I Tried Speed-Dating On Valentine’s Day — After 40 Bad Dates, Here’s What I Learned

Cristiana Caruso

“Valentine’s Day-themed speed dating? That just sounds sad,” a passerby remarks at the chalkboard signage, as I prepare to *checks notes*... attend a Valentine’s Day-themed speed dating event. So, that was truly the confidence boost I needed before walking into a bar full of over 80 strangers, half of whom I would have to spend three minutes conversing with.

I turn to my best friend Pamela, who is accompanying me because A.) we’d just finished watching the Ted Bundy documentary and she didn’t want me going alone, and B.) she was curious about having 40 first dates in an evening, as well.

“Are you ready to do this?” I ask.

“Yeah screw it, let’s do the damn thing," Pamela says.

The Crompton Ale House in Manhattan is full of dark wood accents, vintage books glued to their shelves, and single people ready to rub elbows on a Saturday night. There are no red and pink decorations, no cheesy indication of what the event was marketed as. I sigh, relieved by the low-key atmosphere.

Pamela and I are directed to the back of the bar, where the good people of NY Minute Dating gave us our name tags and pieces of paper to record the people we met. The next day, we will be able to log onto the website and select the names of the dates we felt we had a genuine connection with. If they selected us back, we will be sent their contact info to continue the conversation. Tinder from the Days of Yore, if you will. Tonight’s event was set up specifically for straight people, however in my search of speed dating events in Manhattan, I found several companies that are geared specifically towards the LGBTQ+ community, such as Queer Speed Dating.

Cristiana Caruso

Before the event begins, I catch up with Amy Van Doran, the CEO and Founder of the matchmaking service Modern Love Club to prepare myself for the evening. “Online isn’t doing well," she tells me in a phone interview. "People are craving, real connections and experiences. People want to be a little more local. Speed dating is brilliant. Online dating works for some people, but the basis of it is chemistry. You can’t read charisma online.” Her advice for anyone looking to get the most of their experience is simple, but poignant, “Treat it like you’re meeting new people, not new potential mates. Be open and friendly and curious and not focus on the end goal of it all.” And so I painted on my best, “I’m having fun!”, smile and hoped for a happy ending or a silver lining, whichever came first.

The hosts explain the rules to the crowd of us while the normal activity of the bar eavesdrops with curiosity: Each date is three minutes long. They’ll ring a bell when that time is up. From there, guys will shift to the seat to their right for the next date. Ladies remain seated. My best friend turns to me, “Well, at least we don’t have to move. So that’s a good start?” There’s something very freeing about getting to sit in the same spot with my glass of red wine and have a parade of men shuffle around to meet me.

While I didn’t know the rest of the people I’d be sharing an evening with, I could only gather that they had the same downtrodden feelings about this time of year that I did. We were all here speed dating, right? I remembered standing in front of the Valentine's Day display at Target in early January nauseated, angry, but also hungry for heart-shaped Sour Patch kids. In my jeans pocket, my Bumble was full of gross messages, my Hinge was devoid of anything promising, and my DMs were drier than Death Valley. Staring me down was a red and pink reminder that for the next month, I felt worthless to capitalist America, just sad and single, ready to buy all the clearance chocolate on Feb. 15. I felt starved of a basic human connection, of something more real than a “u up?” text or an overpriced polyester bear holding a heart.

My Bumble was full of gross messages, my Hinge was devoid of anything promising, and my DMs were drier than Death Valley.

I want some beautiful rom-com moment to fall out of the bright blue sky and usher me into deep conversation. I want to be Cher in Moonstruck, Ginnifer Goodwin in He’s Just Not That Into You, Katherine Heigl in, like, 90 percent of her movies. I want something worth rushing through an airport for, something you want to scream from the rooftops. At the very least, I want someone to keep a conversation with, past the daily, pointless exchanges of the same, “How are you?,” “Good, how are you?” If I could meet more people in an evening than I ever would out in the wild (read: bars), my chances of finding a genuine and organic connection seemed to skyrocket significantly.

Cristiana Caruso

The host rings the bell to commence the evening, and it reminds me of the cannons from the beginning of The Hunger Games. May the odds be ever in my favor. The first person I speak to is an IT manager from Brooklyn with sweaty hands and a kind smile. He asks the standard questions: where are you from? what do you do? do you enjoy your career? Just as I was beginning to hear about the perils of managing a company’s computer network, the bell rings and we have to part ways. While the three minutes were nondescript and barren of any traditional type of spark, it was refreshing to have a natural conversation with someone without the weight of any “we both swiped to get here” expectation.

My third date of the evening is very blunt. He’s an accountant from Queens and spends the majority of our conversation letting me know how much he makes and how it is more than enough money to comfortably support a family. He asks me when I want to have kids and I nearly spit out my glass of happy hour cabernet. “Um, well, probably not for a while. I haven’t really timelined that part of my life yet.” He’s visibly frustrated with my answer, twisting his face into a scowl, responding with, “By the time you’re 35, you’re not going to be fertile. That’s going to be a high-risk pregnancy.”

I wasn’t expecting to find true love tonight, but I also wasn’t anticipating having my biological clock front and center either. Since an open palm slap would probably be frowned upon and may or may not result in Pamela needing to bail me out from a significantly more inviting holding cell, I put on my best resting b*tch face and nodded for the remainder of our time. I didn’t shake his hand when it was time to switch.

Cristiana Caruso

I noticed an interesting pattern for the night. Some men cut right to the chase and either asked me to marry them. Others, noting Valentine's Day looming just a few days ahead, asked very casually what I was doing on the 14th. About an hour into the event, the host announces there will be a 10-minute break for food. People beeline to the platters of snacks, and I turn to Pamela, eyes wide.

“Is this a new low for me? Should I just skip years of online dating and guys named Chad and just join a convent already?” I rub my temples, thinking about how I already wear all black and have minimum contact with men, so pivoting to being a nun wouldn’t be that much of a stretch for me.

“I’m losing my voice,” she squeaks out, “I’ve never talked about myself so much in my life.”

“I’m just winging it at this point,” I confess. “I’ve made up so many hobbies. Am I really this boring? I told the last two guys you were my sister.”

“Oh my gosh, no, you didn’t. I’m telling everyone that now.”

Cristiana Caruso

The bells goes off again. The evening resumes. Pamela squeezes my hand. We can do this. After a date that felt the need to speak to me all but three inches away from my face, I began to wonder what my 50-yard dash time would be in the pair of gold Lauren Conrad heels that I had donned for the occasion. A rolled ankle would be significantly less painful and easier to deal with whatever was ahead of me for the next hour.

Was the whole thing pointless? Was I better off aimlessly swiping, hoping that out of 100 matches, I could find one decent person to Snapchat for a week before forgetting about them? Did I overestimate the novelty of meeting someone in person before getting to know them? I kept a fresh slate with every guy who happened upon the chair in front of me and found myself marking a tiny “X” next to their name as that dollar store bell shooed them away. There would be no cheesy rom-com moment for me tonight.

While my expectations were razor thin at best, as to not hype myself up too much, I wasn’t prepared to not like a single guy I met at the event. Maybe I was the problem? Was I trapped in a giant Taylor Swift song, or perhaps a 24-year episode of Punk’d? Everyone seemed to be at a completely different place in life. The majority of men attending the event were in their mid to late 30s, looking for something serious, and fast. The fastest I’ve ever moved was running away from the bouquet toss at my cousin’s wedding. If I was a different version of myself, set in my career and ready for another chapter of my life, this event would be ideal. But I could barely match my socks or commit to a Netflix show. The 25-year old Titanic-floppy-hair-Leonardo DiCaprio-doppelgänger I’d hoped to meet here was nowhere to be found. Instead, I was surrounded by people who wanted less fun, spontaneous adventures and more settling down and mortgage payments.

One of my last dates for the night was a Ph.D candidate and way out of my age range, but our conversation was cordial enough that I didn’t want to rip all of my skin off. He motioned to my best friend, “So you sister told me that you’re a journalist. I really see the resemblance in you two.” I hold back a chuckle and take the compliment like a free sample at Costco: not enough to satisfy me, but just the right amount to keep me going. I’d come down to Manhattan from Westchester to find a Valentine, a person I could spend time with, but in reality, she’s the one who drove me here.

My rom-com moment began from the second we set out on this adventure. I don't need anyone else’s love but my own and that of the girl sitting next to me, who blocked out her weekend to make sure I wasn’t a news headline.

When we step out into the cold New York City air, I don’t feel the heavy disenchantment that I was anticipating. Instead, I’m overcome with laughter, empathy, and happiness reserved exclusively for babies and women in skin care commercials.

“I owe you for basically ever,” I nudge Pamela.

“Nah, it gives us a good story to tell,” she says as we hustle down the pavement. “Plus...that’s what friends do. They do dumb sh*t with you so you don’t do dumb sh*t alone.”

Cristiana Caruso

It felt good to take a stroll along the edge of my comfort zone, to throw convention to the wind and soak in some good ole-fashioned human contact for two and a half hours. I was certainly more confident in myself to function like a normal person on any upcoming dates I could have. But it felt better to get in the car with my best friend and scream out old punk rock songs from our youth.

I didn’t need to speed through to the part in the romantic comedy where the guy meets the girl, and their eyes lock, and fireworks go off, and the preconceived notion of love being the singular thing that completes you is shoved down our throats. I was perfectly fine with forever living in the first seven minutes, where the lead character and her best friend commiserate about their love woes with Chinese food and reality TV shows. The rest will fall into place eventually, and hell or Hinge, the right guy will show. But having someone in my life to mercilessly interrogate him for me when he does? That’s worth more than a thousand boy-and-girl-ride-off-into-the-sunset-moments.