I Tried the Contra-Dating Trend. Did It Help Me Find Love?

One of the perks of dating in New York is that—especially when you have a bad date—there’s always a plan B. In this case, I was venturing to Brooklyn from the Lower East Side to meet up with ‘Oliver’ (I honestly can’t remember his real name). It was February 2022, and I was finally ready to move on from a COVID situationship that broke my heart. I matched with Oliver on Hinge before a trip to Florida, immediately swiping right when I saw his first picture. He was exactly my type: Timothée Chalamet meets Jake Gyllenhaal. We messaged while I was on vacation—I liked that he played guitar—and the next thing I knew I was calling a $35 Uber to meet him in Williamsburg.

When I walk into this comedy club-meets-dive-bar, I’m greeted by a bartender who's dressed like a cast member of The Outsiders. Wearing a silk midi skirt with Prada mules, I stuck out like an uptight thumb. (Lesson learned: Facetime Mom *after* the date). By the time Oliver showed up 30 minutes later, I was off my game. He was even cuter in person—messy hair, dimples, button-down over a band T-shirt—and he had that casual, relaxed vibe I’m drawn to. So of course, I babbled nervously, trying to overcompensate for the loose jeans and Converse I wished I’d worn. Ironically, I accomplished the opposite effect: It felt like I was interviewing the star of the lacrosse team for an internship at his uncle’s company. I remember thinking, Is he uninterested or is he just generally apathetic? After another beer and zero questions asked on his part, I chalked it up to the fact that I simply wasn’t his type. Still, Oliver didn’t miss the opportunity to ask if I wanted to “see” his apartment after I spotted him a $20 for our beers. I didn’t know what he wanted, but I knew that was my cue to take my Pradas back to Manhattan. 

Which brings me to the ‘plan B’ of this story. Before I ordered what was now a $62 Uber home, I wanted to replace the memory of the last two hours with someone else. I immediately pulled up ‘Charlie’ from my contacts, another cool, casual guy who was always around for a drink (never dinner). Charlie and I had fallen into a convenient pattern where we would see each other every few months, usually when one of us felt lonely, both accepting that it would never turn into anything serious. I had my ‘Are you around’ text all teed up when it hit me: Oliver was exactly like Charlie. The two were carbon copies of each other—and it wasn’t just because they dressed like local surfers from Montauk. Both 25-year-olds had a similar, easygoing demeanor that was hard to gauge. I could never tell what they really wanted and the dynamic made me feel insecure—like I didn’t fit the mold of what they were looking for. In fact, I thought, this is exactly how I felt about the COVID guy who took an axe to my heart. 

In that moment, I realized, I was picking the wrong men. Enter: contra-dating.

Perhaps you remember the term Déjà vu-ing, which describes ‘doing the same things with a new partner that you did with your ex.’ It was coined by the dating app Plenty of Fish in 2022, and by no coincidence, I published an article about Déjà vu-ing one week after my date with Oliver. “You might find yourself repeatedly avoiding certain questions because you’re scared to go deeper,” I wrote as an example. “Or maybe, the guy always picks a noisy, distracting bar that doesn’t allow for intimacy.” Both scenarios spoke to patterns I was noticing in my relationships at the time, and two years later, it’s clear that I wasn’t the only single having a dating epiphany. 

In a 2024 report, PositivesDating listed contra-dating as a top trend: “The term is used when you want to broaden your horizon and contradict your usual type,” says PositiveDates relationship coach, Jonathan Hartley. Basically, contra-dating is when you go for someone you wouldn’t usually go for. Hartley explains, “Dating someone who’s not your type may indicate that what you want is not what you necessarily need.” And this is precisely the reason I started contra-dating before it became a trend. I remembered the definition of insanity: doing the same thing over and over and expecting a different result. While I couldn’t help but feel attracted to a chill ski bum, I realized that limiting my dates to ‘that guy’ was the only thing I could change. 

So below, three of my most memorable contra-dates from the past two years. (No real names included.)

As a kid who went to the NYMEX for my Dad’s “bring your kid to work day,” I’m no stranger to the finance bro. The majority of my high school and college friends work in finance, and after four semesters of Wolf of Wall Street-style frat parties, I felt safer with a laid-back stoner. (Even though, to this day, my ‘finance bro’ friends are some of my favorite people.) They’re always energized and motivated—fine, work-obsessed—and fiercely loyal to anyone in their circle. Maybe it’s the New Yorker in me, but I also appreciate that they’re old school: You’ll never open a door or split the bill with a finance guy. 

Enter: Max, 27, a trader at a big bank I should know the name of. I bumped into him on a Saturday in October while bar hopping in West Village. He could’ve been plucked from my friend group—white button-down, dark-wash jeans, Rolex from graduation. And while he wasn’t my physical type, per se, he was far from hard on the eyes. I decided to give him my number before moving on to another bar with friends. 

Right off the bat, I was impressed by this guy’s texting timeline. Unlike those before him, Max was eager to set and plan a date. By Monday night, we had reservations (for dinner!) on Thursday at a buzzy new restaurant in Tribeca. I was used to a last-minute, “Wanna meet for a drink” text after work. Unfortunately, however, Max was just as hands-on during the actual date. Before the waiter could return with the first round of martinis, he had his palm on my lower back. Truth be told, I could’ve left right then and there. But he was amusing and it wasn’t my first time at the rodeo. I slapped his hand away like I would with the frat boys, and he took it as a challenge. Just like the social chair of Sigma Ep, he didn’t realize (or care) that I was genuinely uninterested. 

For the next two hours, Max spoke in tangents between courses. During appetizers, I learned about his future plans, including a beach house in Nantucket and two to three kids. During the main course, he regaled me with tales of ‘epic’ travel abroad and frat parties that will go down in history. By the time the check came around, I felt like the $36 pasta dish was compensation for my time. Overall though, I have to admit, Max was funny and I actually found his stories to be entertaining. It was also the first time I felt I could truly sit back and relax on a date—I certainly wasn’t worried about over-talking. It didn’t lead to a second date but that didn’t stop him from ferociously trying to see me again. 

After a fun but intellectually unstimulating date with Max, I decided to prioritize common interests. I wanted someone creative and artistic—maybe older—who could teach me about the world. This is what led me to match with Harrison, 31, a writer from Bushwick. This time, however, I wouldn’t make the mistake of venturing to Brooklyn. If Max taught me anything, it was that a guy will always make time to see you when he’s interested (bonus for pre-planned reservations). 

Harrison was the total opposite of Max, somewhat closer to my type, but took the ‘laid back’ look to an extreme. We eventually met downtown on a Wednesday after work—and I wasn’t expecting a full-blown beard with Birkenstocks when I walked into happy hour. Regardless, I wanted to keep an open mind, and I was quickly impressed by how present Harrison was. He was eager to know everything about me, and by everything, I mean questions like, “What does love represent to you?” and “What is your biggest regret?”

Initially, this seemed like a good thing. I had grown so accustomed to surface-level conversations about work and sports that it felt nice to sink my teeth into a more philosophical man. But as one drink turned into two, it became clear that something was…missing with Harrison. He was a great listener, looking to delve into the deeper meaning of life, but I didn’t feel a spark with him that would prompt me to call friends on the taxi ride home. Absurdly, talking to Harrison actually made me reconsider Max? Sure, he was a heathen who tried to sleep with me before he knew my last name, but there was something nice about feeling wanted with Max. The conversation with Harrison felt sterile, almost clinical, with no romantic undertone. 

By the end of the date, I found that I was more interested in the idea of Harrison than the person sitting across from me. We had so much to talk about, and while I appreciated his listening skills, the chemistry wasn’t there. Somehow, all of the intellectualizing turned into a lack of intimacy—I didn’t feel connected to him in the way I thought I would.  In any case, I hope Harrison publishes the novel he was working on at the time, and I’ll take his relationship insights to the grave.

Out of respect for this man, I won’t get into specifics. The most important takeaway is that this contra-date led to a relationship that ended. But I will say this: The relationship guy was kind and smart, we’re still on good terms and not once did he ask me to split the bill.

After multiple contra-dates, one of which led to a relationship, I’d call myself cautiously converted. On one hand, it showed me just how low I set my expectations for men of a certain breed. Small things like making reservations and asking insightful questions translated to initiative and curiosity—qualities that were missing from my previous relationships. On the flip side, however, I learned that you can’t force two mismatched puzzle pieces to fit. Even if he looks good on paper, or in an Armani suit, chemistry is something you can’t quite control. 

Nonetheless, this experience made me view ‘my type’ through a more three-dimensional lens. Maybe the guy for me hates surfing and the Grateful Dead—so long as he always makes time to see me. I also recognized that no amount of dimples or hair product felt worth waiting around for (whether that was physically at a bar or emotionally in conversation). In the end, ‘my type’ became someone who could show up for me in the way I needed him to. 

The bottom line: It’s OK to be physically attracted to a certain kind of guy…so long as you give other types a fighting chance. With that mentality, a contra-date can be a useful jolt to the system. It forces you to get out of your comfort zone and really think about what you’re looking for from a partner. Worse comes to worst, you leave with some entertaining frat stories to share with your girlfriends over cocktails.