“How does the idea of being slapped hard in the face during sex make you feel?” a software engineer named Will asked me in a conference room full of our co-workers.
“I think being slapped in the face during sex is the kind of thing you feel out as you get intimate with someone,” Will said, leaning back in his chair. “Do we really need to ask about it?”
“I guess we know what Will likes in bed,” another engineer finally said.
At 23, I’d worked at OkCupid for two years and was used to talking frankly about sex in the office. But did Will like getting slapped in the face? I buried my gaze in a spreadsheet, avoiding his eyes. I’d hoped I would learn the answer eventually, but not like this.
When I started at OkCupid, fresh out of Princeton with a computer science degree, I thought the literal database of New York City’s single men at my fingertips would help me find a fellow math nerd. Instead I was hung up on the hipster without a high school degree who sat two desks across from me.
I hated this on principle. Even before #MeToo and Silicon Valley’s reckoning with sexual harassment, I considered intra-office dating off-limits. I was one of the only women in the office as well as in my undergraduate computer science classes, and I knew the consequences of a strongly skewed gender ratio: A platonic study session could turn (unrequitedly) sexual at any second. When I asked a classmate to partner with me for a programming competition, I was “giving a signal,” and when I denied it, I was “a total tease.” But this was small potatoes compared to the horrifying stories of stalking and harassment my female engineer friends brought back from the Bay Area. Best to remove romance from the workplace altogether.
Also: Will wasn’t single. Worse still, he’d met his girlfriend on Tinder, our competitor!
I tried to use OkCupid to get over my crush, planning dates with men who were more my “type” — an astrophysics PhD from Columbia, a programmer at Twitter, a graduate student from Cornell who had taught computers to tag the cutest cat photos on Reddit. According to OkCupid, I was highly compatible with them, but I was hung up on Will. Psychologists are skeptical that the qualities we filter for on dating sites — shared interests, personality types — have anything to do with relationship success. But most agree that purely spending a lot of time with someone predicts attraction; the “mere exposure effect,” as it’s known.
Then one day, as I scrolled through OkCupid profiles, I found a guy who caught my eye. He listened to Fleet Foxes, worked at Facebook and listed competitive programming as a hobby. Hot. Something about him felt familiar, but I couldn’t place it. So I messaged him and we chatted for a week until I realized something: I recognized him from a party at Will’s apartment months back.
“You’re Will’s brother!” I messaged in horror.
The next day on coffee break, Will called me out. “My brother is incredible,” he said. “You should absolutely give him a chance.”
I didn’t know if I should take this as a compliment — Will liked me at least enough to introduce me to his gene pool — or as an omen that he wasn’t into me himself. It was tempting, being matched with someone who was ostensibly a clone of Will but who was single, college-educated and whom I didn’t have to see five days a week. But what if something went wrong? Plus, they were roommates.
“Sorry, I don’t mix my work and personal life,” I told his brother coolly.
But that wasn’t true. I worked at a dating company. I knew exactly which of my co-workers were single, because I’d match with them on OkCupid. This was how I learned, late one Sunday when Will’s selfie popped up on my phone, that he liked dad jokes, had insomnia and was newly single.
On Monday, I caught Will in the elevator wearing brown leather shoes and a linen blazer. “Sometimes I wish everyone in tech wasn’t so casual,” he said. “Now whenever I dress up, everyone knows I’m going on a date.”
I still considered Will off-limits, but threats to his singlehood were imminent: At the office lunch table, he’d recount his weekend dates at bars in Red Hook and comic book stores, and kisses with too much teeth.
So I flirted without flirting. I planned “dates” for the entire office — karaoke, camping, drinking, boating — and always sat next to Will, hoping he’d take the hint. But when he got to work in his blue “date jacket,” I knew he wasn’t getting the message.
Then on one rainy evening after work, I caught Will alone walking to the subway. Be cool, I told myself, don’t talk about dating.
“So, dating. Sounds like you’re doing a lot of it!” I said. “What are you looking for?”
“I guess I look at relationships as a window into another person’s life,” he replied. “I like dating people who are completely different from me.”
“Funny!” I said, “I always go out with guys just like me — programmers.”
“Really? ” he asked. “I would never date a programmer.”
Was this a subtle rejection?
As we neared the entrance to the subway stop, he turned to face me and took a breath. “Look,” he said. “I’m going to say this once, and I promise I won’t bug you about it ever again.”
He paused. I looked up at him, so tall he’d have to bend down to kiss me. I wondered what I’d look like in his plaid flannel, what it would be like to spend the night at his Williamsburg apartment.
“I think you should give my brother a chance,” he said.
“Will. I would never, NEVER date your brother.”
“Okay!” he said, stepping back. “Forget I asked.”
Discouraged but persistent, I kept at my old tactic. The next week, I held a board game night at my apartment and invited all my co-workers. At midnight they left, except for Will, who stayed back with a half-full glass of whiskey. “I just want to finish my drink,” he said.
We sat close on my couch. Be cool, I told myself, don’t talk about dating. “I think maybe you should kiss me,” I said.
He looked down at me, still so tall he’d have to bend down to meet my lips. But this time, he did. “I’ve been into you for months,” he said.
“Me, too,” I replied.
“This kind of thing never happens,” he said.
“Yeah, usually when you like someone you don’t tell them about your Tinder dates and say you’d never date someone with their job and try to set them up with your brother,” I said, feeling salty.
Will looked hurt. “I just didn’t want to be one of those guys,” he said. “One of those neckbeard engineers that hits on his coworker — the only girl in the office. I was so afraid of making you uncomfortable.”
“What changed your mind?” I asked.
“When I realized I knew I’d rather quit than not tell you how I felt.”
The next night, I stayed at Will’s apartment. On the way to his bathroom in the morning, I met the programmer brother I’d messaged months ago. “Dale?” He looked surprised. I smiled, glad I’d held out for the original.
There was no explicit policy forbidding employee dating, but Will and I agreed not to tell anyone. The secrecy was kind of hot. We’d ignore each other until the end of the workday. Then I’d slip out of the office 10 minutes early to wait for him in the candle-lit lobby of the Ace Hotel.
After five months, Will quit his job. With nothing left to hide, we came out. “Well, obviously,” a co-worker said. “Why didn’t you just tell us? Nobody would’ve cared.”
He was right — nobody seemed surprised. But then, as now, I still didn’t know: When is it okay to ask out a co-worker? When you were sure the feeling was mutual? How could you ever be? OkCupid statistics show that more than half of users have fanaticized about hooking up with a colleague, and there’s even a workplace dating app for Slack. But I’m still conflicted. When people ask me how we met, I just say: “Through OkCupid.”