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. Then he took my hand and asked me to dance. We sat on the same side of the table, our knees almost touching, and we faced each other. He teased me for being from Manhattan and drinking cocktails, and I teased him for being from Chicago and drinking beer.
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. But when the clients joined us, we got back to business.Īfter they left, Justin closed out the tab, turned to me, and asked if I wanted to go to a blues bar. We talked more about relationships and what qualities we liked in the opposite sex. Then he said his last girlfriend turned out to be kind of a homebody and he wanted someone who was more outgoing and fun. 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.Īfter one drink, he asked me was if I still talked to my ex-boyfriend. When we got to the rooftop bar he'd chosen for the upcoming meetings, the sun was setting and the weather was beautiful. I didn't understand why he wanted to go so early, but of course I was up for spending more time with him. 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. We had a client event planned for my first night in the city. 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. It felt like seeing someone I had gone on a date with again. He gave me a hug, and I was a little nervous. When I arrived at the Chicago office, I got off the elevator and walked into Justin's office.
Before I left, my roommate said, "You know you can't hook up with him." And I responded with, "Duh! I know that!" Though we didn't text on the weekends or even follow each other on social media, our relationship was instantly friendly.Ībout 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. And then I remembered that he had girlfriend.ĭuring 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. Maybe it was the wine or the personal conversation, but I could feel a connection between us. 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. 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. Then he casually mentioned that he had a girlfriend, and I thought, "Of course he has a girlfriend." Right after we ordered the next bottle, he got up to go to the bathroom, and I realized that I was pretty tipsy.Īs 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. 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. 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. "Wouldn't that suck not to have sex?" I was taken aback, so I changed the subject. He said, "Yeah, some of my friends got married so they could have sex," Justin said. 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. Granted, in sales, there's a lot of social drinking at work functions, so I didn't think too much of it.
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