Nice Guys Finish Last

At this rate, someone was bound to get hurt. And it probably wouldn’t be me.

In case you haven’t noticed: I’m super judgmental. People always say this like it’s a bad thing, but I think my skill to make snappy decisions about whether someone is awesome or horrible is something of a super power. This handy trick has made dating very difficult (as you can see), so sometimes, if I can’t specifically pin point what’s wrong with someone, I make an extra special effort to not judge them right away.

This is how I sometimes end up dating “nice” guys with nothing wrong with them per se, but also not a whole lot right with them. Like Jake. Jake is extremely nice. We met on OkCupid, and had our first date at Rye. He was nervous, and I could tell. But it was sort of sweet. We had a few drinks and had a pleasant conversation. It wasn’t necessarily a riveting conversation, but I’d snap judged a lot of guys recently and had decided to make an effort to stop. Anyway, after our second drink, I was ready to head home, see if he ever called me and go from there.

He asked if I wanted another drink.

“No thanks,” I said. “It’s getting kind of late.”

We stayed for another hour after that, sitting with our empty glasses. And not because the conversation suddenly got interesting. The waiter never brought the check. Jake didn’t ask for it. I didn’t want to ask for it. So we just kept making not-very-interesting small talk.

Finally, the check arrived. He didn’t reach for it. Ugh. Had this guy never been on a date before? It was past midnight, and I was dying. Finally, I reached for it, and that’s when he stepped in and grabbed it. Finally.

We walked out. It was pouring rain.

“Let’s walk east,” he said. Seriously? It was practically a monsoon out. But I was not being judgmental, so I pulled on my hood and started to walk. Three blocks later, I’d had enough and hailed myself a cab. An awkward pat on the back later and I was on my way.

When he asked me out again via text the next day, I strongly considered ignoring it. But I decided that his awkward lack of ending our date was due to nerves. And I owed it to this nice guy to give him a second chance.

We went on two more dates. He was equally uncomfortable on them. I won’t bore you with all his little stumbles, which I at first thought were endearing. I’ll just give you the highlight reel.

Date two: We’re on the way home, splitting a cab uptown. We were an awkward distance from each other. Would he kiss me? I didn’t know. I could see him grappling with whether to put his arm around my shoulder. The arm goes up a little, he scratches his chin, back down. Up a little, adjusts his collar, back down. We were three blocks from my apartment when he decided to go for it, but he was a little two eager and BAM—he elbowed me right in the nose. I instantly died laughing. Yes, it hurt, but it was too hilarious for me to focus on the pain. Poor guy was mortified. “I’m so so so sorry,” he muttered. With only a block to spare, he planted an awkward kiss on my swollen face. Poor guy.

Date three: Jake took me to a comedy club. The date idea was great. The date itself was the same “nice” but awkwardness I’d felt on every other date. And Jake was still openly nervous. I knew I didn’t want to see Jake again when, during the show, we literally laughed at the complete opposite jokes. I was peeing my pants over jokes that had him checking his phone—and vice versa. A shared sense of humor is a must for me. At one point, Jake got up from the table to use the bathroom. On the way back, he banged his head on the hanging lamp over our table, sending it toppling and banging onto our table mid-show. He was, once again, mortified.

I didn’t end things with Jake just because he was clumsy. But if by the third date I still made him so nervous it threw off his depth perception, something was very wrong.

—Raz, 26, NYC