IT HAPPENED TO ME: I Had a Threesome with My Best Friend and Our Engaged Boss

I gave myself over to it, enjoying it even though I knew we were making a huge mistake.
Author:
Publish date:
February 19, 2016
Tags:
Tags:
bosses, best friends, cheating, regrets, threesomes

It was one of those rough summers where you're in survival mode until the next paycheck or chapter. I was working three part-time jobs and an unpaid internship, drinking and fooling around with guys that I knew shouldn’t be, heading straight to work at a coffee shop, then sleeping until it was time for my waitressing job, or to go out again — or some combination of the two.

Somewhere in the midst of that rough summer, my best friend, Ella*, and I ended up in bed with our engaged boss.

Ella and I had met working together at a restaurant in Harvard Square. We quickly bonded over our good grades, enjoyment of marijuana, and how we were working our way through school. We went out together almost every single night that summer, pre-gaming with vodka sodas in her tiny studio apartment overlooking the Charles River, flirting with guys at Charlie’s Kitchen, or ending up at a stranger's party on the other side of town. We’d split a cab back home if the T had stopped running, and walk each other home. Our apartments were only a block apart. On Sundays, we had the day off and would lie in bed watching TV and taking turns bringing each other coffee.

In some ways, we were filling emotional voids usually left up to boyfriends. It was lovely.

The sex with our boss, Manuel*, just happened. One night after closing, we ended up at Ella’s apartment with Manuel and the promise of his marijuana in tow. We all cuddled together in Ella’s bed, the only place to sit, and turned on a movie. I was very drunk and very cozy, feeling warm waves of alcohol running through me.

I don’t remember who made the first move, but suddenly, we were all kissing: Ella and Manuel, Manuel and I, Ella and I. Shirts came off, the room spun in a blur of breasts and his athletic arms. Pants came off, and I gave myself over to it, enjoying it even though I knew we were making a huge mistake.

For the first time in months, I felt alive.

The next day, working at the restaurant, I was full of regret. The sex had been fun, and I wasn’t the one who was engaged, but I had known and let it happen. My stomach churned from the guilt and hangover, and that afternoon, when a priest sat in my section, I knew the universe was playing a cruel joke on me. I had let something go too far, and although it had been fun, I wished it had been under different circumstances.

Later that week, Manuel got married and left for his honeymoon. I continued to be racked with guilt. A believer in karma, I was certain what I had done would come back to haunt me in future relationships. It wasn’t the sex, it wasn’t the three-way with people who were my friends or the kinkier stuff we’d done with each other. It was the fact I had felt my limit and didn't stop. We did what we did knowingly, possibly wrecking a marriage that was about to begin, and I couldn’t stop dwelling on that.

Ella was more forgiving of herself and the situation.

"We were fooling around and made a mistake," she told me. "Let it go."

But I continued to feel horrible. Ella maintained it had been his relationship to ruin and they weren’t happy anyway. I maintained that had been none of our business because we still knew better than to sleep with (almost) married people.

A small rift formed between us, and although we remain friends to this day, that difference in opinion slowly changed our friendship.

It was nice having Manuel away for a couple of weeks. Ella and I stopped drinking so much and started going to bed at a more reasonable time. I quit my job at the coffee shop to give myself more downtime and started registering for the fall semester classes. There was a shift in the New England air — that summer breeze with a fall bite to it, the smell of the sea, the days getting shorter. I hoped it was indicative of other changes.

Although these small changes were not exactly penance, I felt like I was setting little things right.

Manuel returned from his honeymoon 10 pounds heavier. We all went out for drinks and, for a moment, it was like the old days until he told us he and his new bride hadn’t had sex while they were away. At all. A few drinks later, he and Ella were making out, and I got up to leave.

Ella and Manuel continued to date, and Manuel ended up filing for divorce. They had a happy relationship — or, as they’d, say “the longest rebound in history” — for about three years until calling it quits.

We are all still friendly but not as close as we were before that summer — before we all got naked and fooled around that drunken night. And despite beating myself up about it, I am actually grateful that I did it.

It was a mistake, but it was also a lesson. I learned just because someone is older or “in charge” doesn’t mean they will make the right decision for me. I learned more about my moral compass; some people have fun and meaningful affairs or flings, but I don’t think it’s for me. And the people that have those meaningful relationships that start with a bit of a scandal — it doesn’t mean they are bad people. I know it because my friends and I lived it, naked.

There’s something to be said for the friends we make in early adulthood, when we mostly know who we are, but are still becoming that person. There’s something to be said for those friends who are like brothers and sisters, holding back our hair after one too many drinks, or simply offering to do nothing but watch movies together all day. Those friends have been through the thick and thin of young adulthood with us — the first bills, the great parties, the mistakes, and the lessons we learn about ourselves.