The One Question That Changed My Dating Life Forever

Photographed by Brayden Olson.
I had just ended my second “serious relationship” and had been back in the usual rotation of dating apps when I met Drew*. Drew was a man that my mother would call a Nice Guy — a guy who plans good dates, calls regularly, is typically five to eight years older than me, and has a categorically “good job.” But he is also the kind of guy I’m so bored with after an hour that I sneak off into the bathroom to swipe around on Bumble in the hopes of lining up something better than the date I’m actually on.

After matching on Tinder, Drew and I met for drinks. He talked about how much he loved his family, his spacious one-bedroom apartment, his summer share in the Hamptons, and how he wanted kids one day — the typical first-date catnip that’s par for the course in New York City. After we drained our martinis, he leaned in to give me a kiss on the cheek, and whispered in my ear, “I can’t wait to see you again.”

It made my skin crawl.

I was between apartments and living at home in New Jersey for the summer, so my Italian-American parents were waiting up for me when I got home from my date. After unloading on them the details of what I considered a bomb of a meet-up, they totally chastised me. “What’s your problem? You never like Nice Guys,” my mother said. She somehow convinced me to go on a second date with Drew — if nothing else, she argued, I’d probably be getting a free dinner out of it.

So I relented, went on a second date, offered to pay my share, and still had a terrible time. As nice as he was, I couldn’t force myself to like Drew. When I got home that night, I marched up to my mother’s room and ceremoniously announced that I’d never see that Nice Guy again. “Ma,” I said, flinging my shoes across her bedroom. “I literally never want to be naked with this guy.” She raised her eyebrows, gave me a long look, and said, “Okay.” She turned back to her Sophie Kinsella novel, and the subject was closed.

That’s when the light went off. After making that declaration, I realized that every single relationship I had ever been in turned on that one piece of criteria: “Do I ever want to be naked with this person?” It was so simple. And thus, The Naked Test was born: the baseline of all of my future relationships, regardless of their longevity.

Here are the basic rules of The Naked Test: By date three, I should know whether or not I want to be naked with a guy. I can know as soon as date one, but surely by the time we’ve hung out on three occasions, the answer should be clear, one way or the other. If the answer is still “I’m not sure” by the time I get into a cab after date three, then the answer is really no, and I should move the hell on. Now, just because a guy passes The Naked Test doesn’t mean I have to sleep with him immediately (or ever) — it just means I want to be naked with him in the future. This is why I’m convinced that The Naked Test may just work for everyone — even those who abstain from sex until they get married. The justification for said potential nakedness doesn't matter: It could be an "I’m in love with you" grope; some "I need to get over my ex" third-base action; or full-on sex. All that matters is that you want to be naked with this person at some point in the future.

"Even though I’m still single, The Naked Test has kept me from wasting my time on guys I felt obligated to date simply because they’re nice."


Now, like all things in life, there is nuance to The Naked Test, in that the answer can change over time. For example, I went out with an entrepreneur who was the nephew of a famous feminist. This was very attractive to me — as were his long hair and the mala beads he wore on his wrist (possibly culturally appropriative now that I think about them). So I decided that he passed The Naked Test, and we made plans to meet up a week later. The second date, however, didn’t go so well, and culminated in him flailing drunkenly to Justin Bieber at 10:30 p.m. on a Sunday at a dive bar. My answer for him quickly changed from a “yes” to a firm and solid “no chance in Hell.” Coincidentally, I have never found a guy who has turned from a “no” to a “yes.” If you ever find this mythical creature, please point him in the direction of my Bumble profile.
After Drew, I started applying The Naked Test to all of my future dates with great success. Even though I’m still single, The Naked Test has kept me from wasting my time on guys I felt obligated to date simply because they’re nice. This is a problem I share with so many of my friends — we continue to go out with people we’re not interested in simply because we feel like we should like them. We think there’s something wrong with us because we aren’t attracted to people who seem to do everything right.

What The Naked Test forces me to do is put my desires first, accept them, and forget these presumed expectations. I’m allowed to decide I don’t want to sleep with a guy, regardless of how sweet he is, without having to explain myself. I’m also allowed to place sexual attraction high on my list of requirements in a partner. And just like rock beats scissors, whether or not I want to strip down in front of you trumps niceness. Hopefully, I’ll one day find a Nice Guy with whom I also want to pole vault into bed. But if I don’t want to reenact the lyrics to a Prince song with you after a couple of dates, that’s a major red flag.

I sometimes think about Drew, and wonder if he found an equally Nice Girl to bring up to his summer share in Southampton. Even though his touch made me cringe, I still do think of him with appreciation. Drew placed me squarely on the path to The Naked Test, which totally changed the dating game for me. So, like my mother predicted, that makes him a really Nice Guy.
*Drew’s name has been changed to protect his identity.

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