sideguy2

Confessions of a Side Dude

What it’s like to be the other man — or manstress, if you will

Every year on either February 13th or 15th, some men and women come together to observe Valentine’s evil twin: Side Chick Day. While Hallmark has yet to lay claim to the holiday, Urban Dictionary first cites its existence in 2011 (its exact origins remain unknown), a few years after the term “side chick” itself became popularized. 

Side Chick Day is exactly what it sounds like: a day for dudes to celebrate their dirty little secrets, which they tend to have more of than women. (About 20 percent of men admit to cheating compared to 13 percent of women, according to the U.S. General Social Survey.) But as more women have entered the workforce, ladies are closing the “infidelity gap,” giving rise to a strangely sleazy feminist accessory: the Side Dude. 

Who, though, are these Side Dudes? 

In honor of their special day, I spoke to three of such dudes about their very different experiences of being the Other Man, or manstress, if you will. 

‘It’s like getting hired for a job that someone got fired for.’

David, 31, podcast host, Brooklyn: It had been a few years since we broke up, but I knew she had a boyfriend because we were still friends on Facebook. Our communication slowly got more sexual over Snapchat; then one day she was like, “We should fool around again because it was really fun.”

She was getting her needs met emotionally just not physically, so I was just kind of mail-order dick. It never felt like she was trying to rekindle a more meaningful relationship in case hers didn’t work out. If it did, I probably wouldn’t have done it.

I’m poly so I’ve been the side dude before and after that time, but I won’t do it when I personally know the other man involved. That’s when you usually get into “I’m gonna steal your girlfriend” territory. I have a line, and that’s where I draw it. I don’t want to make it seem like I’m some fuck mercenary. I always, too, try to bring up that there are other options than just straight-up cheating, like an open relationship. But me not cheating with them isn’t going to stop them from cheating. They’re going to get it somewhere else. 

Sometimes people cheat because it feels wrong, but for me, it’s more than that. It feels like I’m so desirable that they’re willing to risk their relationship to be with me. It’s a compliment. It’s like getting hired for a job that someone got fired for. 

Being the other man has taught me that women are better at cheating — mostly because the consequences are different. If a guy gets caught cheating, he might lose his relationship, but he probably won’t lose his friends. He may get temporarily canceled by a few female friends, but they usually come back around. Women, on the other hand, get judged way more harshly for it — losing friends, family and sometimes work in the process. It’s easier for women to have sex, and as a society, we get mad about that and make the punishment harsher if they have sex “wrong.” 

Basically, then, if you know the punishment is going to be worse, you become a better thief. 

‘The crazy thing is, I became friends with her husband.’

Philip, 61, actor, Newfoundland: I was performing at a drama festival at the time. A few months earlier, I’d ended a relationship that made me feel like I was finished with relationships. One night I said, as a joke, “I’m not going out with any woman unless she asks me to the beach at night,” because I was pretty sure no one ever would. 

Tess was there in the audience with her sister, just visiting for the weekend, and went to the bar where we were all hanging out after the show. She was very enigmatic to me. So I went over and said hello, and I’ll be damned, she asked if I wanted to go to the beach. 

We got to the beach around one in the morning and talked until the sun came up. She told me right away that she was married and had a daughter. I told her about my failed relationship. We told each other everything because we thought we’d never see each other again. Her marriage was basically dead. They hadn’t been intimate for at least a year, and let’s just say it was an honor to be the guy to fill those needs on the beach that night. 

Afterward, she dropped me off at rehearsal, and I thought that was it. But two weeks later, I had a gig playing guitar at a local bar that I’d briefly told her about. I went early for a sound check and there she was, sitting at the bar. It was the most amazing feeling. 

She’d been there for two days waiting for me to show up and said she’d felt a loss from the moment she dropped me off. That was exactly what was wrong with me for those two weeks, too. It was kismet, and moments between us have been like that ever since. 

I wanted to be more than a secret, but if I’m being honest, I was so vulnerable at the time, I would’ve been fine with just that. But she had so much integrity — she was going to tell her husband whether I pursued her or not. He was upset for a few hours, but by the next day, he came around. She bought a smaller house here for her husband and daughter and found him a better engineering job. Then she moved in with me.

We were together from that point on. The crazy thing is, not long after, I became friends with her husband. It’s nothing too involved or weird. Her daughter took right to me from the moment we met. That had a lot to do with him accepting me, and he’s just a super guy. We actually met on the soccer field; we were all there to watch her play. He eventually remarried, and we’re all very polite. 

Her family, however, disowned her for six months. They’re part of a very Catholic community where you’re not supposed to get divorced. Eventually, though, they made peace with it. They know Tess is a special person. And they know I put her on a pedestal. They could see me serenading her and being romantic all the time. They knew her ex-husband wasn’t doing that for her.

‘One time she told me, “This morning when I was in the mood, I reached over, grabbed my husband and called out your name.”’

Willy, 71, educator/activist, Dallas: I used to love country-western dancing so much that I’d go out by myself to do it. One night when I was around 35, I was dancing at a club called Cowboys. I approached Mary, who was out with her friend Debbie, to ask her to dance. It just took off from there. She asked me if I’d like to come back to Debbie’s house. When we got there, one thing led to another, and nature took its course, so to speak. Then she said to me, “I gotta go, my son and husband are waiting for me at home.” That’s when I found out she lived with her husband down the street from Debbie. It was like, “Oh Jesus!”

We saw each other a few more times after that. One time I was talking to her on the phone, and she told me, “This morning when I was in the mood, I reached over, grabbed my husband and called out your name.”

I was like, “You did what?” 

That’s when we ended it — it was just too risky.

Then there was another woman many years later. Again, I was out country-western dancing. She was a pretty good dancer, and sure enough, we ended up in the backseat of my car. I didn’t think much of it because she wasn’t wearing a wedding ring, but the next day she called me and asked what I was up to. I invited her to my apartment to watch football, but after about two hours she had to go. I was like, “You don’t have to leave, you can stick around longer.” But she just said, “No, the football game is over, and now my husband is going to be looking for me.”

Well, shit, I thought, I did it again. That, though, was the last I ever saw of her. 

A few months later, I met another married woman who was separated from her husband. Every Thursday for three or four months she’d show up at my place. But it turned out that she was just using me for a physical thing. I broke it off because I felt like a piece of meat.

To that end, a big part of being the other man was desperation on my part. I felt like I was going to be alone forever, and I don’t like being alone. I was basically a street kid from the age of 10. My parents were drug addicts and never around. Now these women weren’t exactly barefoot and pregnant — if anything, they were all ambitious career women — but they did have husbands and families. And they chose to put their affairs with me over those husbands and families. That was very attractive to me. 

It also got me over the relationship hump — no pun intended. Because it helped me figure out that I wanted a family, too. Today, I have 33 years invested in my current marriage and a daughter. I’m not going anywhere either.

So looking back, I have no regrets whatsoever.