Break Up With Him When It’s Over with Elaine Welteroth

Summary

Podcast Summary: "Break Up With Him When It’s Over with Elaine Welteroth"

Podcast Information:

• Title: IMO with Michelle Obama and Craig Robinson
• Host/Author: Higher Ground
• Episode: Break Up With Him When It’s Over with Elaine Welteroth
• Release Date: April 9, 2025

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Introduction

In the enlightening episode titled "Break Up With Him When It’s Over," Michelle Obama and Elaine Welteroth delve into the complexities of relationships, particularly focusing on the importance of aligning life goals and the courage to make difficult decisions when those goals diverge. This episode provides listeners with heartfelt advice, personal anecdotes, and empowering insights aimed at navigating the often challenging terrain of romantic relationships.

Listener Question: Aligning Life Goals in Relationships

The episode centers around a poignant question from a listener named Alice:

Alice: "I’m 30 years old and have been in a relationship for six years. I desperately want to have children, but my boyfriend doesn’t feel ready and doesn’t think he will ever want kids. We’re very much in love and see a future together, but I can’t imagine life without children. Have you ever seen a man change his mind about wanting kids in his 30s? If so, what prompted it? And if we break up, what important questions should I ask potential suitors to avoid misalignment in the future?"
(Timestamp: 02:40)

Michelle Obama’s Personal Story

Michelle Obama shares a deeply personal story from her past, drawing parallels to Alice’s situation:

Michelle Obama: "When I was 25, I found myself in love with a 50-year-old man who already had children. At that time, I wasn’t thinking about having children, and we were having a great time. However, as the relationship deepened, it became clear that he didn’t want kids. I realized that despite my hope that circumstances might change, I needed to honor my true desire for motherhood.
(Timestamp: 05:01)

Michelle emphasizes the vital lesson taught by Maya Angelou:

Michelle Obama: "When somebody shows you who they are, believe them. If someone tells you they don’t want children and that’s something you deeply desire, you have to acknowledge that and make decisions accordingly."
(Timestamp: 06:19)

Lessons Learned and Advice

Michelle reflects on the importance of self-awareness and the courage to make tough choices:

Michelle Obama: "I decided to leave that relationship to allow for the possibility of finding a partner who shares my vision. Looking back, I'm grateful I didn’t try to change someone against their will. It was a crossroads where I chose to prioritize my dreams and values."
(Timestamp: 08:02)

She further advises Alice and listeners on the significance of patience and self-love:

Michelle Obama: "Sometimes the prayers that go unanswered are the ones you will be most grateful for later. It’s about falling in love with yourself first and ensuring that any partnership you enter into complements your life and aspirations."
(Timestamp: 36:30)

Elaine Welteroth’s Perspectives

Elaine Welteroth adds her insights, reinforcing the importance of clarity and self-worth in relationships:

Elaine Welteroth: "We’re often raised to follow a certain path—marriage, kids, in that order. But life is unpredictable, and your value isn’t defined by ticking societal boxes. I advise my mentees to embrace their individuality and not feel incomplete without conforming to traditional expectations."
(Timestamp: 10:00)

She highlights the necessity of open communication:

Elaine Welteroth: "Don’t be afraid to ask the hard questions early on. Clarity is not desperation—it’s about understanding your partner’s intentions and ensuring alignment in your life goals."
(Timestamp: 34:35)

Choosing the Right Partner

The conversation transitions to the process of selecting a life partner who aligns with one’s values and goals:

Michelle Obama: "Choosing a partner is like assembling a team. Each person needs to bring different strengths and be willing to support each other through life’s unpredictable challenges. It’s essential to find someone who is committed to honest communication and shared values."
(Timestamp: 46:07)

Elaine emphasizes the importance of partnership and mutual support:

Elaine Welteroth: "Life throws unexpected challenges, especially when raising children. It’s crucial to be with someone who is an equal partner—someone who can handle various responsibilities and support you through thick and thin."
(Timestamp: 47:05)

Empowering Women to Prioritize Their Goals

Michelle and Elaine discuss the societal pressures women face regarding age and life milestones:

Michelle Obama: "There’s a pervasive narrative that women have an expiration date on their desirability, especially as they age. But your value isn’t tied to this. Prioritize what you truly want, whether it's motherhood or personal fulfillment, and free yourself from societal constraints."
(Timestamp: 35:15)

Elaine echoes this sentiment, encouraging women to seek clarity and self-empowerment:

Elaine Welteroth: "Don’t wait for life to come to you. Actively pursue your dreams and make informed choices in your relationships. It’s okay to prioritize your happiness and long-term goals over temporary comfort."
(Timestamp: 43:09)

Parenting and Teaching the Next Generation

The discussion shifts to Elaine’s role as a mother and how she imparts these lessons to her daughters:

Elaine Welteroth: "I strive to create an open environment where my daughters feel empowered to voice their desires and make informed decisions. By sharing my experiences—both successes and mistakes—I hope they build healthy, fulfilling relationships based on mutual respect and shared values."
(Timestamp: 49:36)

Michelle adds her perspective on the influence of parental guidance:

Michelle Obama: "I wouldn’t be the mom I am without my own mother’s wisdom. It’s essential to guide our children while allowing them the space to learn and grow from their own experiences."
(Timestamp: 52:29)

Closing Thoughts

In their concluding remarks, Michelle and Elaine reinforce the episode’s core message: the importance of self-love, clear communication, and aligning life goals in relationships. They encourage listeners to embrace their journeys, make empowered decisions, and prioritize their true desires over societal expectations.

Michelle Obama: "Make the best decisions for your life based on what you can see right now. Trust that the future holds beautiful possibilities, even if the path isn’t entirely clear."
(Timestamp: 54:11)

Elaine Welteroth: "Find out what you need to know in your relationships. If your partner can’t handle honest conversations about your future, that’s a sign that the relationship may not be right for you."
(Timestamp: 56:27)

Key Takeaways

• Self-Awareness: Understanding and prioritizing your life goals is crucial in any relationship.
• Clear Communication: Honest dialogues about future aspirations prevent misalignment and potential heartbreak.
• Empowerment: Embrace your individuality and resist societal pressures that dictate your life’s trajectory.
• Selective Partnership: Choose partners who share your values and are committed to mutual support and growth.
• Parental Guidance: Share experiences and lessons with the next generation to foster healthy relationships.

This episode serves as a heartfelt guide for anyone grappling with relationship dilemmas, emphasizing the importance of staying true to oneself and making empowered choices for a fulfilling life.

Transcript

[Michelle Obama]

So this is. I've never told anyone this, Mrs. Obama, but I'm going to tell you this because it applies to this person's situation. When I was 25, I happened to be dating. Don't judge me, Mrs. Obama.

[Elaine Welteroth]

Okay, let's hear it. Okay.

[Michelle Obama]

You promise?

[Elaine Welteroth]

I don't know. I can't promise right now. It's a safe space. It's a space.

[Michelle Obama]

You have two daughters. I'm sure they brought you some.

[Elaine Welteroth]

Some. Some stuff. Please.

[Michelle Obama]

And you've had to keep them.

[Elaine Welteroth]

And some things I've had to say. Don't tell your father that. O. This episode is brought to you by Pine Sol and Theraflu. Well, hey. Hey. I am here. We are here chatting. I'm solo this time. I usually have my big brother Craig, to join me in these conversations, but he's feeling under the weather. But we're gonna proceed without him because we've got a great question that is perfect. Perfect for our guest. And I want to welcome one of my favorite people, Elaine Walter Roth, who, you know, goes without any introduction. She is beautiful, smart, sharp, awesome. Her resume. She's a New York Times bestselling author, award winning journalist, former judge on one of my favorite shows that I still never got to go and sit and judge.

[Michelle Obama]

It could still happen.

[Elaine Welteroth]

Project Runway. We'll see. It's on my bucket list. Another thing that you are known for is being at the helm of Teen Vogue, doing great things. But you've also launched Birth Fund, which is a foundation that provides grants for midwifery, birth support, and holistic prenatal care for mothers. And I didn't know about that work. You're doing it all.

[Michelle Obama]

Look who's talking.

[Elaine Welteroth]

Thanks for being here, Elaine. We've got a great question that's right up your alley. But before we jump in, I just want to check. How you doing? You look great.

[Michelle Obama]

Feeling great.

[Elaine Welteroth]

You got some things going on.

[Michelle Obama]

Some things.

[Elaine Welteroth]

Some things tell us all about.

[Michelle Obama]

Some big things are popping, literally, about you. Well, first of all, thank you so much for having me. What a dream. I am 33 weeks pregnant. 32, I think. 32 weeks pregnant today.

[Elaine Welteroth]

Congratulations.

[Michelle Obama]

Thank you so much. This is the perfect way to bless the bump before we get into that final, final stretch.

[Elaine Welteroth]

But. But it's a good segue into. Well, it's almost a good segue because it's like, before you get to having the baby, you gotta choose who you're.

[Michelle Obama]

Gonna do it with.

[Elaine Welteroth]

Gotta figure out who you're gonna have it with. And that takes us to our question for Today from a young woman named Alice who's 30 years old and is trying to figure out this whole mothering thing.

[Alice]

Hi, Michelle. My name is Alice. I'm 30 years old and I've been in a relationship for about six years. I desperately want to have children and I know that I want to be a mom. However, my boyfriend doesn't feel ready and doesn't think he will ever want kids, but he's not totally sure. We are very much in love and do see a future together, but I just can't imagine a life without children. And I feel like I need to know soon whether or not that's in the cards for us. So I can move on if I need to. So my question is, have you ever seen a man change his mind about wanting kids in his 30s? And if so, what prompted it? And if we do decide to break up and I reenter the dating scene, what important questions should I be asking potential suitors to avoid spending another six years in a relationship where our visions are not aligned? Thank you.

[Elaine Welteroth]

So, yeah. This speaks to you.

[Michelle Obama]

Doesn't speaks to 25 year old me.

[Elaine Welteroth]

It does, really. So these were. Yeah. And I get these kind of questions from my young staff, my mentees, you know, at that age. And a lot of women are struggling with the. Finding a mate, finding a good mate, dealing with the biological time clock. Thinking about freezing eggs. Just. It feels more fraught than it maybe even was for me when I was that age. But I want to hear a bit of your journey around this, this question.

[Michelle Obama]

So this is. I've never told anyone this, Mrs. Obama, but I'm gonna tell you this because it applies to this person's situation. When I was 25, I happened to be dating. Don't judge me, Mrs. Obama.

[Elaine Welteroth]

Okay, let's hear it. Okay.

[Michelle Obama]

You promise?

[Elaine Welteroth]

I don't know. I can't promise right now. It's a safe space. It's a space.

[Michelle Obama]

You have two daughters. I'm sure they brought you some stuff.

[Elaine Welteroth]

Please.

[Michelle Obama]

And you've had to keep them.

[Elaine Welteroth]

And some things I've had to say. Don't tell your father that. Okay? Just keep that between us.

[Michelle Obama]

Let's just say this is one of those things.

[Elaine Welteroth]

Okay.

[Michelle Obama]

This is one of those things. So when I was 25, I found myself in love with a 50 year old man.

[Elaine Welteroth]

Okay. All right.

[Michelle Obama]

And this 50 year old man already had children. And at the time, you know, I weirdly wasn't thinking about children.

[Elaine Welteroth]

Yeah.

[Michelle Obama]

And we were having a great time, you know, really wasn't worried about the future. But the deeper we got into the relationship, it came up that he didn't want to have children.

[Elaine Welteroth]

How long were you dating before you.

[Michelle Obama]

It came up pretty, pretty early on, I would say. And when he said he didn't want to have kids, I kind of heard what she heard, which is like, well.

[Elaine Welteroth]

Maybe there's still a chance, right?

[Michelle Obama]

You know, I think when we're young, we think that we can maybe change people and we think that maybe we could inspire a change. Right? Like love conquers all and love. But, you know, there are some practicalities in life that you do have to consider. And one of the most important things that my mom has ever told me that Maya Angelou has said, is that when somebody shows you who they are, believe them. Or in this case, tells you who they are, believe them the first time.

[Elaine Welteroth]

That's right.

[Michelle Obama]

And this applies in this situation. If this man has said to you, I love you, but I don't want to have kids. And if you know deep down that that is something you really, really want, you have to.

[Elaine Welteroth]

You gotta know that and keep it moving.

[Michelle Obama]

You gotta. Unfortunately, you might have to wrap things up.

[Elaine Welteroth]

How long were you in the relationship before you kind of thought a year. Okay, well, see, that's. Yeah. Truthfully, at 25 or 30, you know, young women are still figuring themselves out, you know, and just to cut you a little bit of Slack, at 25, please. You were a baby, you know, and you were still figuring out who you were. And in our 20s, we are more malleable, you know, we're more open to possibilities. And you're with an older man who makes you feel mature and you feel secure in it. I mean, my question is not to you at 25, but it's to him at 50.

[Michelle Obama]

I have the same question. Now, looking back, as a 37 year.

[Elaine Welteroth]

Old woman, I have the same question right now. I mean, because first of all, it's like a 50 year old man is dating a child. And that may feel fun and easy, right. In so many ways. But my question to him is, why are you wasting her time? And, you know, you don't want to have kids, you know, so some of the burden is on the guy. He's already been married, has had his kids, you know, so it takes two. And at 25, you learned an important lesson.

[Michelle Obama]

I want to tell Alice that sometimes the prayers that go unanswered are the ones you will be the most grateful for down the line. Because I will tell you now, looking back, thank you, Jesus, that I did not end up Going down that path and hoping that this man would change his mind. And, you know, God forbid he did. One of the things he would say, and I gotta give him credit, he did say, I do not want you to look up in your 30s and go, I gave the best years of my life to this guy when we don't want the same things going into the future. And he said he would say, you know, having kids is a young man's game. And at 25, I didn't get that. At 37, going on two kids with an energetic young man who was my age, who can keep up with me. Oh, I get it now.

[Elaine Welteroth]

That's right.

[Michelle Obama]

It is something that you have to have the conviction. And I think that, you know, in relationships, yes, you have to make compromises.

[Elaine Welteroth]

Yeah.

[Michelle Obama]

And, yes, you will. You'll hear that a lot from married couples, but there are some things you do not compromise on, and kids is one of them. If you do not have the conviction, if you don't really, really desire that, you are better off not wasting another person's time and entering into that lifelong partnership. Because if you can't support her fully in motherhood, leave her alone.

[Elaine Welteroth]

There are many ways to live a full life, and we're raised as young women to think it's marriage, it's kids, in that order. And that's one thing we don't have control over. You know, you don't know if you're gonna fall in love. You don't know if you're gonna have find the right person. You don't know how life is gonna unfold. Ain't that the truth? And I find that I know some of my young mentees feel less than because they haven't found somebody or they haven't had a child. And it breaks my heart because these are beautiful, smart women who have amazing lives. But because one piece of the puzzle isn't there, a piece that they've been told their whole lives they should want and have. It's almost like life has no purpose. And one of the things I want, my daughters, I'm trying to deprogram them from that belief that there's a certain way to be a woman in this world. Because I don't know what their future is going to hold. So I don't talk about when you become a mother or when you get married. I say, well, if you find somebody, if you choose that, if that's something you want for yourself, but understand that you can have a beautiful life without all that. Absolutely, you know, you are not less of a person because somebody didn't choose you or you didn't find somebody.

[Unknown]

This episode is brought to you by theraflu. We've partnered with theraflu to spread awareness about the amazing work they're doing to fight for paid sick days for all workers in America. Mish, don't you remember when dad didn't feel comfortable taking paid sick days?

[Elaine Welteroth]

Well, I didn't realize he didn't feel comfortable. And just to remind folks, our dad was a blue collar worker. He worked as a stationary fireman for the water filtration plant for the city of Chicago. So he was a shift worker. But I do. What I remember is that our dad never. I can't remember him ever taking a sick day or a day off other than his signed vacation days, never. And I didn't know why. I just thought, you know, he just had a great work ethic, which I think he did.

[Unknown]

Which he did. But he never, it seemed like he was either never sick, which we know now was impossible.

[Elaine Welteroth]

First of all, our father had multiple sclerosis. So I would imagine there were days that he woke up and he probably felt tired. He probably felt a level of exhaustion that came with the disease, but he just pushed through.

[Unknown]

He just really just fought through it and didn't want to take any sick days.

[Elaine Welteroth]

And like too many folks in this country.

[Unknown]

Right?

[Elaine Welteroth]

Yeah.

[Unknown]

Right, Right. Theraflu firmly believes that the ability to rest and recover when sick should be a right, not a privilege. And I love that. Theraflu's Right to Rest and Recover campaign was created to help offset the financial burden that Americans without paid sick leave feel when they take a sick day. So far, seven and a half million workers have been impacted by this initiative, and Theraflu is committed to keeping the fight going because no one should have to work sick or choose between their health and their job. Learn more or help someone apply for the [e-mail] righttorecover we are so thrilled that Pine Sol is a partner of imo. Pine Sol has been connected to our family forever. To this day, whenever my sister and I catch the scent of Pine Sol, we automatically feel better about life. The smell of Pine Sol has always taken us back to our childhood home. It is amazing how smells can transport you to a place or a moment in time. Another smell that takes me back is cherry blossoms, which always remind me of visiting Michelle in D.C. that's why I'm excited for Pine Sol's newest scent, Cherry Blossom. The cleaning power you know and love from Pine Sol is available In a new scent this spring, Cherry Blossom, which is light and fresh and leaves a lasting floral scent while eliminating tough dirt, grease and grime. You can use Pine Sol Cherry Blossom Multi Surface Cleaner to help deodorize and clean hard non porous surfaces, including floors, sinks, counters, stoves, bathtubs, shower stalls, tile and more. Visit pinesol.com to find where to shop Pine Sol Multi Surface Cleaner in the new fresh Cherry Blossom scent.

[Elaine Welteroth]

Yes, and especially for black women. You know, I mean, we can talk about how hard it is to be chosen in this day and age.

[Michelle Obama]

I love to talk about being the choosers, though.

[Elaine Welteroth]

I know.

[Michelle Obama]

I love.

[Elaine Welteroth]

I do. Well, let's talk about that. Well, I think.

[Michelle Obama]

I do think there's this. This narrative that you have to wait to be chosen and what it means to be chosen by a man. And I think I had that. I call it the Carrie Bradshaw complex. You know, growing up with Sex and the City as the kind of the.

[Elaine Welteroth]

Waiting for Mr. Big to show up.

[Michelle Obama]

And that was my Mr. Big.

[Elaine Welteroth]

That was my black Mr. Big.

[Michelle Obama]

And I'm so glad that in that stage of life, God did not give me what I thought I wanted and needed because what I got was what I truly deserve. And I'll tell you, that breakup was the hardest breakup because it represented this.

[Elaine Welteroth]

Like, the breakup with the old guy.

[Michelle Obama]

The breakup with the older guy that I thought I wanted to do it all with was one of the hardest breakups for me because it was the disillusion of this constructed, concocted dream that had been fed to me that I embraced as, like, the only way to do it.

[Elaine Welteroth]

That's what I'm.

[Michelle Obama]

Yeah, right. And it was like this idea that some man is gonna come along and save me and choose me and give me this life. You go to New York, you live your big, fabulous life, and then you gotta find the guy with the, you know, the money bags, the guy with all the things going on. If you think. If you really stop, you're like, wait a minute. And we call ourselves feminists.

[Elaine Welteroth]

Yeah, that's right.

[Michelle Obama]

And we're subscribing to this notion.

[Elaine Welteroth]

Yes.

[Michelle Obama]

So it took a lot of unlearning for me to realize that, hold on a minute. I can be that rich, successful man that I was told to marry.

[Elaine Welteroth]

Yeah, great. I can be that one.

[Michelle Obama]

And I can choose the kind of partner that is going to compliment my life, my dreams and what I want and vice versa.

[Elaine Welteroth]

What flipped that switch for you? Was it the breakup, Jonathan?

[Michelle Obama]

The breakup was the humbling, but also, I wouldn't just say humbling. It was a moment of empowerment because I decided to leave that relationship.

[Elaine Welteroth]

So what's from feeling defeated in that moment? Because a lot of people, a lot of women will experience a breakup from Mr. Big and they'll think it's me. Because taking that power back in relationships and dating, a lot of us don't do that. So what do you think got you to a better place?

[Michelle Obama]

It wasn't my first time at the rodeo. I had had a couple of relationships before that that taught me this really important lesson. And I remember this is something that Oprah said. You walk at the whisper before it becomes a roar. I had not done that in the relationship prior to dating this older man. And I thought, the one thing I know for sure is that I will never wait for the roar again. And so one of the contracts that we made when we first came together, because at the. Just so you know, just so you know, Mrs. Obama, I did not know the man's age when we started dating, and he didn't know my age.

[Elaine Welteroth]

I'm not feeling him. This guy, I know you. You're like my mama.

[Michelle Obama]

You're like my mama. My mom, my mom told me this summer, finally told me. She said that was one of the hardest times in my life as a mother.

[Elaine Welteroth]

It was hard for her to watch you go through that.

[Michelle Obama]

And I was like, mom, you acted like you were fine with it. She was like, that was an act.

[Elaine Welteroth]

That's exactly what that was. And if she had said something, you would have dated him for another two years.

[Michelle Obama]

That's what she said.

[Elaine Welteroth]

That was the, that was her expertise at work there. You guys were talking, you know, I could feel it. You could feel it. I can feel it because I don't even know the dude and I'm mad at him.

[Michelle Obama]

Well, he's out of the picture. Okay, ladies, but just so we all are clear here, I did not know his age. He didn't know my age until we were further down the line. So we made a pact with each other and we said, he said, actually, can you let me know if you're ever not having fun? If you're not happy anymore, will you let me be the first to know? And that coupled with this idea that Oprah, Mrs. Oprah Winfrey has planted in my mind, it allowed me to do these self check ins. And the deeper we got into the relationship and the more that I recognized that while I may not want to have a kid today, I can't really envision my life without the experience of Becoming a mom. And when I do that, I want an enthusiastic partner in that. And you don't want somebody.

[Elaine Welteroth]

You don't want to.

[Michelle Obama]

I don't want to drag somebody, pull.

[Elaine Welteroth]

Somebody kicking and screaming into parenthood.

[Michelle Obama]

I didn't want that for myself. And so I thought, you know, this is one of those decisions. I am at a crossroads. I can either take what he's willing to give me, or I can cut him loose and allow for the possibility to get what I deserve.

[Elaine Welteroth]

Good for you.

[Michelle Obama]

And so I packed up my clothes and I left.

[Elaine Welteroth]

And you were living with them, too?

[Michelle Obama]

I wasn't living. I was just staying over there a lot. Mrs. Obama had my own apartment.

[Unknown]

Okay.

[Michelle Obama]

I was an independent woman.

[Elaine Welteroth]

I was like, no, no.

[Michelle Obama]

I was climbing in my career, by the way. I did not slow down in my career for this relationship. I kept climbing. And, you know, so I'm very proud of myself for that. I kept on my path, but I decided to leave that relationship to allow for the possibility that it gets better. And do you know that I reunited with Jonathan, this kid from church.

[Elaine Welteroth]

The church boy.

[Michelle Obama]

The church boy.

[Elaine Welteroth]

The good old church boy. The good old church boy that you overlooked. They looked right past Jonathan. I sure did. I sure did.

[Michelle Obama]

Mrs. Obama. And now we met up. He happened to be in town. We met up. And I just remember being like, when.

[Elaine Welteroth]

Did he grow up? Really? Jonathan. Wow. I have always tried to tell, you know, you can't tell your kids anything. But there have been some guys in my daughter's lives that I've been like, don't sleep on him.

[Michelle Obama]

You know, that was like, the nice ones.

[Elaine Welteroth]

The nice ones, right? What is it about the nice ones that there's an age where you just want something bad, Right. You just want something all wrong.

[Michelle Obama]

What is that? I had that. I had that syndrome. But we gotta go on our own journeys. And, you know, I will say I'm so grateful for all the frogs. A kissed before meeting what truly is my version, not to be cliche and.

[Elaine Welteroth]

Cheesy, but my version, my real Mr.

[Michelle Obama]

Big, my real Prince Charming. And I will tell you right away, I felt at home.

[Elaine Welteroth]

Yeah.

[Michelle Obama]

I felt my nervous system was calm. It was the opposite of what I felt in these other relationships where it was like, my heart is pounding. It wasn't that. It was this piece.

[Elaine Welteroth]

Say that again. No. For the people in the back. For the people in the back, because. Well, to share my experience. Meeting Barack. Right?

[Michelle Obama]

Yeah.

[Elaine Welteroth]

I want to hear this story. There was frog kissing. And to anybody out there. No, you're Not a frog, but not the right person.

[Michelle Obama]

Right.

[Elaine Welteroth]

But when I met Barack, and I also think that dating is important because you've got to try on some things to know what really fits. Because you might not have been able to appreciate Jonathan had you not dated Mr. Big.

[Michelle Obama]

That part.

[Elaine Welteroth]

So I dated some Biggs.

[Michelle Obama]

You had some Mr. Biggs.

[Elaine Welteroth]

Not old rich people, but the version of the person who just wasn't right. And I knew they weren't right, but because I had those experiences when Barack showed up and there was, as you describe it, this sort of calm. Right. There wasn't this. There was just complete and total honesty and trust. This was a man who knew what he wanted. So there was none of the guessing games that I think we as women get used to playing and kind of enjoy it.

[Michelle Obama]

Yes.

[Elaine Welteroth]

Being with somebody where it's a total. I don't know if he likes me and maybe he'll call. And, you know, we kind of sometimes get into that game and we mistake that game for love, but it's a game, and it's an uncomfortable game if we're honest with ourselves. Does he really like me? Did he call? I don't know what that meant. Nothing is straightforward. Everything is ambiguous. And I met somebody who was unambiguous and clear. And that feeling was new, but it was the right feeling to look for. You know, you shouldn't have to wonder about your goals and visions with the person that's right for you. You should be able to have real clear conversations up front and say, this is who I am. Take it or leave it. Who are you? You know, do you believe in marriage? Do you want kids? Let's not play a guessing game. And I try to advise young women in my life not to play games in dating. Ask the questions you need to know and don't be embarrassed by it. Barack was that comfort zone for me. And it was very clear, very early that he was different. And different is good. You know, different is not about games. Because I didn't want to. To deal with somebody that I couldn't talk to, that I couldn't trust, that I didn't know what he thought. That wasn't a good communicator. And sometimes we look right over those people who are in front of us because we're drawn to the game.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

Woo. You're preaching. Yeah. Yeah.

[Michelle Obama]

So did you two speak about these things early on in your dating life? Did you ask, do you want kids? Did you ask, do you wanna be married?

[Elaine Welteroth]

Yeah. Yeah. And actually, Barack, when we first started dating, Would, you know, he was like, well, I'm not really sure if I believe in the institution of marriage.

[Michelle Obama]

Oh, he was one of those.

[Elaine Welteroth]

Yeah. And I was sort of like, really? You know, what's that for? And I didn't, you know, it wasn't consistent with, you know, who he was. But he would poke at that, Right?

[Michelle Obama]

Yeah.

[Elaine Welteroth]

But he was also the person who asked me out who said we should date. I was very hesitant about dating because we worked at the same law firm. I was a year. He's older than me, but I went to law school and was practicing. Like, he hates for me to say I was his mentor.

[Michelle Obama]

I was gonna say, say it. You were his boss.

[Elaine Welteroth]

I wasn't his boss because I wasn't senior enough to give him assignments. But I was sort of helping him adjust. And I sort of thought, well, I shouldn't date the guy that I was assigned to help. Right. I thought that'd be tacky, especially we were two of a few black people in the firm. We both went to Harvard. It just felt a little cliche. And I didn't wanna be that associate. Right, Right. But he was like, who cares? We got to know each other for the first month of the summer. And he was like, you're cute, you're smart, you're funny. Let's go on a date, you know? I was like, no, we shouldn't go on a date. That doesn't seem right.

[Michelle Obama]

But he was like, he knew what he wanted.

[Elaine Welteroth]

He knew what he wanted. Right. And he wasn't worried about the job or appearances. He was like, this makes sense to me. And you don't get that a lot. It's romantic, you know, or. I know I didn't get that a lot from guys. You. You.

[Michelle Obama]

No, same.

[Elaine Welteroth]

I mean, you're guessing for the first few months. And I was like, well, why am I drawn to that and not drawn to the truth? Right. So I chose the truth with Barack. I chose to be with somebody who came to me on clear terms. And so as a result, that's how our relationship started. We were already friends, so we could have these conversations. And I knew he didn't mean the thing about marriage, but his proposal, which I didn't know was coming, goaded me into this argument about marriage. So Barack had studied and taken the bar, and we had been dating for all through his law school year. So it was about two years. So he took me out to a nice dinner, our favorite fancy restaurant in Chicago, under the guise of celebrating that he finished the bar. Um, little did I Know that he had asked. My parents had gotten a ring. And so we're sitting at dinner, I'm thinking that it's a regular date. Midway through the entree, he starts talking about not believing in marriage again. And I was like, don't tell me that's how he went into his proposal. No, no. So he was winding me up. And of course, I, you know, I was just not feeling it. So I just went off on him. And I was like, this isn't gonna last. And if you don't believe in marriage, don't waste. And, you know, and I don't understand. And I wouldn't have kids out of wedlock. You know, we had had this conversation, but he was just winding me up, you know, And I think I was being wound up all through the entree.

[Michelle Obama]

What a way to get to her.

[Elaine Welteroth]

And then we. Then. And he was. He was not arguing back. He was just sitting there with his finger on his temple, just letting me go. And then the waiter brought this tray with a silver tray and open it up. And there was the ring. And I was like, what? You didn't just wind me up to. And he got down on one knee in the restaurant and asked me to marry him. So he loves to tell that story. Because he was like, that shut you up, didn't it? I love it.

[Michelle Obama]

Let's give him a round of applause. You know, I love that so much. And I mean, so romantic. And the two of you are the. You guys are goals, you know, that you're marriage goals.

[Elaine Welteroth]

Well, that. But that's why I'm always like, we have trouble too.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

Because even when you have couples goals, marriage is hard.

[Michelle Obama]

Yep.

[Elaine Welteroth]

And it takes work. And I love him dearly. And I want all couples to understand that. That marriage is work. And it's work every day. Being a parent is work.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

As much as you want it, you know, bringing children into the world, the ones you want it, you know, it'll be the hardest thing you will ever do because it's the most important thing that you will ever do. And I don't want anybody to be blinded by that. So that's why I talk honestly about not just the highs, but about the challenges. Because I think people, young couples, give up too quickly when things get hard. And it's like, this is hard. This is a hard thing to do. Melding two lives together. Which is why you gotta be real clear in your choice.

[Michelle Obama]

Yep.

[Elaine Welteroth]

You know.

[Michelle Obama]

Cause even when they're the right committed man and you're in your mind and.

[Elaine Welteroth]

You'Re in love and all of it, it's all right.

[Michelle Obama]

It's still hard.

[Elaine Welteroth]

That's right.

[Michelle Obama]

So why make it harder going into the relationship where you aren't on the same page about what you ultimately want?

[Elaine Welteroth]

That's exactly right.

[Michelle Obama]

So I'm curious, I wanna ask you, because it sounds like you were the driver in getting the answers to those questions in the dating phase. What gave you the confidence, though, to, To. To. To really put that question to him and to be willing to walk away if. If he was not in alignment with you?

[Elaine Welteroth]

I think, like you, it was the other frogs, other relationships coming out, going, why didn't I. Why did I let that happen?

[Michelle Obama]

Yeah.

[Elaine Welteroth]

Why didn't I say more? Why didn't I? Why, why wasn't I clearer? That's why I believe in dating.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

Because you need practice. You know, you're going to get some stuff wrong. You're going to. You need to grow up just trying some things on, you know, and it. And be okay with things failing. Be okay with getting your heart broken, because you need to know that you can recover from that, too. So I think that it was practice made perfect. So I was a little more ready, a little more sure of myself, didn't have all the conversations. So, you know, there's still things I look back on 30 years, and I was like, did I agree. Did I agree to something in this marriage that I wouldn't have when I was 30 that I've got to renegotiate? And the answer is yes, because each decade we are learning something different. So you're never going to get it perfect. But I think knowing that this was a serious relationship and that this. That Barack was a serious person, I felt he left space for the questions. He wasn't defensive about the questions. And maybe that's. That's another cue for folks like Alice. You know, you don't want to be in a relationship with somebody that you can't have really good, hard, honest conversations. You don't have to get married to the person. But if you're dating, sleeping with somebody, if you're wasting your time with them or investing your time with them, she.

[Michelle Obama]

Said, wasting your time.

[Elaine Welteroth]

You know, then you should be with somebody that you can talk to. And if they're making you feel like you're intrusive or needy, that's a sign. I know that we lived together for a year before we got engaged. And I told Barack, I said, it makes economic sense for us to live together, but just know that this isn't a Forever thing. I don't. I don't want this to slip into years and years of living together, you know? So it's like, if you. If we're moving in together, then the next phase has got to be, we're getting engaged and we're going to get married.

[Michelle Obama]

How did he respond to that?

[Elaine Welteroth]

He was like, yeah, it makes sense. Makes sense. Which is why goading me with that question was a little annoying on our engagement night. Because I was like, dude, yeah, we already covered this. We covered this. But no, we were in alignment. And I knew that. And so everything felt right. I felt safe with him. I felt like there wasn't anything that I couldn't talk to him about. And that's how you're supposed to feel.

[Michelle Obama]

Yes.

[Elaine Welteroth]

And sometimes we have to ask ourselves as women and people, are we not asking the question because we don't really want to know the answer? Yeah. We want to be in pretend land.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

So I won't bring it up because the status quo feels okay. It's comfortable. So I will pretend like he didn't just tell me he didn't want kids. Like you said, when they tell you who they are, believe them the first time. Yeah. And don't be afraid of the question. And I want young women in particular to practice this part of their voice in relationships, to just practice asking for what you want and being clear. But then you gotta be okay with not getting the answer that you want. And I'd rather practice that feeling. Right.

[Michelle Obama]

Yep.

[Elaine Welteroth]

You'll survive it.

[Michelle Obama]

Yep.

[Elaine Welteroth]

No, it's okay to hear. No, it's okay to hear I don't love you like that. It's okay to hear we don't believe in the same things, or I think you're cute, but I don't want to get married. Know it early.

[Michelle Obama]

Yes.

[Elaine Welteroth]

Figure it out sooner. You know, press. Press it. And don't feel like it. Makes you look desperate. All it is, is you just want clarity.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

It's okay to want clarity. And that's different from being desperate?

[Michelle Obama]

Yes.

[Elaine Welteroth]

There's nothing wrong with clarity. Do not live your life in a fog. That's what I would tell Alice. You know, when you're 30 years old and you want things to happen, then don't waste your time with people and just ask the question. It's like, who are you? What do you want? What do you want out of life? Why don't you want kids? Let's have those conversations sooner rather than later. Now, that doesn't mean having them on the first date, Right? Right. You know, that might be a little too soon, but once you get to the point where you think you want to spend time with somebody, they should be able to handle these questions.

[Michelle Obama]

I believe absolutely. One thing that we haven't touched on that I think is embedded in Alice's question is this idea that there's an expiration date on her value as a woman and as a prospective partner. She's 30. She's realizing, okay, I wasted six years with this one. And I think that comes with this pressure to close the deal because society has told us that there is an expiration date on our value and that at some point men aren't gonna want us and they're gonna go for the 25 year old girl when they're 50. And listen, that's a phenomenon. We can't ignore that.

[Elaine Welteroth]

That's right.

[Michelle Obama]

But that doesn't have to define your value. And Alice has made the decision for herself that she wants to be a mother. So free. Free yourselves to get what you really want out of life. And I truly believe that's true love. That is true love. That is setting someone free to live the life that they really, really want. There's no higher love than that. And just because it comes to an end naturally doesn't mean that that time wasn't well spent and that you didn't learn and grow during that time. And it doesn't mean that it's a failure.

[Elaine Welteroth]

And live right. Yeah. Don't wait on life to come to you.

[Michelle Obama]

Yeah.

[Unknown]

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[Elaine Welteroth]

I would tell Alice, move on from this guy.

[Michelle Obama]

Yeah.

[Elaine Welteroth]

And don't just jump into the next thing. Work on you.

[Michelle Obama]

Yep.

[Elaine Welteroth]

Work on your dreams, your goals, your aspirations. Build your life independently. Use this time to make sure you're whole. Yes, you know and understand yourself because that's, I think, why finding love later can be better because you know more about who you are.

[Michelle Obama]

That part.

[Elaine Welteroth]

So at 30, Alice has got a lot of time to keep growing and let love find you as you grow. And if it doesn't, then you've just grown. You know, you're still at a good place.

[Michelle Obama]

Yes.

[Elaine Welteroth]

You know, you might not have love might not have found you, but you didn't stop your life waiting for it.

[Michelle Obama]

Yep. I will tell you, my mom has said to me from the time I was a little girl, a healthy relationship takes two whole people who gotta be whole on their own. And that is something that was, like, etched into my brain so. So early on that when I finally was mature enough, after the delusion I lived in. The one thing I want to admit to right here is that I did live in that delusion for a little bit where, yeah, I heard the answer, but I was a little bit like.

[Elaine Welteroth]

We all have done that in our.

[Michelle Obama]

Lives, so it's okay.

[Elaine Welteroth]

Yeah.

[Michelle Obama]

Mrs. Obama, you're not judging me.

[Elaine Welteroth]

No, not at all. Because I can. I can see those moments in myself where I was like, I'm gonna make him love me. And, you know, so we all go through that. Yeah, that's why you keep moving through it.

[Michelle Obama]

Yeah. But after that part, after the delusional chapter.

[Elaine Welteroth]

Yeah. Right.

[Michelle Obama]

Then I moved into this part where I really did fall in love with myself before I fell in love with Jonathan. In that in between time. That in between time is truly what I think set me up for a lifelong relationship. I think before that point, I would fold into the relationship.

[Elaine Welteroth]

That part. Yeah.

[Michelle Obama]

You know, and I would become what was good for the relationship. But this time that I spent in between Mr. Big and my actual husband, I cut all my hair off. It was so cliche. I chopped it all off. I decided I'm gonna live on my own for the first time. I'm gonna make dinner for myself every night. I signed up for a half marathon. I ran the half. The Brooklyn half.

[Elaine Welteroth]

Wow.

[Michelle Obama]

And along that timeframe, Jonathan came around. And at that point, I was like, you? I was like, I'm not really rushing into this. Cause I'm liking this. I'm doing me right now. And I'm tired of being in these. Being a serial monogamist. And it's almost like I had these mini marriages. And I was like, I just wanna be. I wanna be married to me.

[Elaine Welteroth]

And Jonathan had to catch up with you.

[Michelle Obama]

And you know who was waiting for me at the end of the finish line at that half marathon with Gatorade and some oranges? It was Jonathan. And he waited for me. And he said, don't worry, I'll be here. And it's that type of partner that's like. So that knows it's you, that will wait for you, that will show up for you. That feels like home. Like, that's the guy that you marry, ultimately. So I want that. I want that for. I want that for Alice. I want that for her. It's okay. Six years with someone, you're 30. That's fine.

[Elaine Welteroth]

That's okay.

[Michelle Obama]

But, like, what do you want out of life, make space for that?

[Elaine Welteroth]

Alice is wondering whether they're men who change their minds. I mean, yeah, people change their minds in life for sure. You know, I definitely know people who thought they'd never get married or thought they didn't want to have kids. So it is possible, if he's saying no, he can change his mind. But do you really want to wait?

[Michelle Obama]

Right. How long are you willing to wait?

[Elaine Welteroth]

Are you willing to wait to see if he would change his mind? I'm just afraid for her for what that question means. It's like she's wanting to wait. She's hoping, if she were my daughter, I would go, mm. Mm. Really? Uh, why don't you. Why don't you date? Why don't you just keep the door open? You know, if you thought about that, I'd probably ask a question like that.

[Michelle Obama]

Mm.

[Elaine Welteroth]

So I don't know. What do you think?

[Michelle Obama]

Have I ever seen a man change his mind about having children? I don't think that I have. I don't think that I have. I wasn't willing to wait around and see. Let me put that in my. In my own situation.

[Elaine Welteroth]

One of the things I say to people as they're thinking about picking a mate, you gotta think about, like, a partner as a member of your basketball team.

[Michelle Obama]

Ooh, I like that.

[Elaine Welteroth]

You know, it's like if you were picking players to play on a team, you wouldn't just pick a shooter. Everybody has to be able to do it all. Each person in a couple has to be able and willing to do it all.

[Michelle Obama]

Yep.

[Elaine Welteroth]

So you don't want to marry a man who's like, I don't cook. It's like, well, what happens if I can't cook right? You know, how are we going to survive? Yeah, you just don't do laundry. Life is so unpredictable and complicated. And then add in kids, right? If you're married to a man that doesn't do house chores and you've had given birth and you've had a cesarean, and you can't be on your feet, or, heaven forbid, you have a difficult pregnancy and you come home and he can't do anything. He'd never been grocery shopping, you know, or if you're the woman and you can't balance the checkbook because you've left that to him. Life is too complicated for two partners not to be real equals in it, you know, because you just don't know what's gonna come. You can make decisions throughout the marriage of who's Doing what? But everybody's gotta be able to do everything, especially when kids are involved.

[Michelle Obama]

Amen.

[Elaine Welteroth]

And so that, you know, you gotta look for a whole person and you've gotta be a whole person, you know? And I want men to hear this, and I want mothers raising men to hear this too. Teach these men how to be whole, you know, do not come into a relationship talking about what you aren't going to do, what you don't believe in, and men and women's roles. I mean, if it works out for you, great. But then don't let life happen to you.

[Michelle Obama]

Right?

[Elaine Welteroth]

Because then what?

[Michelle Obama]

Right?

[Elaine Welteroth]

You've never learned how to do anything other than the thing that a man is supposed to do. I wouldn't want that.

[Michelle Obama]

Dude, I'm curious. You have two daughters who get this, who've gotten this their whole lives. How have you seen this advice play out in your child's relationships? And have you been able to kind of see the fruits of all of your wisdom?

[Elaine Welteroth]

There's so, you know, I think like your mother, right. You don't know whether they're actually listening to you, you know, we're listening.

[Michelle Obama]

I want to tell you.

[Elaine Welteroth]

We're.

[Michelle Obama]

Listen.

[Elaine Welteroth]

I'm learning that now because now they're 26 and 23, right? And this is the age where I can see. Oh, you were listening, right. I lecture, I talk, we talk, we talk. That's all I've been doing with these girls, talking and talking honestly, making sure that they feel like they can ask me anything. Which means, like your mother, you gotta learn to have that poker face. Because if you get, if you get too involved, then they don't come back. So I spend a lot of time, especially when they went away to college and living on their own conversations or this really. Whoa, wow. Tell me more. Right? It's like they're like cats. Don't hold them too tight, don't squeeze them, because they'll never come back. I try not to be too judgmental, you know, I try not to be too heavy handed, but I, but I talk to them in the way that I'm talking to you. I share the mistakes that I made. I share the things that work in our marriage without getting them too involved, right? Just making sure they're seeing the good, the bad. They know that I'm human. They hear my stories, so they feel like they can tell me theirs. And the real learning comes in these kind of conversations, right? Choices that they're making so far are ones that I'm like, okay, yeah, all right. Not, not Always perfect. But watching them turn the corner and understanding their worth. So I just want my girls to be open and to use their voice in relationships. It is scary to let your kids make their own choices and to suffer their own consequences, you know, Especially when you know better. Especially when you know better. Oh, my gosh. It's just like, I've done this, you know, I'm raising my hand in the room. It's like, I know the answer. You guys look at me. Pick me, right? I can tell you this. I really do know. And, you know, they have to hit the wall.

[Michelle Obama]

You know, I wouldn't be the mom that I am if I didn't have the kind of mom that I had. And it sounds like you guys are definitely playing from the same mom playbook.

[Elaine Welteroth]

You're doing good. You're doing good. Well, I think that if we could sum up our advice to Alice, we've had a full throated conversation. I think what would you. If you had to give three pieces of advice that summed up what you think Alice should be thinking about, what would you tell her?

[Michelle Obama]

Well, I'm gonna take a page out of your book, and I'm gonna use an analogy that I yesterday that was about writing a book. So basically, making hard decisions about your life is kind of like driving a car in the dark with headlights on. You can only see but so far in front of you, right? Like, the light only shines just so much in front of you. And you can make the whole trip by just making the best decisions based on what you can see right in front of you. You don't need to be able to see the whole road. Even when the rest is dark, you can see this much. And so I would say make the best decision for your life based on what you can see from where you're sitting right now. And if you can see that this man doesn't want what you want in the long run, it's okay to pivot. And I think your life is going to be full of beautiful pivots. You don't have to stay on the road that you're on just because you traveled it this far. You can make a left turn and you don't have to be a ride or die. You don't gotta die. Okay, Just to ride. You can say, this has been a nice.

[Elaine Welteroth]

I wanna live. I don't wanna ride and die.

[Michelle Obama]

I don't wanna die.

[Elaine Welteroth]

Yeah. Yeah. So what's the point of being a ride or die.

[Michelle Obama]

What is the point? Cause I don't actually wanna die. So the ride has been nice right to this point, sir.

[Elaine Welteroth]

I'm getting off, right?

[Michelle Obama]

And this is where you can let yourself out. And I'm going that way. And I think just allow yourself. And I know it's so scary when you can't see what's ahead, and you're like, does this mean I'm going to be alone forever? Will I ever find somebody that loves me this much? We've invested so much time. Like, I overstand all of that because I have lived it multiple times. But you got to just keep making the best decisions based on what's right in front of you and trust that what is in the dark will come to the light. And it could be even more beautiful than you could ever imagine. So that would be my closing statement.

[Elaine Welteroth]

I love that, Alex. And your mom is gonna hear this podcast conversation, and you know what she's gonna say?

[Michelle Obama]

What is she gonna say?

[Elaine Welteroth]

She gonna say, oh, Lord, you told.

[Michelle Obama]

Your business to the whole world and.

[Elaine Welteroth]

To Mrs. Obama, she is gonna say, wow, you know, I knew. I knew Lainey had it in her, you know, she was listening all this time, you know, and that's the beauty of parenthood. That's some of the proudest moments you'll have as a parent. And for Alice, if motherhood is something that she wants, then I wouldn't give it up. I wouldn't give up that dream. Not at 30. You know, I want Alice to know she's young. There is time. People are becoming mothers later in life. I would encourage her to look at freezing her eggs. Just give herself some time, but do not settle. Do not try to force somebody into a life that isn't for them, because marriage and family is hard enough. So you want to do it with somebody who wants what you want as much as you want it. Amen. And you shouldn't have to talk somebody into your dream. Ask for what you want. Find out the information you need. Don't allow game playing to take over the dynamic of the relationship, especially as we get older. We just don't have to. Ain't nobody got time for that.

[Michelle Obama]

Ain't nobody got time for that.

[Elaine Welteroth]

So find out what you need to know. And if you're with the right person, those questions won't be intimidating. And if they are, that's a sign that that person's not for you. If they can't answer some basic questions, if you can't have some good conversations about life and exist expectations, then that's a cue that. Just date them. Don't marry him. You know, But, Elaine, thank you so much for this was. This filled me up. I'm really proud of the woman that you have become. So thank you for taking the time.

[Michelle Obama]

Thank you for the joy of being able to share some of these stories with you. And. Yeah, I just feel so blessed by this conversation. My heart is so full. You got me out here about to cry. I don't know if it's the hormones, but thank you. This was such a beautiful conversation.

[Elaine Welteroth]

I'd love to get you back.

[Michelle Obama]

Thank you so much.