Confessions of a Serial Cheater (Who's About to Get Married)

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Photo: Courtesy of Mary Boone Gallery New York

As told to Alex Morris

Do I remember the first time I ever cheated? You would think I should, right? I remember the first time in the relationship I’m in now. There was a girl staying with my roommate, and for some reason she was infatuated with me. I mean, she was not attractive at all, but she was nice, and she wanted me really bad. She’d thrown herself at me earlier in the night at a bar, and my roommate had told me, “Just do it, just do it.” And so I was in my apartment, thinking, She’s in the other room right now, and she wants to have sex with me. So I just walked in the room, and she said, “Hello,” and I closed the door and said, “Take off your clothes.” And she did. It was kind of awesome. Before I started dating my now-fiancée, I planned on being single for a long time, just sowing my wild oats. But then I met her, and there was nothing I could do. I started to fall in love with her, and I wanted to be exclusive. So I told myself when we started dating that I wouldn’t cheat, but that obviously didn’t last very long. How many people have I cheated on her with since? More than ten, fifteen, maybe twenty.

I’ve only been faithful in one relationship. It was with one of the first people I dated, but when she was breaking up with me, she told me, “I was cheating on you a lot, so this isn’t going to work.” I wasn’t annoyed. I wasn’t even hurt or insecure. I felt like I had missed out, that I could have hooked up with people, too, and I turned down all these opportunities with great girls.

There’s something amazing about someone new. It’s just like a discovery. When you’ve been with someone for so long, they have a very distinct touch. You know what you’re getting into when you start to kiss that person and touch her neck, her back, her shoulder, her waist. You know what it’s going to feel like. You may love it, and it’s beautiful and wonderful. But you know everything.

When it’s someone else, you’re exploring somewhere you’ve never been, and your heart is racing, and you can feel the excitement in her as well. I think that is really amazing. Just having that. If I go a certain amount of time where I haven’t been with anyone new, I start to feel like I’m bottling something up.

For the most part, it’s been one-night stands here and there. I try not to initiate. I would feel worse if I actively sought other women out. But I can’t say that I’m not guilty of seeming open to it. The first thing out of my mouth isn’t “I have a girlfriend,” but if I got asked the question, I wouldn’t lie. For some reason, I feel wrong about lying, but I’m fine with leaving out the truth.

Bill & Anita 1980, Credit: Courtesy of George Eastman House and The Estate of Ted Spagna From the book Sleep by Ted Spagna/Rizzoli New York; release: September 2013.

There is such a thing as respectful infidelity. That’s one of the things that I always think about. As much as I’ve been unfaithful at times, I’ve tried, as respectfully as I could, to do it without hurting anyone’s feelings and getting caught. You keep your phone history clear or blacklist numbers from being able to call you or text you. Also, don’t shit where you eat. Sure, it’s much easier to go and have sex with your secretary than it is to leave town and go somewhere and meet someone randomly, but New York City’s big enough where you can meet someone who you will never see again. Anybody from work, those people have to be off-limits. And I’ve never been with a married woman.

There are things you reserve for the person you love, like spending the night in that person’s arms. I’m not going to be unpassionate with someone I’m cheating with, but I won’t spend the night. Everybody draws the line somewhere, and that’s where I draw mine. Of course there have been “Oh, shit” moments. One time I was out drinking with friends, and I got so drunk and wound up waking up in a girl’s apartment. She was in a bra and panties, and I was in my shorts but no shirt. She was asleep. I was still drunk, and the sun was up. I bolted out of there.

I have gotten a hotel and not spent the night. And I’ve gotten, like, midday hotels. One time, we just wanted to make it happen, and it was like, “We can’t make out in the street. We’re going to go to a hotel for an hour, and then I’m going to go home.”

I also don’t go down on other women, because I want less intimacy with the people I’m cheating with, and going down on a woman is one of the most intimate things for me. Using protection is very important. If you don’t know someone, you can’t not use a condom when you have sex with her. I mean, you can, and you might get lucky, but you’re being more of an asshole. You can limit how much of an asshole you are, you know what I mean?

My best friends in the world know that I cheat, and I think most of them are on the same page. A few of them are in relationships and have a similar kind of thing that they do. I just think guys are more likely to understand the fact that guys go through this, whereas it seems it’s something girls have a hard time understanding. Like, I’ve had female friends say to me, “How could a guy marry a girl that he has cheated on? Why would you want to be with someone if you want to cheat on her? Don’t you think that that’s not the right person for you?” They don’t understand.

I mean, my parents don’t have a perfect relationship, but I guess I know my dad well enough to know that he doesn’t cheat on my mom, and he never has. My mom, I think, is the same. I don’t know what made me this way. The guys who don’t cheat, it just doesn’t seem like a battle for them. It’s not like they’re saying, “It’s really fucking hard for me, but I don’t do it.” It mostly seems like they’re wired differently.

I feel like we’re raised to think of love as this fairy-tale thing where she finds Prince Charming and he finds the princess. That they’re the only ones in this world meant for each other because everybody else is a bunch of gnomes and witches. But maybe you could be a match with none of them or maybe you could be matched with so many of them. So, I don’t know.

I do deal with guilt. The guilt is always looming. One of the biggest problems with being a cheater is that there’s some level of intimacy that I can’t have with my fiancée. If I get a call from her and she’s crying, my heart will stop because the first thing I’ll think is that she’s found out about what I’ve been doing. I initially have this selfish reaction, which is horrible. But then she’ll say, “Oh my God, I failed this exam,” and I’ll breathe a sigh of relief before saying, “That really sucks.”

But since the guilt is already up there looming, it’s like, “What the hell does it matter if I add a few clouds to the storm? The storm’s there.” You go and have sex with a woman at a hotel, you shower and clean off, and you go home. Then you kiss the woman who you actually love—usually she’s asleep so I don’t have to do that until the next day. But if you can’t kiss that person or still love that person, then you really shouldn’t be doing it. If it’s going to negatively impact your relationship at home, that’s even more fucked up than being able to say, “That was something that I got out of my system. Now I have to pay attention to the woman I love.”

When I’ve gone a long time without cheating, I’ve started to feel almost bitter toward my fiancée because I’m not allowing myself to go and do what I needed to do. With her, my emotional needs are met. Our sex life is great. But oftentimes, after having something else, I enjoy going back to her more. It sounds so weird, but we work better when I’m cheating. Other than the feeling of guilt, it alleviates the pressure in our relationship.

Do I think my fiancée has ever cheated? I don’t know. It’s totally a sexist thing to say, but it just seems like men can do detached sex so much more easily than women can. But it would hurt, definitely. I want to say I would be able to forgive her and we’d be able to talk it out and I would be able to tell her about my own situation. And maybe I would feel a little relieved that I’m not the only one who wasn’t perfect in the relationship.

But now I want to be faithful. I do. I want to change. I’m totally in love with her and I want to marry her and I want her to be the mother of my children and I want to be the man that I always wanted to be. I never imagined myself cheating on my wife, and
I don’t plan on doing that. And I haven’t cheated on her since we’ve gotten engaged. It’s a chance at a fresh start, and I feel like I can live with myself if I change now. If I can stay faithful all the way up until we’re married, I imagine it’ll get easier in time. I hope I don’t get resentful or anything, but so far I haven’t.

I want to start a family, and I think that this is the best setup for a family. And she wants to be married. I mean, yeah, a lot of it is what people expect—people expect you to eventually get married. But it’s also what I want, even if the monogamy aspect of it is not necessarily ideal for me. I don’t think I could have a family and be with other women. It wouldn’t be fair to my children to put them at risk. Kids lose—everyone loses—when you’re unfaithful.

But how does someone who craves something new all the time ever live in this traditional situation of monogamy? How can someone with that feeling ever be married? It sucks. It fucking sucks. And I swear to God, cheating is part of what makes me me. It’s weird to try to kill that off, because I feel like it keeps me sane. I worry that I’ll wither and die when I let that part of myself go. But I love my fiancée to the point where I hopefully can.

I don’t know. I honestly don’t know. I wouldn’t have proposed if I hadn’t felt like, “Okay, I’ve done enough of this.” I’m going to try damn hard to not do it. Or if it’s something I can’t live without, then I have to find a way to do it openly and honestly. I’d have to figure out a better setup than discreetly cheating—I don’t plan on doing that anymore. If I can get past this, I think we can be happy and we will work. I feel very confident that we are going to have a beautiful life together. 

*This article originally appeared in the July 29, 2013 issue of New York Magazine.