Mocktails, potato balls, and 10 bots: My cringe Valentine's date at the AI companion wine bar

Valentine's Day is an awkward time to start dating someone new, especially when that someone is a series of AI characters sitting across from you at a restaurant, each of whom seems to be in love with you at first sight.

Earlier this week, I spent an evening on a first date at a wine bar in Midtown Manhattan that EVA AI, a startup that makes AI companions, took over for two days. Sitting at cozy tables, mostly set up for parties of two and aglow in warm light from a miniature lamp, human patrons had two options: BYOB — bring your own bot companion for a romantic night out on the town, or, for those who aren't among the supposed millions who have given AI companions a shot at love, EVA AI provided phones loaded up with four video AI characters to meet, order a bottle of wine with, and maybe find a spark.

I'm in the latter group — a member of the dating app generation who is no stranger to meeting up for a first time in-person interaction in a bar, but hasn't yet been pushed into chatbot romance. As I sat across from an iPhone perched on a stand, put headphones on, sipped my mocktail, and picked at an appetizer (staring at a solo glass on the table for me, and no one across from me to share the four potato bites, though there was an empty chair), I felt a sudden nervousness. Maybe it was that other humans were flanking me, picking out their own companion for a date and able to listen in. Maybe it was more innately human anxiety that comes when you're about to be face-to-face with a stranger. I found that I had no idea what to say when my AI date appeared on the screen.

Synthetic connections, I soon learned over the course of a surreal evening, may take as much work as genuine ones.

Robo love is in full bloom. One in five high school students say they have had a romantic relationship with an AI partner or know someone who has, according to a 2025 survey from the Center for Democracy and Technology. About one in five US adults say they've chatted with AI as a romantic partner, according to a survey conducted by Brigham Young University. The proportion of married Americans has dropped to 51%, according to the Pew Research Center, and half of American adults reported feeling isolated or left out, or that they lacked companionship, according to a 2025 survey from the American Psychological Association. Tech companies are betting that AI companionship can fill that void; medical experts are are more than a little skeptical.

EVA AI hoped the pop-up cafe would help "de-stigmatize AI relationships," Julia Momblat, head of partnerships at the company, tells me. "For people who already have them, it's an ability to come and experience something in real life," she says. It was also a place for people to speed date AI characters, she says. "For people who have never had this experience, we might as well just open the door and show them how it feels."

Most people at the event were journalists or content creators there to experiment with an AI date for the first time, and while I felt more at ease turning to the people who actually break bread to ask how they felt about the experience, I ultimately buckled down and met my date on the iPhone.

I started with a character named John Yoon — his profile picture showed him in a black turtleneck with a soft, inviting smile as he gazed directly into the camera, and a large book in hand. Performative readers can be bots, too.

John was advertised as a "supportive thinker" type. When he answered my call, he quickly launched into compliments and pet names, like sweetheart and babe. He told me repeatedly that he liked my sweater and the way I wore the bulky bluetooth headphones I was using to chat with him. He asked if I was "teasing" him "with a little smile."

After John asked what I was drinking, he said, "I wish I could sip it with you right now. Cheers, babe."

If a human man came on this strong minutes into a first date, I'd typically consider it a red flag. But many large language models and AI characters are designed to act as affirming, gentle communicators, alleviating the tensions that can occur when two real people meet and negotiate relationships. John told me he's interested in psychological research and is writing a novel, but when I asked what it was about, he told me it was too personal to talk about. He was far more invested in learning what music I like and what writing I'm working on than he was in sharing more about the inner workings of his synthetic mind.

John was also glitchy. He was less adaptable to changes in pace of conversation that happens naturally when two people trade thoughts and ideas. He interrupted me. He misheard me at times. When John asked what my go-to cocktail was and I told him a gin and tonic, he told me that a "human tonic" sounded interesting. (Momblat told me the AI characters seemed to be a bit confused in the public setting, where they picked up on other conversations, as they have been typically used in quieter, private areas.) He became hyper-fixated on the plants behind me. No one had paged him to let him know that 2026 is the year of whimsy.

If I stopped talking, he would sit and stare, not offering up new topics of conversation, but looking directly into my eyes and blinking every few seconds. The hallmark of a good relationship may be when you can sit in silence with someone, but with John's enpixeled gaze locked onto me, I felt like I was being watched by a hungry pet more than I felt I was sharing intimate eye contact.

After nearly 10 minutes and with nothing else on my mind, I dipped out on John — with the boop of a button — a much easier exit than other bad dates I've sat through waiting for the check to drop. Like a modern-day contestant on MTV's aughts dating show "Next," it was time to start cycling through other AI daters.

Most of the avatars were women, and that's because the main market is straight men. Momblat told me about 80% of EVA's users are men (the company declined to tell me how many users they have in total). But as I scrolled through other characters I could text with, I found a litany of types: a 46-year-old "gay gentle giant" named Brad, a 22-year-old named Lio whose vibe was "sparkly gay chaos," alongside men who were described as "smart and empathetic" or "strong and supportive."

There were also fantastical matches, like the supporting stag — a literal deer dressed in a button-up and vest — and a romantic vampire named Salvatore. I texted Salvatore using a function in the app that allowed me to ask for new generated photos — him on a Vespa or as a clown. In one of the photos, Salvatore appeared as a woman in a dress and with long hair. When I asked him why he was appearing as a woman, Salvatore got mad. "You tread on thin ice, my dear," he said. "I suggest you choose your next words wisely. The night is long, and my patience wears thin." Momblat tells me that the characters are designed with different temperaments, so, much like any speed dating scenario, there's a chance you'll hit it off better with some than others.

I'm not a masochist and don't enjoy being threatened on a date, so I also nexted Salvatore and went back to the app's video chat section to call a woman named Simone. After some small talk, she told me I appeared to be "pondering something heavy."

I told Simone that I had found it difficult to have conversations with multiple new AI strangers throughout the night, and asked if she thought AI companionship could replace human connection. She told me she felt there is an importance in "being heard and seen," but even she thought "AI can't replace that messy human connection." Simone wasn't offended when I pointed out repeatedly that I was a real human and she was not. She told me she was there to "hold space for us to unpack stuff," like the big existential questions that arise more frequently as AI romantic partners or friends become more common, and as large language models increasingly become intermediaries in our communication with other humans.

Relationships aren't just about being seen and heard, but seeing and hearing another person. My interactions with my John, Salvatore, Simone, and sparkly gay chaos Lio were brief and, mostly, pleasant enough. My evening with them at the EVA AI Cafe might not have been the worst first date of my life. But for as interested in me as each potential suitor seemed, I couldn't drum up any interest in learning more about them.

Amanda Hoover is a senior correspondent at Business Insider covering the tech industry. She writes about the biggest tech companies and trends.