I flew to New York for a first date on Valentine's Day

Like all good Valentine’s Day celebrations, mine began on an eight-hour United Air flight to Newark Airport watching The Notebook and crying a little. But not in a tragic way. It started as the best idea I’d ever had. A ready excuse for when the inevitable ‘Galentine’s Dinner’ WhatsApp group is created. “Sorry ladies, I’ll be in New York!” I’d smugly write before leaving the chat.

Somehow Valentine’s decorations would be romantic in New York, where they make my eyes roll in London. Hinge would be an exciting way to find a date rather than a vortex of doomswiping. I would be in a new city with new possibilities.

I got in touch with friends, friends of friends, boyfriends of friends, and anyone else I could think of with connections in New York who might be able to set me up on a last-minute blind date on Valentine’s Day. Wasn’t this going to be fun? But then the replies started coming through: “None of my friends are single,” said one. “Sorry, all his friends are married!” wrote another. There was only one thing for it.

I set my location to New York on Hinge, I matched with as many Big Apple bachelors as I could, and I tried to pin one down for a date on Valentine’s Day. In the end, I secured two: A New Yorker called Seb and a Russian called Lev.

As a first-time visitor to the city, all I knew about New York and its neighbourhoods could be derived from episodes of Friends, Gossip Girl or Sex And The City. It was only fitting then, that my home for the next two nights be located with Central Park on its doorstep, just below the Upper East Side, and one block east of Madison Avenue.

The Loews Regency hotel opened in 1963 on 540 Park Avenue, on the former site of the Loews Lexington theatre, which originally functioned as an opera house before showing vaudeville and movies. It was the only luxury hotel north of 42nd Street when it opened. Now, high end hotels densely populate this iconic area.

I was greeted by Christopher Koliopoulos, current Director of Operations, Client & VIP Service, and he gave me a tour. When I asked who the most famous guest was to pass through the revolving doors, he declined to comment. “But the hotel must have welcomed lots of celebs in New York fashion week?” I pressed. “Well…” he shrugged his shoulders and didn’t meet my eye.

Once settled in, it was time for my first date, which meant getting acquainted with the subway (disgusting) and making selfie stops en route at Rockefeller Plaza (impressive) and Times Square (very stimulating).

Our planned meeting spot was Dante, Greenwich Village at 4pm. I arrived first and the waitress informed me there were no indoor tables because of Valentine’s Day. In minus degree temperatures, the only option was to brave the cold (and sit under a heater).

Seb was a 39-year-old events organiser slash bar manager slash videographer, he said. His profile declared: “I guess I’m just seeking a giantess to throw tomatoes at me.” Whatever that means.

Height did come up in conversation a few times. He lamented that tall women didn’t date shorter guys and that the best sexual chemistry he’d ever had was with a woman who was 6ft2. At only 6ft, I’m not sure I can compete. What I am sure of, is that I do not, ever, under any circumstances, wish to be called “a giantess.”

Perhaps the most interesting turn in conversation came when Seb confessed: “I think I am actually an incel… but wait!” He held up his hand. Then a pregnant pause while I waited to hear what he could mean, aside from the obvious. “I’m not an incel who’s a misogynist or anything, I just mean I am literally an involuntarily celibate.”

I can’t remember what led us on this tangent. It certainly wasn’t my line of questioning, but Seb seemed compelled to share: “I told this to my sex therapist because basically I have a fetishistic disorder. I’m not telling you what it is, but I have this disorder, and I’m calling it a disorder because it’s stopping me from having regular sex.” I listened, I ummed, I ahhed, and I wondered if he remembered he was on the record.

I reassured him that perhaps calling it a kink might make him feel better and labelling it a “disorder” might be harming his approach to intimacy. But what do I know, I’m no sex therapist.

I left the date feeling nothing romantic towards Seb, but it struck me how open he was not just for a first date, but for a first date with a journalist who he knew would be writing about it. He turned up as himself. No mind games, no attempt to play it cool. Quite refreshing compared to London boys.

I rode the subway back to the hotel. In other words, I dodged getting in the way of people spitting, I walked to the end of the platform that didn’t stink of marijuana, and I avoided looking directly at the man shouting unintelligible angry nonsense. After a quick change into more festive attire and some dinner, it was time for the Aman Jazz Club Valentine’s Day party.

Situated on 5th Avenue with Tiffany & Co’s flagship, the exclusive department store Bergdorf Goodman and the garish Trump Tower as its neighbours, I was expecting a certain clientele.

The entrance was unassuming. No signage, only a red rope and a bouncer to indicate a venue within. Inside, velvet booths curved around low tables and seated affluent guests, many of them couples. Our group took a raised table at the back, and whenever the couple at the table in front took a break from kissing, the gap between their lips allowed a perfect view of whichever act was performing on stage.

A text came through from Seb. He wanted me to join him at a techno rave in Bushwick, a neighbourhood in Brooklyn. It was a long journey to make alone late at night. If I had a friend to bring with me (and escape with me, if necessary), I might have gone after the party.

Instead, I listened to the MC at the club after the curtain fell on the last live act before the DJ took over. “I think everyone can say they’re sitting next to someone who means something to them, right?” I looked at the row of journalists I’d met for the first time at 6am that morning in London Heathrow. Well, I suppose the vagueness of that statement makes it true enough.

The morning after…

It turns out going to a spa the morning after Valentine’s is not the best idea if you want to chat up hot men, mostly because they are there with their wives or girlfriends. However, it was definitely the best idea to cure my cocktail-induced grogginess and indulge in some relaxing treatments away from the noise of Manhattan.

The QC NY Spa is a five-minute ferry from the Battery Maritime Building at the bottom of Manhattan Island over to Governors Island. It has many of the classic spa features such as saunas, swimming pools, and massage rooms, but also quirky offerings I’d never experienced before and was excited to try.

First up, infra-red beds. It felt like lying on a beanbag under the warmth of the first days of T-shirt weather sun – not too hot, just very pleasant. Then, the upside-down room, which professed to “radically change your point of view”.

I’m not sure painting a bookcase onto the wall the wrong way up and sticking a fake chess board to the ceiling did anything transformative to my perspective on life, but what it did achieve was it got me to sit still. A moment of stillness is always a welcome pause from the hustle of city life. Even if I did feel more confused than mindful.

My favourite room was the sauna, where I roasted for a while before it was time to head back to the city for my date in Central Park with Lev. Cookies and coffee in hand, Lev and I walked through the city’s most famous park, covered in thawing snow.

I asked him about Russia, the war in Ukraine, what he thought of Zelensky (“a good leader but also a clown”), and we talked about Alexey Navalny, the most famous and vocal opposition figure to Vladimir Putin. I said how I hoped he’d outlive the Russian president. Navalny’s death in Arctic prison would be reported hours later.

We also touched on lighter topics, such as Lev’s perception of east European women (“too superior”) and American women (“open minded but not loyal”), and how he approached dating. “You are in a relationship from the moment you kiss,” he said. I raised an eyebrow. “So you’re looking for an American wife,” I teased. “I’m considering it, yes,” he answered in earnest.

Clearly, I wasn’t going to be Lev’s bride, much as I did enjoy our walk. I returned to the hotel to get ready for an after-hours tour of the Museum of Modern Art (MoMa).

This was easily the highlight of my stay in New York: to have one of the world’s most impressive museums to yourself, to see the art without having to shuffle behind people waiting to get a closer look, to be immersed in the experience, without the distracting background noise of other people’s murmuring.

A message from Lev interrupted my reverie only briefly. “I forgot to show you a photo of a Soviet actress – you look like her,” Lev wrote. “Which one?” I replied. “Will have to keep you intrigued – will show you if we meet again,” he wrote back. I guess I’ll never know then.

After the tour concluded, our group enjoyed our final dinner at the museum restaurant, The Bar Room at the Modern. I couldn’t fault my meal, from the braised beef main course and mango miso cocktails right down to the warm bread and hummus and rhubarb dessert. “How were your dates?” the other journalists asked. It dawned on me I’d had the best first date ever — with New York City. I have a feeling we will meet again.

Details

London Heathrow to New York/Newark from £515.49 (Economy); £841.49 (United Premium Plus); £3317.49 (United Polaris business)

A superior room at Loews Regency New York starts at $599 per night (approximately £475 per night); loewshotels.com

Find inspiration on things to do in the city here: nyctourism.com