventful.

[Michelle Obama]

It's always good.

[Tracy Ellis Ross]

Well, the thing is, I stay open. I'm probably way open. Yes.

[Natalie]

Oh, my God.

[Tracy Ellis Ross]

That sounded so wrong.

[Michelle Obama]

I didn't mean that, Mom. My heart, your family.

[Tracy Ellis Ross]

My heart stays open than it should. Yes.

[Craig Robinson]

Yeah, that was hard.

[Tracy Ellis Ross]

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.

[Michelle Obama]

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

[Tracy Ellis Ross]

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 are 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 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.

[Michelle Obama]

Well, I don't know.

[Tracy Ellis Ross]

And that's different.

[Michelle 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 reharnessing us, you know, whether is it really about.

[Tracy Ellis Ross]

And can that really work rights?

[Michelle Obama]

Can that really work now that women are educated and we're being raised differently? I mean, the truth is, is that men. Fathers are modernized. Right. I mean, mostly. 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. And freedom. And 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.

[Tracy Ellis Ross]

Who believes that her body is his. Ch.

[Michelle Obama]

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

[Tracy Ellis Ross]

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

[Michelle Obama]

Let's stop on that, folks.

[Tracy Ellis Ross]

Oh, my God, we had a great.

[Michelle Obama]

Dinner on that one.

[Tracy Ellis Ross]

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.

[Michelle Obama]

Yes, Parish. This is what I'm saying. Tales from Tracy's.

[Craig Robinson]

It's fun.

[Tracy Ellis Ross]

It's very fun to share.

[Michelle Obama]

Tracy. Tails.

[Tracy Ellis Ross]

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

[Michelle Obama]

There's that.

[Tracy Ellis Ross]

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 did enough of it where I was controlled and felt like I was a possession or whatever those things were, or prize, and I just. I have no interest in it, and I will not do it again.

[Michelle Obama]

I'm sorry.

[Craig Robinson]

No, I was going to say. So it's a generational thing. So it didn't matter how you met them, or is it just kind of.

[Tracy Ellis Ross]

The guys you're meeting? That's obviously a big of a generalization. It's a generalization, but because 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 where I'll be, you know, sitting across the table from somebody and just like. What did you just say?

[Michelle Obama]

What century are you? Like, oh, my God, where's your horse and buggy?

[Tracy Ellis Ross]

Yeah. Like, I'm so sorry.

[Michelle Obama]

Your bedpan. Yeah.

[Tracy Ellis Ross]

For real.

[Craig Robinson]

Chamber pot.

[Tracy Ellis Ross]

Yeah, your chamber pot. Your 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. 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. 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.

[Craig Robinson]

So you're meeting folks in the wild, then?

[Tracy Ellis Ross]

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 level of recognition that they 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 moving up on what it is that I'm looking for as a match. I've had some doozies.

[Michelle Obama]

Yeah. But I just love watching your life because you were modeling so many things. The next phase, how many versions of ourselves we can become at all ages in life, you know, and how to build the life you want, 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 Em, 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 20s. You know, the whole thing about weddings.

[Tracy Ellis Ross]

You know, we talk a lot about that.

[Michelle Obama]

Yeah, it's just like the pre proposal and the bachelorette and pre honeymoon and then the three wedding dresses and the. And you know, have you thought about the amount of money, 32 list items of who you want to marry? Or are you more busy planning, picking out your photographer?

[Tracy Ellis Ross]

Yeah, it's interesting, that whole. I hope that that is starting to dissipate culturally. I really, 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, 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.

[Craig Robinson]

That's a great point for people to hear.

[Tracy Ellis Ross]

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. 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.

[Michelle Obama]

That's right.

[Tracy Ellis Ross]

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. And it's built a really beautiful experience around me. And I have incredible friends.

[Natalie]

You do?

[Craig Robinson]

Well, this is a good segue to get to our question, especially the talking about dating and meeting people. And we have a great question. So Natalie, our producer, is going to read the question for. Make sure your mic works over there. Is it working?

[Natalie]

I think we're good.

[Craig Robinson]

All right.

[Natalie]

Yeah, we're good.

[Tracy Ellis Ross]

I'm excited.

[Natalie]

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

[Tracy Ellis Ross]

That's a great question. Yeah.

[Michelle Obama]

And it's interesting coming from a 40ish man.

[Tracy Ellis Ross]

Yeah. I like it.

[Michelle Obama]

Because men can marry when they choose to. Just like.

[Tracy Ellis Ross]

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

[Michelle Obama]

Yeah.

[Tracy Ellis Ross]

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

[Michelle Obama]

Right. Which is crazy. Yeah, it's crazy.

[Tracy Ellis Ross]

So crazy.

[Michelle Obama]

It is crazy.

[Tracy Ellis Ross]

And then it takes your second marriage to figure out.

[Michelle Obama]

You need to be discerning for some people, like they don't go north or they never figure it out.

[Tracy Ellis Ross]

I know, it's like fascinating.

[Craig Robinson]

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

[Tracy Ellis Ross]

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 such an interesting nature or nurture.

[Michelle Obama]

Yeah, Yeah. I think a lot of it is cultural. Right. We grow up waiting to be 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. Yeah.

[Tracy Ellis Ross]

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

[Michelle Obama]

Oh my gosh. There wasn't any choosing.

[Tracy Ellis Ross]

Well now for my generation, I don't even know my generation. For me.

[Michelle Obama]

Yeah, yeah.

[Craig Robinson]

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

[Michelle Obama]

That's why you're here.

[Craig Robinson]

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

[Michelle Obama]

But there are a lot of kids going, what, what is that?

[Tracy Ellis Ross]

What do your socks have to do with anything?

[Craig Robinson]

You go, but we used to have these sock hops or 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.

[Tracy Ellis Ross]

Oh, terrible.

[Michelle Obama]

Yeah. Yeah.

[Tracy Ellis Ross]

Heartbreaking.

[Craig Robinson]

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

[Tracy Ellis Ross]

Oh, no, I don't like this.

[Craig Robinson]

But that's how it was.

[Michelle Obama]

Yeah.

[Tracy Ellis Ross]

That's hard. That's very hard.

[Craig 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?

[Tracy Ellis Ross]

Yeah, the courage.

[Michelle Obama]

Yeah, that's, you know, that's real.

[Craig Robinson]

It's real.

[Michelle Obama]

So it's an important perspective, for sure.

[Craig Robinson]

Yes.

[Michelle 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.

[Tracy Ellis Ross]

Waiting.

[Craig Robinson]

She's gonna have to put up with.

[Michelle Obama]

I have four siblings waiting to be asked, and people are just passing her by, you know, and there are a bunch of shy boys not even trying, whereas a guy can decide the decision is still a man's to make.

[Craig Robinson]

Right.

[Tracy Ellis Ross]

Is it, though? Always. I just think culturally, that is what I said.

[Michelle Obama]

I think culturally, that's what I was saying. The original question was, is it nature or nurture? I think a lot of it is the culture that gives that power. I agree to men now, it's a difficult power to have, because with power comes responsibility and hurt and risk and all that. But, you know, even to this day, as you said, Tracy, if a woman crosses that dance floor to ask, she's aggressive.

[Craig Robinson]

Oh, oh, oh, oh.

[Michelle Obama]

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

[Craig Robinson]

I don't necessarily agree with that. And I also would say as a boy or a young man, if a woman walked across and asked me to dance, it was no way I was gonna say no.

[Tracy Ellis Ross]

Well, I think, obviously there's all different kinds of people. There's all different kind. 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. I do, too. 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.

[Michelle Obama]

That's right.

[Tracy Ellis Ross]

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 going to get the growth to happen? And sometimes not dating helps people discover that. And sometimes dating is the thing that helps people discover that.

[Michelle Obama]

Well, and it's interesting when I think to your point, Craig, when you had your 32 list item, that was all about Kelly. Right. I mean, and that's sometimes what we do. 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 and 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, and I hate to generalize like that, but you know, so many women are self reflective. In our groups, 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.

[Tracy Ellis Ross]

Yeah, I do see a lot more of it. I see a lot of it online and I really celebrated. 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?

[Michelle Obama]

Why?

[Tracy Ellis Ross]

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.

[Craig Robinson]

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

[Michelle Obama]

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

[Tracy Ellis Ross]

Is it money?

[Michelle Obama]

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

[Tracy Ellis Ross]

Is it important for honesty?

[Michelle Obama]

For me, for example, I knew that you date enough people, you date people that just cheat, right? And one thing I learned, luckily I learned it soon I realized the 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 gonna 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 you texting? What's on your phone? Where did you go?

[Tracy Ellis Ross]

That trust is not there.

[Michelle Obama]

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

[Tracy Ellis Ross]

That they were the same.

[Michelle Obama]

That they had the same quality that was way more important to me than what career, what. Cause 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 good with that game.

[Tracy Ellis Ross]

Yes, yes. Some people. That engages their chemistry. I don't know. 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.

[Michelle Obama]

Yeah. Yeah.

[Tracy Ellis Ross]

Some people. That is not their thing. It feels invasive. It feels uncomfortable. Some people do. You know, I also think for Ronan, 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. And I learned as I've gotten older, like, chemistry is not a relationship. And love.

[Michelle Obama]

Say that again.

[Tracy Ellis Ross]

Chemistry is not a relationship.

[Michelle Obama]

Yes.

[Tracy Ellis Ross]

And love does not always include chemistry.

[Michelle Obama]

Yes.

[Tracy Ellis Ross]

And I'm somebody who wants both now. Everybody's not like that. Some people really don't want sort of the passionate chemistry of intimate physical energy. That's not their thing. And you don't want to be in a relationship with somebody who. That's one of the ways they communicate love. You know, like, for example, I have male friends. I have one that we literally text. And it's not flirting, and it's all clothes and fashion and shopping, and it's like a version of a relationship. He's the sexiest little thing. He's young. There's never been anything physical, but we have this amazing, like, exchange that happens.

[Michelle Obama]

And I don't have that with my husband. No, no, that sounds fun.

[Tracy Ellis Ross]

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

[Michelle Obama]

So.

[Tracy Ellis Ross]

And obviously, if I end up in a relationship with someone, those probably will not continue. You know, those different things. But my friendships will continue. Because you also can't expect your partner to be everything.

[Michelle Obama]

That's right.

[Craig Robinson]

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

[Tracy Ellis Ross]

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

[Craig Robinson]

I'll say, but it's not sticking.

[Tracy Ellis Ross]

Yeah, but that could be timing, right?

[Michelle Obama]

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

[Tracy Ellis Ross]

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

[Michelle Obama]

It's in my opinion. You don't have to know. We just have our deeply held opinions about Ronan's life.

[Tracy Ellis Ross]

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

[Michelle Obama]

Yeah, okay.

[Tracy Ellis Ross]

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.

[Craig Robinson]

I agree with you not agreeing with me.

[Tracy Ellis Ross]

You know what I mean? Like, I'm just like, no, I don't. That's. No. I am 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 if you're doing all the right things. Do 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.

[Michelle Obama]

Out of the hallway?

[Tracy Ellis Ross]

You know, when you find a room. 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.

[Michelle Obama]

Yeah.

[Tracy Ellis Ross]

And so I'm gonna.

[Craig Robinson]

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

[Michelle Obama]

See, I thought. I'm all like, that's true. Craig's like that. It's Mr. Nice Guy.

[Tracy Ellis Ross]

I didn't hear from him for a while.

[Craig Robinson]

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

[Tracy Ellis Ross]

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.

[Michelle Obama]

That's right.

[Tracy Ellis Ross]

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.

[Michelle 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, encourage him to 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 in long term relationships, you're gonna have deep, deep dips and you're gonna have.

[Tracy Ellis Ross]

You're gonna have a bad year.

[Michelle Obama]

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. You know, I mean, I've been married to my husband for 30 plus years. I mean, the truth is, if you. 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.

[Craig Robinson]

You'd sign up for it.

[Michelle Obama]

You'd sign up for it.

[Craig Robinson]

You'd sign up for it.

[Michelle Obama]

You know, and that's really how it works out.

[Tracy Ellis Ross]

That's the reality.

[Michelle Obama]

But the reality is, is that if you choose to have a traditional marriage and you have kids, let me tell you, the years of 1 to 13 will be bad for you as an adult, you know, because it's beautiful. But they'll. Yeah, they'll take you for a loop. And you love them and you don't want to hate them because they're cute. So you're going to be mad at the person who is sitting next to you, the other adult, the one who.

[Tracy Ellis Ross]

Helped you make it.

[Michelle Obama]

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 match that we're all. Those 30 years are going to be blissful.

[Tracy Ellis Ross]

Yeah. Well, that's crazy.

[Michelle Obama]

And it's like, that's just not going to happen.

[Tracy Ellis Ross]

Can I just ask what some of the 32 things on the list were of the questions?

[Craig Robinson]

Yes.

[Tracy Ellis Ross]

I'm curious.

[Craig Robinson]

Yes.

[Tracy Ellis Ross]

Is that okay? Is that okay? Is that valid?

[Michelle Obama]

Is that valid question?

[Tracy Ellis Ross]

You're okay to answer that.

[Michelle Obama]

That is so good. It is good. It is good.

[Tracy Ellis Ross]

It might help Ronan.

[Craig Robinson]

It might help Ronan and me.

[Michelle Obama]

I'm trying to remember what they were. What was item 30.

[Craig Robinson]

So I guarantee you Kelly still has the list.

[Tracy Ellis Ross]

Oh, that's fantastic.

[Michelle Obama]

You should get her on the phone.

[Craig Robinson]

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?

[Michelle Obama]

Troy. Say that again.

[Craig Robinson]

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 we're going somewhere and the same with you. We go into a room, we might not be right next to each other.

[Michelle Obama]

We're not gonna be couple to couple.

[Craig Robinson]

We're not gonna be couple to couple. Are you okay with me standing alone? Cause I could stand alone. I was like, oh, okay.

[Tracy Ellis Ross]

I love that question.

[Michelle Obama]

So that was her question to you or your question to her?

[Craig Robinson]

That was one of her questions to me.

[Tracy Ellis Ross]

That's a great question.

[Craig Robinson]

That was the one. That was not a category.

[Tracy Ellis Ross]

I'm gonna throw that at one of.

[Michelle Obama]

The people I'm dating.

[Craig Robinson]

Yes.

[Michelle Obama]

Look out, mister, Whoever you are.

[Craig Robinson]

And I stand alone. That's so important to me, especially the way my family is for you to be able to stand alone.

[Michelle Obama]

So that's a great one.

[Craig Robinson]

And then there were sort of.

[Michelle Obama]

That's a really good one.

[Tracy Ellis Ross]

I love that question.

[Craig Robinson]

And then the one that we spent the most time on were, what are your deal breakers? 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.

[Michelle Obama]

Yeah.

[Tracy Ellis Ross]

That's really smart.

[Craig Robinson]

Yeah. Yeah. And. And I will tell you, this was.

[Michelle Obama]

A. 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?

[Tracy Ellis Ross]

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

[Michelle Obama]

Right.

[Tracy Ellis Ross]

That's just the thing. I would ask that.

[Michelle Obama]

Are you secure, Trifling.

[Tracy Ellis Ross]

That is exactly right.

[Michelle Obama]

Are you so insecure. Yeah. That you can't.

[Tracy Ellis Ross]

Are you uncomfortable with my bigness?

[Michelle Obama]

That's right. You know, and then don't ask it. All right. That's.

[Tracy Ellis Ross]

He would be so.

[Craig Robinson]

Cause I am a boss. I am a boss.

[Tracy Ellis Ross]

I'm a boss. Are you okay being that?

[Michelle Obama]

Can you level up? Can you level up? And then he's running away going.

[Tracy Ellis Ross]

He's aggressive. Yeah. That was really helpful.

[Michelle Obama]

That's a good way to think about it.

[Craig 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?

[Tracy Ellis Ross]

Well, I Think it depends because I don't think we have enough information from Ronan. Right. 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? 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?

[Michelle 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 laugh, 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. Dating, you know, there's no guy.

[Tracy Ellis Ross]

Did he call again? Exactly.

[Michelle Obama]

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

[Tracy Ellis Ross]

Yes, he can.

[Michelle Obama]

He can date and can and. But be more reflective about the process. And I think that's true for everyone. If you want to have a partner, you got to know yourself.

[Tracy Ellis Ross]

Yep.

[Michelle Obama]

It's dating and having an internal conversation. Agreed about why you're wise, 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 don't know if I want to be like them, you know, love them, love their marriage. But I didn't date for. I want to do what my mom and dad did. And I think, Craig, you were more that kind of. This is the way it works.

[Craig Robinson]

It was 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. I was following a strategy, and that's just not. I don't want Ronan to do that.

[Michelle Obama]

I don't want any young. I want this generation of young people to be more thoughtful.

[Tracy Ellis Ross]

Yeah, 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 the 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 do like to ask people is, how do you argue?

[Michelle Obama]

Oh, that's a good one.

[Craig Robinson]

Yeah, that was on the list. Yeah, that was on the list.

[Michelle Obama]

That was 12.

[Craig Robinson]

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

[Tracy Ellis Ross]

That's a good one. You know, my siblings, we all. There's a way that my family argues that I'm comfortable with, and I've been. Cause I get loud and then it's done. Like, I'm so straightforward. I'm not somebody who's gonna, like, hold it. Like I'm gonna say it. For some people, that's terrifying.

[Michelle Obama]

Yes, yes, yes.

[Tracy Ellis Ross]

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. Yeah.

[Michelle 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.

[Tracy Ellis Ross]

Yeah, it's.

[Michelle Obama]

And it's. And it is reasonably hard. You know, it's.

[Tracy Ellis Ross]

It's the right kind of hard.

[Michelle Obama]

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

[Tracy Ellis Ross]

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

[Michelle Obama]

That's right.

[Tracy Ellis Ross]

And if you want anything out of it, it's gonna be work, you know, and relationships included. I. 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?

[Michelle Obama]

That's right.

[Tracy Ellis Ross]

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?

[Michelle Obama]

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

[Tracy Ellis Ross]

Yeah.

[Michelle Obama]

Because sometimes, maybe for men or if they can be choosers or people in general, they think something. There's something wrong in the dating process, and it's like, nah, it's just what it means to be with somebody else. It's complicated. It's hard. It requires compromise. It requires you to change and adapt all throughout the process. 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.

[Craig Robinson]

Exactly.

[Michelle Obama]

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

[Tracy Ellis Ross]

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

[Michelle 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.

[Tracy Ellis Ross]

Do you have the 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?

[Craig 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 that's what I.

[Tracy Ellis Ross]

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

[Craig Robinson]

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

[Michelle Obama]

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

[Craig Robinson]

Perfect time to give Ronan some takeaways.

[Tracy Ellis Ross]

Okay.

[Michelle Obama]

Okay.

[Craig Robinson]

And I'm gonna.

[Michelle Obama]

You're the master.

[Tracy Ellis Ross]

You took notes. You take away.

[Michelle Obama]

Come on, coach.

[Craig Robinson]

Do it. Tell us. The self reflection has to be at the top.

[Michelle Obama]

Yes.

[Craig Robinson]

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

[Tracy Ellis Ross]

Chemistry and love.

[Craig Robinson]

Yeah, Chemistry and love. Or is this just the I'm not in love with you kind of thing?

[Tracy Ellis Ross]

What's important to him in a relationship?

[Craig Robinson]

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

[Tracy Ellis Ross]

And. Can I reframe that?

[Craig Robinson]

Yes, you can reframe that.

[Tracy Ellis Ross]

Just call it the work. Cause it's not extra work. That's just the work it takes.

[Craig Robinson]

Okay, yeah, do the work. Do the work.

[Michelle Obama]

And I have one last thing. 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. 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. That's what I'm raising them to be, is like, how are you happy with how life 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, live, grow, adapt for your own.

[Tracy Ellis Ross]

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 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? Well, Tracy, what a fun conversation.

[Michelle Obama]

I love you.

[Tracy Ellis Ross]

I love you right back.

[Michelle Obama]

Yeah.

[Tracy Ellis Ross]

This was so nice of you.

[Craig Robinson]

This was so nice. Thank you for doing this.

[Michelle Obama]

Yeah. Yeah. And, you know, your vulnerability, your willingness to share, be open, always refreshing.

[Natalie]

Thanks.

[Michelle Obama]

So. See ya.

[Tracy Ellis Ross]

That's my currency.

[Michelle Obama]

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

[Craig Robinson]

Thanks.

[Tracy Ellis Ross]

I will.