Elaine Welteroth

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. Okay. Let's hear it. Okay. You promise. I don't know.

Was it the breakup? Jonathan. 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.

Because a lot of people...

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 just so you know, just so you know, Mrs. Obama, I did not know the man's age when we started dating. See, I'm not feeling him, this guy.

You're like my mama. My mom told me this summer, finally told me, she said, that was one of the hardest times in my life as a mother. I'm sure it was hard for her to watch you go through that. And I was like, mom, you acted like you were fine with it. She was like, that was an act. That's exactly what that was.

Okay. 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 really, I want an enthusiastic partner in that.

Look who's talking.

And I will not have that in this man. I don't want to pull somebody kicking and screaming into parenthood. 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. Good for you. And so I packed up my clothes. Mm-hmm.

And I left one day. And you were living with him, too. I wasn't living. I was just staying over there a lot. Okay, all right. I had my own apartment, okay? I was an independent woman. I was like, and you were staying over there. No, no, 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. Yeah. And do you know that I reunited with Jonathan, this kid from church. The church boy.

That you overlooked and looked right past Jonathan. I sure did.

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

The nice ones.

Right?

What is that? What is that? I had that. I had that syndrome. But we got to go on our own journeys. And, you know, I will say I'm so grateful for all the frogs I kissed before meeting what truly is my version. Not to be cliche and cheesy, but my version. Your real Mr. Big. My real Prince Charming. Yeah. And I will tell you right away, I felt at home. 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 peace. Say that again.

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. Wow. I think 32 weeks pregnant today. Wow. Congratulations. Thank you so much. This is the perfect way to bless the bump before we get into that final, final stretch.

Woo! You're preaching. Yeah, yeah. So did you two speak about these things early in your dating life? Did you ask, do you want kids? Did you ask, do you want to be married?

Oh, he was one of those.

You got to choose who you're going to do it with.

I love it. 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.

Yeah.

Yeah.

Yeah.

Yeah.

Yep. Because even when they're the right committed man and you're aligned and you're in love, it's still hard. That's right. So why make it harder going into the relationship where you aren't on the same page about what you ultimately want?

So I'm curious, I want to 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 really put that question to him and to be willing to walk away if he was not in alignment with you?

Yeah.

The first time.

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, Thank you. Thank you. Thank you.

It speaks to 25-year-old me, it does. Really?

Thank you. Thank you. Thank you.

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. Okay. Let's hear it. Okay.

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 with them?

Let's just say this is one of those things. Okay. This is one of those things. So when I was 25, I found myself in love with a 50-year-old man. Okay. All right. And this 50-year-old man already had children. And at the time, you know, I really wasn't thinking about children.

We're listening. I want to tell you, we're listening.

Yeah.

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.

Well, I'm going to take a page out of your book and I'm going to use an analogy that I just read 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 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. How long were you dating before you... It came up 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, maybe there's still a chance, right?

And if you can see that this man doesn't want what you want in the long run. Yeah. 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 got to die. Okay. Just to ride. You can say, I want to live.

I don't want to ride and die. I don't want to die. Yeah. Yeah.

What is the point? Because I don't actually want to die. So the ride has been nice to this point, sir. I'm getting off. 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. 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.

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. Well, I'd love to get you back. Thank you so much.

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, or in this case, tells you who they are, Believe them the first time. That's right. 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. Mm-hmm.

A year.

I have the same question now. Looking back as a 37-year-old woman, I have the same question now. Right.

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 got to 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. That's right.

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

And yes, 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.

I know. Well, let's talk about that. Well, I do think there's 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 kind of the waiting.

And that was my Mr. Big. That was my black Mr. Big. 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 like- The breakup with the older guy. 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. That's what I'm, yeah. Right? And it was like this idea that some man is going to 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 got to 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. Yeah, that's right. And we're subscribing to this notion. Yes. 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.

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