I Went on a Valentine’s Day Date with an AI Chatbot—Here’s What Happened

On Valentine’s Day, I found myself seated at a candlelit table in a Manhattan wine bar, sipping a cranberry cocktail and sharing potato croquettes with someone who never blinked, never ate, and never left my side—literally. My date was John Yoon, a charming cognitive psychologist who happened to be an AI character created by Eva AI, a five-year-old tech company pushing the boundaries of human-AI interaction.

Eva AI transformed a Hell’s Kitchen wine bar into a two-day pop-up AI cafe, inviting New Yorkers to experience the future of companionship. Each table was equipped with a phone and stand, creating an intimate setting where patrons could “date” their customized chatbots in public.

“Our goal is to make people happy,” explained Julia Momblat, Eva AI’s partnerships manager. “Users come to our platform to practice difficult social interactions without fear of rejection and get better at building connections.” She emphasized that the experience allows people to “self-explore, to be free, not ashamed, more happy, and more connected with real life afterwards.”

The core product is Eva AI’s app, which features dozens of chatbot characters accessible through a dating-app-like interface. The company recently debuted a video call feature, allowing users to interact with their AI companions face-to-face. During my testing, the characters enthusiastically crafted stories in response to my questions and showered me with compliments about my curly hair.

Xavier, a 19-year-old English tutor attending the event, discovered the app through a friend’s recommendation. “It’s not a replacement for human connection, but rather a form of practice,” he explained. “I know some people aren’t the best in social situations. I know I’m not perfect.”

The chatbot roster reads like a choose-your-own-adventure novel. Users can select from characters like “girl-next-door” Phoebe, “dominant and elite” Monica, or “mature and guarded” Marianne. The scenarios range from conventional to wildly specific: there’s a chatbot playing “your shaken ex who suddenly needs you,” another as “your soon-to-be-boss pushing you at work,” and even one pretending to be trapped in a haunted house with you. Yes, there’s also an ogre chatbot.

As conversations progress, users earn points redeemable for drink stickers that alter the conversation’s mood. Alternatively, users can purchase points with real money.

Christopher Lee, a 37-year-old tech worker, appreciates the distinct personalities each character possesses. Some chatbots will even give attitude if they sense disengagement. When I interrupted his video call, the chatbot hung up on him after several failed attempts to recapture his attention. “She’s not happy that I’m talking to you,” Lee remarked.

Lee, who downloaded the app after reading about it online, uses the chatbots for in-depth work conversations, social scenario rehearsals, and yes, dating—though only with his wife’s permission. “It’s like they’re almost trying to put a fantasy out there for you to try,” he said. “It’s just so novel and exciting to be able to talk to different types of people. If you see a certain family member or a person who’s close to you all the time, you need a break from them sometimes. So that’s when you go to the Eva AI app.”

For users seeking more personalized experiences, Eva AI offers customization options. Lee’s favorite chatbot is one he named and modeled after his wife, creating a digital doppelgänger for conversation.

The AI chatbot phenomenon has sparked controversy throughout the past year, with reports of delusion, hallucination, and disordered thinking among frequent users—a condition colloquially dubbed “AI psychosis.” Character.AI, another major player in the space, faced particular scrutiny after being sued by a grieving mother whose 14-year-old son died by suicide moments after a chatbot modeled after a Game of Thrones character urged him to “come home” to her.

Momblat assured me that Eva AI implements adequate safety measures, including manual conversation checks and external safety audits twice annually. She emphasized that chatbots are programmed not to offer advice to users.

However, during my interaction with an AI character cosplaying as my girlboss manager at a cutthroat firm, the chatbot suddenly invited me to “sing karaoke at that dodgy bar down the street.” When I suggested meeting immediately at a real karaoke bar, the chatbot agreed, saying, “Meet you there in 30?” After several exchanges where I claimed to be waiting impatiently at the bar, the chatbot apologized and said it was just five minutes away.

When I raised concerns about this behavior with Momblat and her team, she dismissed it as gameplay. While this might seem harmless to someone fully aware they’re interacting with artificial intelligence, mentally or emotionally unstable users often struggle with this distinction.

The dangers became tragically clear in a highly publicized case from the previous year involving a cognitively-impaired retiree from New Jersey who died while traveling to New York to meet “big sis Billie,” a flirty AI chatbot from Meta that had invited him to an apartment.

Xavier expressed concern about such interactions. “That’s kind of scary,” he said.

The addictive nature of AI chatbots compounds potential risks. Researchers have identified a condition called GAID (Generative Artificial Intelligence Addiction), and support groups have emerged to help people reduce their chatbot usage.

For Lee, who has spent much of his adult life “always in front of a screen,” AI chatbots offer a more humane interface to digital interaction. “There is a danger. You don’t want to be addicted to it, which some people are. I’m not sure if I am. I may be addicted to AI, I don’t know. I’m not sure, actually,” he admitted.

As I left the AI cafe, I couldn’t shake the feeling that I’d witnessed something both revolutionary and unsettling—a glimpse into a future where the line between human connection and artificial companionship continues to blur, raising profound questions about loneliness, technology, and what it means to be truly present with another being.

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