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.

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.

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.


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