The Extreme Lengths People Go to Cheat on Their Partners

"I was shit at being a drug dealer, but having a burner phone made it incredibly easy to text other women without being found out."

by Nilu Zia; photos by Chloe Orefice
Sep 20 2017, 3:40pm

Like murder, cheating on your partner can happen in the third, second, or first degree. At one end of the scale is kissing a random who you pretend didn't happen, and on the other is pre-meditated, cold-blooded adultery. These people go to extreme lengths to deceive: second phones, second homes, second wives, hotel reservations made under fake names, infidelities that are less an accidental inebriated fumble and more a determined effort to be an unfaithful piece of shit.

We spoke to some of these little pieces of shit below. Names have obviously been changed. Except for one. We aren't telling you which.

Roberto, 25

I constantly cheated on my girlfriend in college, from about a month into the relationship. We were together on and off for about four years. We lived in the same hall, and I would bump into her regularly, so I would have to make up excuses for where I was going. A convenience when it comes to cheating as a student means that if all else fails, you can always pretend that you're going to the library, and that's what I would do when I was just going to different halls. The girl I was fucking lived with two of my girlfriend's friends, but for some reason, no one suspected anything suspicious, or maybe they knew what was happening and just never told her. One time, I did actually go to the library, but that was to fuck the other girl in the fifth-floor bathroom. Once, one of my friends was away for the weekend and let me use his apartment. We stayed there from Thursday night to Monday night just fucking and eating Domino's pizza and watching Breaking Bad. I told my girlfriend I'd gone home to visit my parents for the weekend.

My girlfriend never found out about any of it, as far as I know. We're no longer together, but we're still pretty good friends. If she ever finds out, it will be so bad. I also drunkenly fucked one of her friends at some point during our relationship, and I'm more scared she will find out about that, to be honest. I feel like a bad person, but the other girl's vagina was tight as fuck, and I still loved my girlfriend. I was just a horny little dickhead and wanted to fuck everything that moved.

Bry, 29

There was a (particularly) messy time in my life where I was caught between two boyfriends—one was my ex and the other was the next. Unfortunately, the relationship with the next was long-distance and complicated, and my relationship with the ex offered incredible mind-blowing sex on demand—something that any woman can tell you is hard to let go of.

With the next, we started off just having sex in his car, eventually progressing to sneaking him into my room when my housemates were at work, with the thrill that comes with the possibility of being caught making the sex even hotter. He had to leave out the window a few times. After a few months of this, we decided to go away for the weekend so we could just fuck without having to worry about interruptions for 48 hours. I bought us a hotel getaway on Groupon and told my housemates that I was going to stay at my parents for the weekend. My boyfriend never found out, but I eventually came clean to him myself—he didn't really give a shit, to be honest, which I guess is pretty cool? Or not, depending on wether you're into jealousy.

"She asked if I could stay for a minute and help her move stuff back into her room. I did, and the next thing I knew she was completely naked."

Thanos, 26

I was at a house party with my now ex-girlfriend. The girl who was hosting the party was being really nice to me and my girlfriend all night and was saying she wanted to hang out with us again, so at some point we exchanged numbers. I was low-key infatuated with her and thought she might be on it too, but I was with my girlfriend and eventually, we left to go back to her place around 3 AM. I couldn't stop thinking about fucking the other girl and eventually decided to tell my girlfriend that I'd forgotten something important at the party and was going to go back to get it. I called her up, and she said everyone was still partying and that it was cool for me to come back around, but when I arrived, the only people there were her and one of our mutual friends.

We were all pretty drunk and high, and there was still booze and drugs floating around, so the three of us continued partying. A couple of hours went by, and before I knew it, it was 7 AM. The third person had just left, and I was about to get ready to head back to my girlfriend's with my tail between my legs when she asked if I could stay for a minute and help her move stuff back into her room. I did, and the next thing I knew she was completely naked. One thing led to another, and we had sex several times. I stayed at her place until late the next afternoon. When my girlfriend tried getting hold of me, I told her that I'd decided to crash at a friend's house around the corner from the party because I'd missed the bus and no Ubers wanted to pick me up. She believed me and never found out any different. I do and I don't regret it—I was in a shitty, loveless relationship, but I still shouldn't have done it, and I should have at the very least told her the truth afterward.

Jane, 23

When I was in college, one of the girls I lived with was cheating on her boyfriend back home with not one but two of the guys that lived with us. It was so messy, and everyone felt so awkward every time he'd come up to stay with her—everyone apart from the guy she was cheating with, who didn't seem to feel any kind of way at all. She'd make all these elaborate excuses for why she couldn't see him on the weekends—mostly blaming deadlines— and he just accepted it. It was a bit obvious their relationship wasn't going to last and eventually; it all blew up in her face when her boyfriend came around for a surprise visit. She'd told him she couldn't come down to see him for the weekend because she was sick, so he came up to cheer her up and found her in bed with one of the other guys. They broke up, and she started going out with the guy she'd been caught with. I have no idea how the other guy felt about it, but he was a sideman to a sideman, so that's life really.

G, 31

A couple of years ago, when I was unemployed, I decided to try my hand at being a small-time dealer. I was smoking a lot of weed, and I had a bike to get around on. I thought it wouldn't be too much of a stretch from my normal life. I soon realized I was fucking shit at selling weed, but I also realized that having a burner made it incredibly easy to text other women without being found out. I was living with my girlfriend at the time, who used to go through my texts regularly, but for some reason, she never bothered checking the burner, assuming it was for my shitty weed business that she didn't support and tried to ignore. I started sneaking out to see this other girl a lot; she would buzz me on the burner asking for a Q, which meant she was home alone—oh, she had a boyfriend too. I'd tell my girlfriend I was going out to do a couple drops, then go fuck this other girl and come back. I think we kept it up for a good six months before my girlfriend realized I was making absolutely no money from my "business." She put two and two together and kicked me out. I deserved it.