When we were together, we would get so caught up in talking that we would lose all sense of boundaries. Then he took my hand and asked me to dance. 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. 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.
When I woke up the next morning, I thought, "That was really dumb, but this was the last time.
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A little bit later, he told me that a smaller group was going to another bar and asked me to come. 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. I happen to love blues music and thought, "Another thing we have in common!
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. That's when I ran into Justin for the first time that night. At work, there was no flirtation, texting, or even talk about what had happened back in Chicago.
In my mind, it was a one-time thing, despite the fact that I kind of liked him. Granted, in sales, there's a lot of social drinking at work functions, so I didn't think too much of it. Then, he said, "My house is actually right down the block.
He and I started setting up my desk, and within two minutes of our hug, he said, "Yeah, my girlfriend and I broke up. Hooking up with your boss sounds bad on paper, but there was an electricity between us that I couldn't deny. 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? 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.
It felt like seeing someone I had gone on a date with again. We talked more about relationships and what qualities we liked in the opposite sex. I felt like I was seeing my friend's place; his roommate was there and everything.
He teased me for being from Manhattan and drinking cocktails, and I teased him for being from Chicago and drinking beer. Then he said his last girlfriend turned out to be kind of a homebody and he wanted someone who was more outgoing and fun. So while in bed, we had a conversation about how we wanted to keep things professional in the office.
As people started leaving, a few of us stayed to dance. Even though we were with about 20 people, Justin ordered me a drink and chatted Sleeping with your married boss me about work. Nothing was awkward between us, but the whole time I kept thinking about how we had another client event that night. We sat on the same side of the table, our knees almost touching, and we faced each other. 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. While we were talking, he brushed his hand against my leg.
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. He gave me a hug, and I was a little nervous. He gave his address to the driver. I'd also broken up with my boyfriend of six years two months earlier, and I hadn't been on a date since. When I woke up at the next morning, I was in a serious panic because Justin's boss had called both of our phones while we were asleep. I know that! We both agreed not to make it awkward. I didn't hesitate at all.
When I started my job as an executive in advertising sales, I was 23 and had been living in New York City for a year. That night, we took the clients to dinner, then a sports bar. Afterward, Justin said, "You should push back your flight so we can go out together tonight. I said, "That is inappropriate, but yes. 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.
It felt like the beginning of a new relationship, when you just want to spend as much time together as you can. 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.
He began teasing me for not coming out in Chicago, and somehow I ended up on his lap. 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. As our coworkers started to go home one by one, he became more touchy-feely and started grabbing my waist. We were supposed to be in the office to take a group of clients out to lunch. That's when I thought, "Why are we doing this? 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.
Looking back, I see that I kept making the Sleeping with your married boss decision and regretting it, but it kept happening because I just really liked spending time with Justin.
But when the clients ed us, we got back to business. 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. Then he casually mentioned that he had a girlfriend, and I thought, "Of course he has a girlfriend.
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. Then, after all of our coworkers had left, we started making out at the bar. Surprisingly, seeing Justin's apartment wasn't that weird. 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.
Though we didn't text on the weekends or even follow each other on social media, our relationship was instantly friendly. Shortly afterward, Justin said, "So, uh, should we order a second bottle? After I don't know how much time, the bartender said, "We're doing last call.
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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. After the party, I went with a group of clients to another bar, not realizing that more people from the party would be there. After one drink, he asked me was if I still talked to my ex-boyfriend. He said, "Yeah, some of my friends got married so they could have sex," Justin said.
I slept with my boss. 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. A week after my trip, he ended up coming to the New York office for another company holiday party.
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When we got to the rooftop bar he'd chosen for the upcoming meetings, the sun was setting and the weather was beautiful. When I arrived at the Chicago office, I got off the elevator and walked into Justin's office. Plus, later that night, I had a flight to catch back to New York.
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. Right after we ordered the next bottle, he got up to go to the bathroom, and I realized that I was pretty tipsy. I said I didn't. After they left, Justin closed out the tab, turned to me, and asked if I wanted to go to a blues bar. I was a little worried that Justin would be upset because I turned him down and then take it out on me at work.
After we said goodbye to them, Justin asked if I wanted another drink, so we got another round. I was looking forward to it because, deep down, I hoped to spend more out-of-office time with Justin. While we were dancing, he pulled me closer and said, "This might be inappropriate, but I want to go home with you. About six months after my first trip to Chicago, I went back for more meetings and a work holiday party with clients and other people in the ad sales industry.
I leaned in closer, and he put his arm around my chair.
On the first day, my boss, Justin not his real namecame up to me to say hi while I was setting up my voic. Somehow, even though we were both hungover, we pulled ourselves together and made it to our appointment. I didn't understand why he wanted to go so early, but of course I was up for spending more time with him. It made sense since we'd be in contact via phone or e-mail pretty much every day. 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. 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.
When I got home that night, I told my roommates that I felt like I had just had a great Sleeping with your married boss date—with my boss. And then I remembered that he had girlfriend. Maybe it was the wine or the personal conversation, but I could feel a connection between us.
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. Justin was 27, tall, dark-haired, and blue-eyed. Before I left, my roommate said, "You know you can't hook up with him.
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.
Luckily, he acted again as if nothing had happened in Chicago. The next morning, we woke up, and Justin tried to cuddle with me.
A few days later, we had back-to-back client meetings during the day. We had a client event planned for my first night in the city.