both sides of a breakup

She Got Pregnant on the First Date

Illustration: by the Cut

In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. After Annika, 45, and Tom, 35, slept together for the first time, they became attached to each other forever …

Annika: When I met Tom, I was at a major crossroads. I was 42 and had no idea where to turn. I had about eight boyfriends in my 30s who all turned out to be shitheads, and I felt old and unwanted. It was not a great time. Work was thriving — I’m the creative director of a global beauty brand — but I was embarrassed to be me. You know, the girl who always has love-life drama. It’s not cute in your 40s. I felt old and achy, so I signed up to work with a personal trainer at my gym.

Tom: I was living it up, ya know. I was in my early 30s, staying fit, playing basketball every day, getting a law degree and doing personal training to pay the bills. There were lots of ladies. I wasn’t looking for anything serious. I wanted to enjoy my life. When I met Annika, I only had professional thoughts. I mean, I clocked that she was an attractive older woman, but I always turned that part of my brain off when I worked. I still do. But after the first session, we started texting. I do this with some clients. It’s just a perk of working with me; I’m there to talk about general wellness, not just the problem at hand.

Annika: I remember him texting me after our session, which I thought was inappropriate, but it also got me excited. Tom is very hot. And I know this sounds like I’m a gold digger, but his parents were both very successful and quite wealthy, so I guess that made me take him more seriously. Like, he comes from money, he’s going to be a lawyer, who cares if he’s ten years younger than me. Anyway, the texts got more and more frequent and I was totally crushing on him. I actually never saw him as a trainer again because I felt awkward about it all. I wanted to transition into potentially dating him. I didn’t want him to see me all sweaty and flabby.

Tom: I think we trained together for a few weeks or months. But I knew she had a crush on me. I liked it. I tend to desire the attention of females. It makes me feel alive. A month or so after meeting, I asked her to be my date to a law-school party.

Annika: He asked me to this school function, as his date. I felt so nervous about it. I was way too old to go, but also I had butterflies in my stomach. I remember my friends were all like, “Fuck it. Go with him! Have fun!”

Tom: I think I asked her because she was the most impressive of all the women I was dating. Some of them were like … yeah, no, you can’t bring those girls around.

Annika: We had a great time. The only thing was, Tom got very drunk. I want to say he had seven beers or something that night.

Tom: We both got trashed and ended up going back to her place. It was a gorgeous apartment. It smelled like flowers. I remember she had really good food in her fridge and like, half a pie just sitting on a cake plate. I was pretty plastered, but I remember thinking to myself, Wow, this is a real woman. But whatever, we had messy sex that I barely remember, but it must have been pretty nice because I slept over and then we had more sex the next day. I liked her, but I also really liked her sheets and how clean everything was. Every room smelled pretty. I know this makes it sound like my apartment must smell like dog shit, but it doesn’t! It’s just that Annika was domestic and refined in a way most of my girlfriends weren’t at the time.

Annika: It was a fun night. Tom was sexy and the actual “fucking” was good. But I woke up with a gut feeling that he was not the man for me. I really wanted to settle down and have kids. I had frozen my eggs. I was too smart to waste time with someone like him. And that level of drinking really worried me. I have a long history of addiction in my family and I generally don’t mess with that. I’m not saying he had a drinking problem, but the seven beers was a red flag, at least for me.

Tom: We didn’t talk much after that night, but then I got a text from her that we had to meet up ASAP. It felt like I was in a movie. I just knew what was happening …

Annika: So … the night Tom and I fucked, we did it a bunch of times, and sometimes we used condoms and sometimes we didn’t. There were a lot of “just the tip” moments which then led to him putting a condom on, but … we played with fire. And surprise! I got pregnant. It was a pretty classic realization. My period was late. My tits were aching. I took a digital test and it popped up: PREGNANT. I can’t tell you how I felt. Numb. Terrified. All the things. I paced around my apartment for like 20 minutes and called him and said we had to meet up that night. I could barely talk. My voice was shaking. I honestly had no idea what to think about any of it. But, I have to be honest, there was also a part of me that was like … “Holy shit, holy shit, holy shit, I’m going to have a baby!” And the thought of that was both overwhelming and overwhelmingly joyful. It was a lot.

Tom: She told me the second I sat down.

Annika: I told him to have a drink, and drink it all, before I said anything.

Tom: She told me she was pregnant, and that she didn’t think she wanted to have an abortion, and I was just stunned. I have three sisters, so I tried to be the man I would want to be sitting across from them. I did a lot of listening and I told her that it was her body and her choice and I would be as respectful or involved or … basically, I was like, tell me what to do and I’ll do it.

Annika: He was actually very sweet in that moment. It was not textbook in any way. He was kind and maybe even a little bit excited about our potential future as … what? Co-parents? We weren’t a couple. We decided we would try to be a couple, though. It was kind of transactional. Like, “let’s see if this pregnancy sticks” and let’s start dating as we go.

Tom: I was fully in! Who would have thought it! I think, subconsciously, I was like, This is my chance to prove to the world, to myself, that I am capable of something so “adult.” Like, maybe it was an ego thing for me. But it was also a gut intuition thing. I was kind of in love with my daughter from the second Annika told me the news.

Annika: It was still too soon for ultrasounds and whatnot, but we started going out almost every night. I was not drinking, obviously, but I noticed how much Tom relied on his beers and his wine. He was almost never without a beer. I did not like it. When I asked about it, he said he came from “WASP”s and WASPs drink. I tried not to make a big deal about it.

Tom: Annika will always say I drink too much. I don’t. I have no other vices. I don’t smoke cigarettes or gamble. But at the end of the day, I like a cocktail. Or if I’m watching sports, I like a beer. It’s very, very normal.

Annika: As the pregnancy progressed, I started to get an idea of how we could co-parent. We weren’t falling in love. And I was so fixated on his drinking that I could barely kiss him anymore because the taste of the alcohol would turn me off so much. But he was a wonderful partner in other ways, and really rose to the occasion in ways I never would have predicted. He was very nurturing. If I had a ramen craving, he brought ramen. There were fresh flowers delivered often. He let me steer the ship on everything. If I wanted him at a doctor’s appointment, he found a way to be there. If I didn’t want him there, he was understanding.

But I just knew we weren’t meant to be a forever couple. Why prolong things or pretend?

Tom: When she was, like, six months pregnant, she kind of broke up with me. She said she wanted me to have other girlfriends and continue to have fun, but she really wanted to raise our daughter together. Her plan made sense. I did feel rejected, I guess. I wanted to be the man she wanted me to be. Were we in love? I think so. It was a totally crazy kind of love story. Seriously, right out of the movies! But I continued to respect what she wanted. So we stopped being a couple.

Annika: I know it was hard for him. He asked for a gray area. He suggested we keep dating but just pull back a little, and tried to come up with alternative ideas for us to “keep trying.” But I’m a black-and-white person. I knew the decision to be friends, and only friends, was right for him, for both of us.

Tom: It was sad for me. I was lonely without her. We hadn’t moved in together or anything, but we were always at her place and it was starting to feel like family. It was hard to go back to dating with no strings attached — plus, I had a daughter on the way. I was pretty confused at the time.

Annika: He started drinking a lot. He would get into fights with random people at local bars. He was a mess without me anchoring him. As my pregnancy got further along, I knew I had two choices: to hate this man for his behavior and his issues, or to try and fix things. So I got us into therapy. At about nine months pregnant, we went to couples therapy even though we weren’t a couple and I never wanted us to be a couple. Our story is so weird, I’m telling you!

Tom: Therapy was good for me. We went like three times. It brought up some family stuff. I really did not want to be a sober person, but I got a handle on things. I don’t drink in front of Annika anymore. It triggers her and upsets her; I won’t do that.

Annika: We went to therapy about five or six times, but then … I had the baby! And who has time for anything after that. Our daughter was born two years ago. It has not been easy, life as a single mom, but Tom is an excellent father, and our families help us, and my work has been enormously supportive of me and my journey.

I love Tom. I wouldn’t date him again for all the money in the world, but meeting him turned out to be a great blessing. Every Sunday night, we look at our weeks ahead, and figure out who can do what, who can manage what. We try to help each other when there’s a work situation, or if the other wants to go on a date night. It’s fluid and open. Doesn’t hurt that we have a part-time nanny and apartments nearby — all because of Tom’s contribution to our family, financially.

Tom: My daughter is my heart and soul. Annika is a terrific mom. She’s still a pain in my ass with the drinking, but we make it work. We are happy and making the most of an untraditional situation. I am dating someone, but she has to understand that my daughter comes first, and I’m not sure if she’ll be able to accept that.

Annika: I haven’t dated or slept with anyone since Tom. Soon I’ll get back on my feet, but there is no time or energy for that right now. I don’t really care. I love being a mom. It’s hardly perfect, but I love our crazy family of three.

Both Sides of a Breakup: She Got Pregnant on the First Date