In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Jessa, 36, and Charles, 44, met on the same night that Charles got arrested, and it only got more dramatic from there.
Charles: I was living in the Midwest. There was a big lake nearby, and my friend had a boat. It was rainy and I wasn’t planning on going, but my friend was like, “There’s going to be, like, five girls there. You’re coming.” Of the five girls, the prettiest girl on the boat was Jessa. I knew my friend and cousin were going to charm her hard. So I ignored her all day. I didn’t speak to her. I did the whole the girl you’re most interested in, you pay the least amount of attention to sort of thing.
Jessa: I didn’t want to go, but my friends persuaded me to go on this boat. I look at these two guys getting on. They seemed high out of their minds. Charles had a stupid BMW shirt on. He kept flirting with this other girl. I was pretty miserable the whole time.
Charles: We always had a sober boater. This weekend, it was not my turn to be the sober boater, so I indulged in quite a bit of alcohol, as did everybody. It turned into a dance party.
Jessa: He started to flirt with me when I took over the music. Everyone was listening to Britney Spears. Then I put on LCD Soundsystem. He was like, “Oh yeah.” That’s when we were like, oh we might be sort of on the same page. I got a vibe. No one else on that boat knew LCD Soundsystem.
Charles: I’m still paying no mind to Jessa. I had not even talked to her yet. As we approach our dock, the sober driver says he wants to do a cannonball off the boat, so I sit in the cockpit for a few minutes … and suddenly we get pulled over by the Coast Guard. I’m visibly intoxicated, so I slide out of my seat and find myself sitting next to Jessa, who I have not spoken to for the whole day. I know I’m about to get arrested for boating under the influence, and before they take me away, I say to her, “Well, it was really nice not talking to you this afternoon; if you ever want to get dinner, here’s my number.” I took her phone and typed it in. Moments later, I’m cuffed and being dragged downriver to boat jail.
Jessa: He gets arrested. His cousin is like, “Can I get your number?” I was like, “No. But you can give me Charles’s number.” A few hours later, the police officer contacted us and was like, “Someone has to get him.” I’m like, “I’ll go pick him up.” I had my car at the dock. So I let myself sober up, then I went to get him.
Charles: An Uber pulls up and who’s in it but the pretty girl I’d been ignoring all afternoon.
Jessa: My car was filled with plants. It’s the opposite of Charles’s car — a slick red BMW with a gross red-leather interior. He was in finance. I’m an artist. I had plants. I had dogs. He hates dogs. Everything was opposite from the start. He gets in the car and was like, “What the fuck is with the plants?” I was like, “Um, you’re welcome.”
Charles: We stayed out all night, met up with friends, and at the end of the night I looked at her like, “You know you’re staying over with me tonight, right?” We closed the deal a few times that night. There was an animal energy between the two of us. We were very attracted to each other.
Jessa: We had sex that first night. I don’t remember anything about our sexual connection that night, honestly. But from day one, all my friends were like, “You should stay away from him. He’s crazy.” But also from day one, everyone was like, “Yeah, this kinda makes sense.”
Charles: Everything changes the next morning. I was like, tell me your life story. She says she just quit her job and is moving to South Carolina.
Jessa: I was moving to North Carolina.
Charles: I tell her I’m actually going to be moving to Boston in the fall. It’s a bummer. As we catch up, we find all these other similarities. We even put together that we met years ago, and I hit on her, and she had a boyfriend. It was like, God has put us here. The sky has fallen. Like what is going on here? She’s crazy like me. I mean, clearly she’s half-nuts because she just bailed a guy out of jail and spent the night at his house. And we just became infatuated with each other. We were always making out. We couldn’t keep our hands off of each other.
Jessa: I didn’t give a shit about anything or anyone, but I had fun and I was always super-happy. I worked at a coffee shop, and Charles would come to my work and be like, “How much money are you going to make today working?” I would say, I don’t know. And he would hand me the money he thought I would make and say, “Leave right now. With me. Let’s get out of here.” It was really sweet. With him, I had the most fun I ever had in my life.
Charles: Within a week, I was like, you’re not going to South Carolina, you’re staying with me. By the end of that summer, I told her I was in love with her. I fell head over heels. I was 30 and she was 23. She was a baby. But I wanted her with me. I couldn’t live without her. I needed her by my side.
Jessa: There were red flags early on. With all the fun came a lot of not fun. He has anger issues and drinking issues. He would be sneaky. I found out he was going to Boston and had been hiding it from me. He said he wanted me to come with him. Intermittently, he would stop drinking. He would do some therapy, but I think he lied to the therapist about his behavior.
Charles: I was like, move to Boston with me. I had a job opportunity there. I want you to experience life with me. We met in June; I moved to Boston in December. Jessa moved in January.
Jessa: I was going to North Carolina for a guy. But I didn’t have strong feelings for him. So I went to Boston with Charles, but it was already a roller coaster. We would have really bad fights, and then he would always apologize and feel so bad and buy me gifts and make up for it. This turned into our whole relationship. I knew he loved me and cared about me, but his drinking and rage … it was just a lot. He wanted me to dress more “Boston.” He bought me some J.Crew. I was losing who I was.
So I decided to move out. Then I went to work and I just started puking all day …
Charles: By Valentine’s Day we’d known each other for eight months and she tells me she’s pregnant. I think this was the beginning of the end of the relationship. Because I looked at her and said, “Is it mine?” I was such a narcissist. It was such an asinine thing to say. Clearly, it was mine. I was raised Catholic, and I knew the right thing to do next was get married.
Jessa: It wasn’t a happy conversation. Then he kind of disappeared for a couple days.
Charles: I said that terrible thing, but after that, I did all the right things. I went shopping for a wedding ring. I asked her parents and her siblings if I could propose, and they said “yes.” I picked up the ring, marched across the Boston Common, walked into the boutique she was working in, dropped down to one knee, and asked her to marry me.
Jessa: He just walked into my work and proposed to me. It was so uncomfortable. But I was like, “Okay.” I felt trapped, and shocked, and very scared about everything. He was like, “I know you’re scared, but I’m going to take care of you.”
Charles: I was scared shitless, no doubt. But I was making a lot of money. I had a good job. I loved this woman. I was like, “We can do this.” I genuinely believed we could do it.
Jessa: We fought all the way to the courthouse.
Charles: On the way to the courthouse, it was still the honeymoon period. I was so in love with this person.
Jessa: We had a small celebration with friends afterward. He obviously got wasted. I cried in the bathroom for two hours. But I will say, I think Charles was pretty happy. He felt better about it than I did, for sure. There’s a wedding picture of him whispering in my ear — it’s a sweet picture, actually — and saying, “I’m going to take care of you.” I’m three months pregnant at this point, and I just felt gross. But Charles looked terrible too … it’s not funny, but it’s kind of funny! We were both so bloated.
Charles: A few months later, Jessa is very pregnant. We go on vacation with my family somewhere down South. We had a couple cocktails with my mom and dad. Around 5 a.m., I hear my mother screaming, and my father is on the floor having a heart attack. He’s dead. My pregnant wife is standing in a corner bawling. I’m in a state of absolute shock. My father has just died in front of me. And I’m not going to lie, that fucked me up pretty good.
Jessa: It was horrible. This was actually the point of no return. Everything just went away for us.
Charles: We eventually go back to our life in Boston. We have our first child. At this point, I’m a full-blown alcoholic. I didn’t know how to deal with anything that’s just happened to my life. I was hell-set on destroying what I had created, subconsciously. I was like you have to blow this up, you have to destroy this.
Jessa: He totally 100 percent abandoned me emotionally after that.
Charles: We fought mercilessly. About everything. I would come home late and I’d be drunk. She was like, “I’m 25 years old, home alone with a baby, what the fuck is wrong with you?” And I didn’t get it. I was like, “I make all this money; I put you in this beautiful home. Hire some help! Deal with it.” I was a terrible person.
Jessa: I really just want to remember having my baby as a happy time. But the truth was, it was pretty bad. His drinking. The fighting. It was exhausting and isolating. My friends were exhausted by my relationship issues. They didn’t want to hear it anymore.
Charles: Six months later, Jessa and our baby left. They left me. She moved home to her parents’ house in the Midwest.
Jessa: We got into an insane fight. Details I don’t want to think about or talk about. Police were involved.
Charles: I engaged with a lawyer; we started the divorce proceedings.
Jessa: I moved out with the baby. I was stick-skinny. I was depressed. We were both trying to take each other down. I just had to get well to take care of my baby.
Charles: I was just so fucked-up. I was like, “I’ll send her money. Whatever.” Those days were dark.
Jessa: A year passed, and I started thinking about forgiving Charles. Things had settled. He was better with his drinking. He was showing that he was working on himself. But it was time to sign our divorce papers. That’s when we started sleeping together again.
Charles: We meet up to finalize the divorce and we go out to dinner, we get drunk, we go home, and we make baby No. 2.
Jessa: And I’m pregnant. Again. Charles was so excited. I’ve never seen him so excited, ever. He’s like, “This time we’re going to do it right. This is our second chance.”
Charles: We didn’t even talk about termination. We, romantically, still believed we were meant for each other. We got back together. We tried to hit the reset button. I don’t know what the fuck I was thinking. I was not in my right mind. This was not going to fix anything. Having another kid would only complicate it.
Jessa: Because I’m an idiot, we moved back in together.
Charles: At this point, I knew that Jessa was a tremendous mother and that she could handle anything. Me? I was still a piece-of-shit alcoholic who was toxic in every way.
Jessa: We had another baby. It was definitely better. We found more windows of happiness. I built more of my own life. I was working as a successful artist. I was running marathons. I focused all my energy and love on the kids and we did have a great time. But Charles was still always drunk. And now I’m basically alone with two kids all the time.
Charles: We needed a change of scenery. So I asked my boss to move to a new city, and he agreed.
Jessa: He did that for me. I wanted to move. When he’s wonderful, he’s the best fucking person alive. But we got to the new city and he spiraled. The partying got worse.
Charles: It was supposed to be a new chapter for us. Now I was the one who stayed home and babysat while she went out. And I resented it. One night after Jessa was hanging out with her girlfriends, I was drunk and pissed off and I accused her of cheating … it was a really bad fight. It got extremely ugly. I walked out of the apartment. It was the lowest I’ve ever been. That night, she threw me out.
Jessa: It was 4 a.m. He had been partying with friends in our apartment while the kids slept, and he was out of control. I packed up the kids. This was rock bottom. There was no turning back at this point.
Charles: I moved in with a friend. For a year, I sobered up. We tried marriage counseling. We got fired by three marriage counselors. The last one said, “You just need to end this.” That’s when we decided to finally get the divorce and make it go away. I felt like a failure.
Jessa: It’s been a few years since the divorce, and I only very recently have started to feel better. I kind of blocked Charles out other than logistics with the kids. I completely disconnected from him. I started getting the right kind of help. My friends have helped me so much too. My girlfriend got me an amazingly creative job. My friends have helped me with child care. Thank God for girlfriends.
Charles: I took time to focus on mental health and sobriety. I was so broken from losing my father. I had to get myself right.
Jessa: I think we’ve both grown. He still drinks, but it’s definitely not as bad. All he’s ever wanted was my support, and I was like, “I’m a mom and you’ve broken me down, and I can’t do it anymore.” We started our foundation with nothing, with partying. We were so immature.
Charles: I’ve since had two semi-relationships. I never met anybody’s parents. We went out to dinner and made out, that kind of stuff. Jessa dated a couple of different guys. Nothing worked.
Jessa: I don’t know if he’s older and tired now, or matured finally … but I think we’ve both dated people and realized that no one is perfect. It’s funny in doing all the work I’ve done on myself, I’ve come full circle back to Charles. I’ve finally forgiven him. I mean, we’re getting brunch this weekend. I’m very, very, very hesitant. But there’s no stress anymore. I honestly don’t know what’s going to happen. I mean, I love him. I can’t stop the feeling. But also, I’m terrified. I told him I need to take things extremely slow.
Charles: Over time, we softened. We became civil. We started doing more family dinners. We just got better. We both matured significantly over time. We became less antagonistic. I don’t know where we are now. We are still incredibly attracted to each other. There’s been a few sleepovers. A few dalliances. We are at a much healthier crossroads in our lives now. I’m optimistic. I never want to blow us up again. It was so terrible. But when I’m with her, I’m still reminded of why I married her. I look at our kids and think, I’m so happy this is the woman I had a family with. Who knows, maybe there’s a round three. Our story is a beautiful one … but only if the ending is happy.