What I Learned From Sleeping With My Boss | Men's Health Magazine Australia

What I Learned From Sleeping With My Boss

When I started my job as an account executive in advertising sales, I was 23 and had been living in New York City for a year. I’d also broken up with my boyfriend of six years two months earlier, and I hadn’t been on a date since.

On the first day, my boss, Justin (not his real name), came up to me to say hi while I was setting up my voicemail. I was immediately struck by how much cuter he was in person than via Skype (we’d only done video interviews up until that point since he was based in the company’s Chicago office). Justin was 27, tall, dark-haired, and blue-eyed. Though I would have to be blind not to notice how attractive he was, I told myself he was off-limits since he was my boss.

During our first in-person conversation, Justin told me that the two of us would be going to a “get to know each other” dinner that night. It made sense since we’d be in contact via phone or e-mail pretty much every day. When we got to the dimly lit seafood restaurant he picked, I couldn’t help but notice that it looked like a perfect date-night spot—and then he ordered a bottle of wine for us the moment we sat down.

Granted, in sales, there’s a lot of social drinking at work functions, so I didn’t think too much of it. We started chatting about our industry and my new job, and then, toward the end of the bottle, we got onto the subject of how our friends from the small towns we grew up in got married at a young age—and how neither of us saw our lives going that way. He said, “Yeah, some of my friends got married so they could have sex,” Justin said. “Wouldn’t that suck not to have sex?” I was taken aback, so I changed the subject.

Shortly afterward, Justin said, “So, uh, should we order a second bottle?” He seemed to know he was suggesting something a little taboo because he said it quietly out of the side of his mouth. Even though two bottles of wine at a work meeting seemed aggressive to me, I agreed because I didn’t want to turn down my boss, and I was really enjoying the first intimate conversation I’d had with a guy since breaking up with my boyfriend. Right after we ordered the next bottle, he got up to go to the bathroom, and I realized that I was pretty tipsy.

RELATED: ‘I Slept With My Boss – Here’s What It Was Like’

As we worked on the second bottle, we started talking about what dating is like in a big city, and I told him that I had recently broken up with my boyfriend. Then he casually mentioned that he had a girlfriend, and I thought, “Of course he has a girlfriend.”

I think if there were a larger age gap between the two of us, it would have felt weird to be drinking so much and getting so personal—but since he’s only four years older than me, the line between boss and friend became blurry very quickly.

When I got home that night, I told my roommates that I felt like I had just had a great first date—with my boss. Maybe it was the wine or the personal conversation, but I could feel a connection between us. And then I remembered that he had girlfriend.

During my first weeks on the job, Justin and I talked via instant message and on the phone about his brother getting married, my sister moving to New York, and other details I wouldn’t normally discuss with just any old coworker. Though we didn’t text on the weekends or even follow each other on social media, our relationship was instantly friendly.

About a month after I’d started my job, the company sent me to Chicago for a week to help Justin entertain our Midwest clients at various dinners and happy hours; it was going to be a lot of socializing and drinking. Before I left, my roommate said, “You know you can’t hook up with him.” And I responded with, “Duh! I know that!”

When I arrived at the Chicago office, I got off the elevator and walked into Justin’s office. He gave me a hug, and I was a little nervous. It felt like seeing someone I had gone on a date with again. He and I started setting up my desk, and within two minutes of our hug, he said, “Yeah, my girlfriend and I broke up.” I said I was sorry to hear that and that breakups are tough.

RELATED: Here’s How Many Women Fantasise About Their Co-Worker

We had a client event planned for my first night in the city. But a couple of hours before we were supposed to meet them, Justin suggested we head to the bar early to hang out before they got there. I didn’t understand why he wanted to go so early, but of course I was up for spending more time with him. When we got to the rooftop bar he’d chosen for the upcoming meetings, the sun was setting and the weather was beautiful. The waitress came over to us, and he ordered cocktails for us both—despite the fact that we normally wait for clients to arrive to order drinks.

After one drink, he asked me was if I still talked to my ex-boyfriend. I said I didn’t. Then he said his last girlfriend turned out to be kind of a homebody and he wanted someone who was more outgoing and fun. We talked more about relationships and what qualities we liked in the opposite sex. But when the clients joined us, we got back to business.

RELATED: Spendthrift or Tightarse: What Do Women Prefer

After they left, Justin closed out the tab, turned to me, and asked if I wanted to go to a blues bar. I happen to love blues music and thought, “Another thing we have in common!” When we got there, he went to the bar, got us drinks, and sat down next to me at a big banquet table. He teased me for being from Manhattan and drinking cocktails, and I teased him for being from Chicago and drinking beer. We sat on the same side of the table, our knees almost touching, and we faced each other. Then he took my hand and asked me to dance. I didn’t hesitate at all. While we were dancing, he pulled me closer and said, “This might be inappropriate, but I want to go home with you.” I didn’t feel like, “Oh, my sleazy boss thinks I’m hot.” In that moment, I lost track of the fact that he was my superior.

I knew in the back of my head that maybe this wasn’t a good idea, but we were clearly attracted to each other, so I just went with my gut. I said, “That is inappropriate, but yes.” And we went back to my hotel room.

That was the first time that I had slept with anyone since breaking up with my boyfriend, and the sex was really good—even better than it had been with my ex at the end of our relationship, when sleeping together kind of felt like a chore. In fact, sleeping with Justin felt so great that I stopped worrying about whether I was making a mistake—at least for a little while.

The next morning, we woke up, and Justin tried to cuddle with me. That’s when I thought, “Why are we doing this?” It felt too intimate, and I was concerned about how a relationship might affect our work. So while in bed, we had a conversation about how we wanted to keep things professional in the office. We both agreed not to make it awkward. In my mind, it was a one-time thing, despite the fact that I kind of liked him.

A few days later, we had back-to-back client meetings during the day. Nothing was awkward between us, but the whole time I kept thinking about how we had another client event that night. I was looking forward to it because, deep down, I hoped to spend more out-of-office time with Justin. Also, I knew we would end up hooking up because we’d had so much fun the first time; there was no reason why it wouldn’t happen again. It felt like the beginning of a new relationship, when you just want to spend as much time together as you can.

That night, we took the clients to dinner, then a sports bar. After we said goodbye to them, Justin asked if I wanted another drink, so we got another round. Although I don’t remember what we said, I do remember that Justin scooted his chair closer to mine, and we tried each other’s drinks. While we were talking, he brushed his hand against my leg. I leaned in closer, and he put his arm around my chair. After I don’t know how much time, the bartender said, “We’re doing last call.” Justin said, “Let’s get out of here.” We linked arms, walked out the door, and jumped in a cab. He gave his address to the driver.

Surprisingly, seeing Justin’s apartment wasn’t that weird. I felt like I was seeing my friend’s place; his roommate was there and everything. When I woke up the next morning, I thought, “That was really dumb, but this was the last time.” 

Looking back, I see that I kept making the same decision and regretting it, but it kept happening because I just really liked spending time with Justin. When we were together, we would get so caught up in talking that we would lose all sense of boundaries. Hooking up with your boss sounds bad on paper, but there was an electricity between us that I couldn’t deny. 

RELATED: ‘I Work As A Male Escort. Here’s What I’ve Learned’

When I got back to New York, I told my roommate, “Oh, my gosh, I did it. I slept with my boss.” She said that she wasn’t that surprised because of how I’d talked about him leading into my trip to Chicago.

At work, there was no flirtation, texting, or even talk about what had happened back in Chicago. I liked being able to put it out of my mind like it had never happened; it made it easier to forget that I felt something for Justin. 

About six months after my first trip to Chicago, I went back for more meetings and a work holiday party with 800 clients and other people in the ad sales industry. After the party, I went with a group of clients to another bar, not realizing that more people from the party would be there.

That’s when I ran into Justin for the first time that night. We caught up on all the clients and industry people we’d chatted with up until that point, and he introduced me to more clients from Chicago. As people started leaving, a few of us stayed to dance. My boss and I started inching closer to each other on the dance floor, and at one point he grabbed my hand and twirled me. Then, he said, “My house is actually right down the block.” I said, “I’ll come over!” I had completely given up on my ability to say no to him.

When I woke up at 9:30 the next morning, I was in a serious panic because Justin’s boss had called both of our phones while we were asleep. We were supposed to be in the office to take a group of clients out to lunch. Plus, later that night, I had a flight to catch back to New York. Somehow, even though we were both hungover, we pulled ourselves together and made it to our appointment. Afterward, Justin said, “You should push back your flight so we can go out together tonight.”

I felt too sick to get on the plane, but I didn’t want him to think that it was okay for us to keep hanging out outside of work, so I didn’t tell him I was taking a later flight. But he must have found out somehow because that night he texted me and said, “Hey, I’m playing darts at the bar—do you want to come play?” I said, “I’m really tired and don’t want to go out tonight, but thanks.” And he replied, “Oh, that’s lame.”

I was a little worried that Justin would be upset because I turned him down and then take it out on me at work. Luckily, he acted again as if nothing had happened in Chicago. A week after my trip, he ended up coming to the New York office for another company holiday party.

Although we didn’t talk much at the party, Justin sought me out to tell me that large group of people from work were going to another bar to get drinks. Even though we were with about 20 people, Justin ordered me a drink and chatted with me about work. A little bit later, he told me that a smaller group was going to another bar and asked me to come. As our coworkers started to go home one by one, he became more touchy-feely and started grabbing my waist. He began teasing me for not coming out in Chicago, and somehow I ended up on his lap. Then, after all of our coworkers had left, we started making out at the bar.

I assumed that we would hook up again, though we never had in New York before. When it was getting late, I suggested that we go. That’s when he said, “I’m not coming over. There’s a girl waiting for me in my hotel room.”

RELATED: What High-End Escorts Can Teach A Married Man

The next morning, when I’d had time to process what had happened, I was mad because Justin had blatantly told me he was about to hook up with someone else—right after making out with me. When he revealed that he had another option waiting for him at his hotel—apparently one he preferred—I was furious at him for disrespecting me like that. I was also mad at myself for developing feelings for my boss.

I knew I had to let it go so that I could keep my cool at work, though. So I texted Justin and said that leading me on until 4:30 in the morning was not okay. He responded, “I have the sense that there are feelings here, and you never said you had them. I’m a little caught off-guard.” I used work as an excuse to cover up the fact that he was right. I said, “Regardless of whether there were feelings, you’re my boss, and you can’t pull stuff like that on me.” He said, “I respect you. I don’t know why you would think otherwise.” He asked if I wanted to talk about it to clear the air, and I said, “No, it’s fine. This has to end.” He said, “I think the best thing for us to do is to not partake in that activity anymore.” I agreed.

When Justin went back to Chicago, our relationship turned much more professional than it had been before. Instead of talking about our families and weekend plans, we just talked about two things: work and the weather.

Three months after the girl-in-his-hotel-room incident, I found out that my boss had had a new girlfriend since the Christmas party in Chicago. I discovered this in one of the worst ways possible, too: In a meeting, some coworkers casually mentioned my boss’s girlfriend. I said, “Wait, he has a girlfriend?!” No one at work realised we were hooking up, but they knew we talked almost every day, so it didn’t seem weird that I was surprised he hadn’t told me. One of my colleagues said, “Yeah, she used to work here.” Since the woman lives in New York, I assume it’s the same person who was waiting for him that night.

RELATED: Research Reveals The Top Ten Places For Sex On Holidays

I wanted to confront Justin about having a girlfriend over the phone, but I didn’t want to make a scene at work or give him a chance to defend himself by calling him on his cell. So a week later, when I was scheduled to have a closed-door meeting with him over the phone, I said, “So I heard you have a girlfriend. How long have you been dating?” He started stuttering and said, “I’m not keeping a formal calendar or anything. Why are you asking me this? I’m blushing.” I could tell he was really flustered, so I turned the conversation back to work. I just wanted him to know that I knew—I had nothing else to say about it.

A few minutes later, he instant messaged me and said, “You came in pretty hot with calling me out.” I think he was worried that I was going to tell someone that we had hooked up. Or who knows—maybe he actually felt bad about it. I said, “It’s fine. Just relax. It’s not the end of the world; you just needed to get called out on that.” And he said, “That’s fair.”

Though Justin is still my boss, it can be hard to work together because of our past. I respect him less as a person, but I don’t feel like I need to run away from my job because of it, either. We just keep our conversations short and to-the-point.

Despite how things turned out, if I could go back in time, I think I would make the same decisions. We had a lot of fun while it lasted, and most importantly, the experience prepared me to start dating again. That was the first time in six years that I had been attracted to and had a connection with someone other than my ex.

In the future, I probably won’t be so open to sleeping with another superior because I know that my situation could have turned out a lot worse than it did (no one at work ever found out about us). At the same time, though, I’m open to the possibility of finding love at work. So I wouldn’t rule it out altogether. Plus, the whole thing does make for a pretty great story.

This article originally appeared on Women’s Health Mag

More From