Sex Lives: The Guy Who Was Hooking Up With His Olive Garden Coworkers

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Sex Lives chronicles the evolution of one person’s sexual history. This week: Hank, 35, in Key Largo.

My first time was most certainly memorable. Some of it was awesome, and some of it was a little confusing. It was the first time for both of us, which made things worse, but it also helped us mentally understand that the other person didn’t know what they were doing either. It happened in my dorm room at Mizzou a few months into my freshman year. We lasted for two and a half hours, and she came twice. I didn’t come at all, which is maybe not a typical first-time experience.

We were in the middle of a relationship; we dated for about two years. I think we started having sex six or nine months after we started dating, and we were together for another year and a half after that. I think we did pretty well together, albeit I’m now recognizing that there was still much to be desired. Our sex at that point was very, very vanilla. We didn’t experience a lot of different positions or anything like that; what we did worked well for us then. It helps when you’re 18, 19, 20, you’re both very physically fit—everyone’s arguably the most attractive they’ll ever be. At that stage, it was everything that I could have hoped for.

After we broke up for the next year, it was kind of back and forth between us. I think we either didn’t know what we wanted or wanted multiple things. We were both too young and immature to understand how to handle the situation and when to stop doing what we were doing. That year, I remember having sex several times—even after she had started dating somebody else, we would still hook up occasionally. I hated it, absolutely hated it. I was the one on the cheating side of things, but it still felt like she was cheating on me with the other guy. It was the worst of both worlds. I was guilty because I was the one cheating, and I felt super awful because I felt like I was being cheated on all at the same time.

We finally got strong enough to stop reaching out to the other person as we had been that year. Sometimes, we would see each other every day. Sometimes, there would be a month in between. And then one of us would call the other or send a drunk text or something, and all of a sudden, we’re back in the what-the-hell-are-we-doing phase. Eventually, it just happened that neither one of us did that anymore. A big thing that helped was that I moved to Alaska for a seasonal job about six months after we stopped dating. Distance helped.

I started dating somebody when I moved to Alaska; we were only together for about six months, and she was a rebound. That sounds harsh to say; she was a fantastic person. I enjoyed my time with her, and she definitely helped my mental health and helped me recover from the previous breakup. But at the same time, it was probably not the best thing for me to do to her because I was never as committed to the relationship in the same way that she was. There wasn’t any cheating or anything like that. I just always saw an endpoint where she was looking for more than that. But it helped me out. There were a couple of random hookups in between before her. So, I think she was the fourth person I slept with, but I was her first.

If the first experience for me—with my first girlfriend—was pretty great, this one was awful. It was the worst-case scenario you can imagine for a woman having sex for the first time—tons of crying. I’m having an awful time. I kept asking in the middle of sex, “Do you want me to stop? Do you want me to stop? This is not working.” And through the tears, she would say, “No, keep going.” It was a horrible experience. The sex got better as the relationship went on, but the first time was terrible. After my seasonal job ended, she moved to Seattle, and I moved to Denver to be in AmeriCorps. The relationship lasted maybe two months after we moved apart. We were in no shape to have a long-distance relationship.

It always seems that I find hookups if I’m looking for a relationship. If I’m looking for hookups, I find a relationship. That’s been a strong theme throughout my adult life. The year I was in AmeriCorps, what I wanted—at least, what I thought I wanted—was to find “The One” to find the next long-term relationship. But I was in a new state every two months for the job, and that constant moving around made it pretty much impossible (not that I saw it at the time). You’ll never have a long-term relationship when you must be gone in a month and a half.

One hookup happened the day before the girl I saw in Alaska, and I broke up. I did it kind of out of spite because I was positive that she would break up with me. I don’t think she’d called me in a week or something like that. I was angry and assumed a breakup was coming, so I hooked up with somebody. I ended up being right, and the next day, the girl from Alaska called me and, without knowing any of it, broke up with me. Not one of my finest moments.

There was a bar across the street from the campus where we lived, where all the AmeriCorps people would go because they wouldn’t card if you were 19 or 20. So we could all be together, hang out, drink, and have fun. There were a number of hookups that started there and then led to sex back in the dorm rooms. On the last day of the job, I think everybody was kind of sad that this experience was over for us, and everybody was saying goodbye and kind of looking for physical comfort, so I know a lot of people hooked up with other people at that point; I ended up doing the same thing.

The AmeriCorps program I was part of was about 500 people, and we were broken into teams of about a dozen; I never did anything with the people who were directly on my team, but when we were back at home base in Denver, everyone was there together, and we’d all go to that bar. The person I hooked up with on the very last day, well, she was known amongst the group. She played the ukulele and performed at a talent show and a couple of other times. Everybody knew her as the ukulele girl. It’s one of those things where I don’t even know how it happened because I’d never spoken to her, but I remember walking up to her in the bar, saying goodbye, kissing her, and then walking away. And then, at the end of the night, when the bar was closing, she was walking around looking for me. I couldn’t tell you why I acted that way besides alcohol and emotions, but it ended up in sex.

I moved back to Columbia, Missouri, intending to return to school. I didn’t initially, but I got a job as a server at the Olive Garden. And that place… that place changed my life in a lot of ways. For a few years after that, I lived what I would consider a pretty standard “restaurant life.” Everybody’s partying, everybody’s hooking up with each other, and then you show up to work still drunk the next day—plenty of hookups.

Then, I started dating somebody in 2012; that was the most serious relationship I’ve had to date, and it lasted five years. To me, the best sex has typically been long-term relationship sex. Maybe it’s planned, maybe it’s not. You’re probably doing the same two or three positions in the same order because you both know what works, and you’re both comfortable with each other, and it just makes sense. So, that five-year relationship is probably what I would consider the best sex because of those things. Of course, we had the super horny sex where you’d get blindfolds and gags and all kinds of stuff like that, but the best sex was just the regular relationship sex.

After five years, she believed that I was never going to propose. That was another reason why we ended up splitting up. I had a proposal plan in place when she broke up with me. We broke up in March; her birthday was at the end of June. I had a plan for her birthday weekend; I had a ring picked out and the plan in place. The next step would’ve been to meet with her parents and siblings and purchase the ring.

I’m a pretty introverted person. I’m not shy, but I’m introverted. I need alone time. I tend to keep to myself. I’m not loud or anything like that. But sometimes, during sex, it feels incredible to be allowed to be very dominant, like choking and tying people up and stuff like that. I never thought I’d enjoy that until I tried it. All three girls I was in a relationship with mentioned that they might be interested in various forms of that. Usually, it started with bondage and spiraled from there. I didn’t really get into it until the third girlfriend— the one where we were together for five years. I think experiencing those things combined with the comfort and safety of a long-term relationship allowed me to realize how much I enjoy being dominant. It’s not a necessary part of every sexual experience by any means, but sometimes it’s pretty awesome.

I’ve been seeing somebody for a few months, but it’s likely over. I’m not sure, honestly; I should probably ask. It’s eerily similar to why my last relationship ended—my schedule is the same. I work evenings in a restaurant, and her schedule is the same as my ex’s. She works Monday through Friday during the day. She’s 41 and has three kids, and obviously, that takes up a significant amount of her time. Understandably so. She’s from the area, and her siblings, cousins, parents, and grandparents all live within a 10-minute drive. They’re a typical Cuban family, and everyone’s very close with each other, and they will always be a priority when your time is limited. It’s difficult to break into someone’s life.

Originally Appeared on GQ