The risky business of dating your lady boss! Dating your lady boss could get you into a heap of trouble, but why worry about it now?
She hired him. She could fire him. But why let such minor details get in the way of a hot romance? One guy’s adventure in dating up.
When it comes to women, I’ve never done anything remotely ballsy in my life. Until 6 years ago, when I flew in the face of everything that Michael Douglas and Demi Moore taught us in the movie Disclosure: I put the moves on my boss.
It all started when I was at the job interview. Maybe because she was cute, maybe because she was funny — or maybe because I was seriously light-headed from inhaling exhaust fumes at the bus station — but somewhere between discussing health benefits and 401(k) plans, I found myself falling for her. I know, I know; it was crazy. What was I thinking? Well for one thing, I was thinking that she was pretty damn good-looking. When the interview ended, a friend of mine who already worked there walked with me out of the building. I turned to her and said, “So, what’s the deal with Lisa*?” (*Note: No names have been changed. There are no innocents to protect in this story.) My friend looked me dead in the eye and said, “Bova, don’t even think about it. She is totally out of your league.”
I took that advice — for the first few months, anyway. Then I got to know her better and realized she was a really sweet, funny person. And after a short time working together, I started to think that maybe we could be more than coworkers. We laughed at the same stuff in meetings, talked about the same stupid TV shows in the mornings. Why the hell not? I mean, yes, she was way out of my league. She was smarter, more successful, and, I assumed, didn’t live in a crappy apartment with a gassy roommate and a cardboard box that served as a dinner table like I did. But what did all of that matter? Wasn’t romance about more than what kind of car you drove (or, in my case, what subway line you rode)? I decided to go for it, and the hard-core flirting commenced posthaste.
Whenever the office went out for a night of boozing, I’d find myself tap dancing, performing magic tricks, basically making an ass of myself to get the boss lady’s attention. Sometimes she smiled. Sometimes (and this is a direct quote) she told me I was “annoying.” But eventually it paid off.
About a year after we started working together, I finally made some serious headway. She had just bought an apartment, so I asked her if she could share some advice on navigating New York City’s treacherous real estate waters. She wrote me an e-mail saying, “Sure. Want to talk about it at lunch? Or drinks?” Holy Jesus, I thought, my cute boss wants to get drinks with me!
So we went out. It was fun. It was a blast…okay, it was incredibly awkward. Should I pay for the drinks even though I make one-tenth of her salary? Would she fire me if I bored her to death? It was a little bit stressful — especially at the end of the night. I walked her to her apartment, and she asked me if I wanted to come up for coffee. We had never clearly established what exactly was going on that night. Was this about real estate?or something more? I panicked. What should I say? “I need to get home to Brooklyn” surely wasn’t what I should have said, but unfortunately that’s what came out of my mouth. (Now do you believe the part about me not being a player?)
Clearly I had blown it — or so I thought. A few playful (read: desperate) e-mails later the next day, we had a second real estate seminar planned. We went out for drinks and in the middle of it, Lisa looked at me and said, “I know this is going to sound weird, but is this a date?” I managed to squeak out a “Yes?” and away our secret workplace romance went.
Sure, it was risky business for both of us — Lisa could have fired me, I could have claimed sexual harassment. If we got busted, she could have lost her professional credibility. But that’s also part of what made it exciting. And though I’d never had a “thing” for authority figures, I have to admit it added to the thrill.
Company policy didn’t officially forbid filling a coworker’s toner after hours, but common sense said it was a bad idea. We worried that our coworkers wouldn’t be able to deal if they found out. The thing was that we had no problem compartmentalizing our dual lives. At work what she said went; after work I had equal authority in deciding between Chinese and Thai. And the more we dated, the more the potential consequences seemed worth it. The thrill and danger that made our relationship initially exciting was replaced by love. We successfully kept things hush-hush for about 8 months until one day I walked into the office and every head spun in my direction. An intern had spotted us holding hands on the way to brunch over the weekend and blabbed. Damn you unpaid, college-credit-receiving laborers!
People were cool about it once they knew, but I could tell that some wondered if any of their confidential lunchtime bitching had made it to Lisa’s ears. Now that everyone knew about us, she felt self-conscious every time she needed to talk to me about work stuff. By that point our relationship was way more important to both of us than our jobs. So rather than risk any weirdness in the office messing things up outside the office, I found a new job.
Any regrets? Today as we sit in our living room (oh yeah, we’ve been married for 4 years now) playing with our 2-year-old son, Henry (oh yeah, we procreated), I have just one: A $1 million settlement for sexual harassment would have come in handy when Henry heads to college.