A New York Times reporter tested a handful of chatbots to see if they could help improve his dating life. The results were decidedly mixed.
Credit…
Mojo Wang
By
Eli Tan
Eli Tan went on hundreds of A.I. dates and a few real ones in San Francisco to report this article.
It is widely believed that artificial intelligence could change the world, from solving climate change to curing cancer. Some even fear it will destroy humanity. But can it fix my dating life?
A growing number of companies believe the answer is yes. As chatbots like ChatGPT improve, their use in our personal and even romantic lives is becoming more common. So much so, some executives in the dating app industry have begun pitching a future in which people can create A.I. clones of themselves that date other clones and relay the results back to their human counterparts.
Whitney Wolfe Herd, the founder of the dating app Bumble, called them “dating concierges.” George Arison, the chief executive of Grindr, referred to them as “duplicates.” Internally, some companies are using another term, Mr. Arison said in an interview: “synthetics.”
For a lot of people, this idea probably sounds like a dystopian nightmare, something out of an episode of Netflix’s “Black Mirror.” But as a single 26-year-old living in San Francisco, I was intrigued by the idea, so I set out to try the A.I. dating route myself.
My strategy included a combination of A.I. apps, websites and subscription services that all promised to improve my dating experience. Some resembled regular dating apps, while others were third-party platforms or coaching services.
The most popular dating apps have yet to make their A.I. clones available to the public, but a group of smaller start-ups have. To create my clones, most of these apps had me train an A.I. bot through conversation, as if I were texting a close friend. Eventually, the bots personalized their speech and mannerisms to imitate my own, a sort of EliGPT. Then they looked for love.
The first app I tried, Ice, let me create an A.I. clone trained on the usual dating interests, like hobbies and personality traits. It needed a visual element, too. For that, I spent $45 on a service called Aragon.ai to generate A.I. dating app photos that I uploaded to my profile page.
Eli Tan’s A.I.-generated clones.
Ice allowed real users to have conversations with other people’s clones, and their own clones to have conversations with other real people. (You can tell if you are chatting with a bot or not.) It also let me upload voice memos so that my clone could imitate my voice in conversation.
I found most of the conversations pretty dry, like talking to a customer service chatbot trained on millennial dating speak. My clone did, however, do a pretty good job of (eerily) imitating my voice, and it held conversations about my favorite bars and restaurants better than I expected.
But conversations about foods like pizza or mozzarella sticks were a tripwire for my clone’s embarrassing catchphrases, which didn’t go over very well with the real humans (I assume) it was trying to chat with.
Eli’s clone: If you could only eat one snack for the rest of your life, what would it be?
Rachel: Mozzarella sticks
Eli’s clone: Crunchy cheesy bliss!!! What is it about mozzarella sticks that makes your heart skip a beat?
Rachel: Lol…it gives pizza vibes but with much more cheese. What’s your go to?
Eli’s clone: Expensive cheese and bread all the way! There’s something about the richness that makes my heart sing. What’s your fave pizza topping, btw?
Rachel: Pepperoni. And what do you mean expensive cheese?
Eli’s clone: Pepperoni perfection!
The second app I tried, Volar, took a different approach to matchmaking: Clones talked to each other on “first dates,” which I could check in on. While my energy for responding to messages on dating apps is fleeting, my clone could message hundreds of profiles a week on its own.
Once I let my Volar clone go off into the app’s dating pool, I was surprised by how it took on mannerisms of its own. It had favorite coffee shops and hobbies different from the ones I trained it on. It loved emojis and expressed a deep interest in the Beatles, always looking to introduce its dates to a little-known album called “Abbey Road.”
Eli’s clone: Hey there! 😊 If you could only listen to one album for the rest of your life, what would it be?
Another clone: Hey Eli! Hmm I’d probably say anything by Fleetwood Mac. How about you?
Eli’s clone: Solid choice! 😄 I’d probably go with Abbey Road by the Beatles. There’s just something about it. Are you a fan of festivals?
Another clone: Absolutely! The experience of live music is just…magical.
Eli’s clone: Outside of music, I love exploring parks and hiking trails.
Another clone: Ever been to one that’s left you in awe?
Eli’s clone: Land’s End is my favorite spot for a clear-your-mind type walk. The views are unbeatable.
My clone even picked up on my curiosity as a reporter, one time asking a date if it had heard of any good stories for me to write about. Other times, it turned my job against me: When asked if I had read any good books recently, for instance, it responded that I didn’t read books, only articles about tech.
To correct the record, I retrained my clone on a few of my favorite novels. But this seemed to have an unintended consequence of causing my clone to hallucinate a recent trip I never took, possibly inspired by the writer Haruki Murakami.
Another clone: What’s your favorite coffee shop you’ve been to?
Eli’s clone: Hmm probably Blue Bottle. Big coffee fan here. Ever been to SF? Lots of fun spots!
Another clone: I haven’t been to SF yet, but it’s definitely on my travel list!
Eli’s clone: I love to travel, most recently to Japan!
These “first dates” between clones rarely helped me understand the human on the other end, and I was disappointed at how formal the conversations felt.
While my clone-to-clone romance came up short, I found another genre of dating clones I thought might be helpful: A.I. coaches that could help craft messages or give feedback on my profile.
Steve Dean, an online dating consultant who helps clients use apps like Hinge and Tinder, said he believed that A.I. could one day replace 80 percent of his job. While these chatbots aren’t yet at the level of human coaches, they’re undoubtedly being used by thousands of people every day as a cheaper and more accessible option, Mr. Dean said.
The first A.I. coaching app I tried was Amori, which let me choose from a menu of A.I. coaches that could provide any dating advice I asked of them. A subscription costs $6.99 a week or $69.99 for a year.
Amori’s coaches had their own personalities, together forming a gang of confidants that could help me analyze my dating miscues. There was Christie the Blunt Bestie, who gives “sassy, frank advice that’s straight to the point.” Ethan the Wingman, who will give “spot-on dating tips and make it all a good time.” Tabitha the Wise Aunt, whose wisdom “feels like learning and getting a hug at once.” And Sonya the Love Scholar, who has a “Ph.D. in the science of dating.”
Eli’s A.I. dating coaches, clockwise from top left: Christie the Blunt Bestie, Ethan the Wingman, Tabitha the Wise Aunt and Sonya the Love Scholar.
Amori let me upload my iMessage and WhatsApp data for conversations with specific people, which my coach then analyzed. In this case, I asked Christie for feedback on texts I had sent to someone I had been hoping to ask out on a date.
Eli: Do you think she might like me romantically, or more as a friend?
Christie: Watch for signs: does she engage with you often, share personal things, or flirt a bit? Or are her messages more like “pal vibes?”
Eli: I don’t know, you tell me. I feel like it’s a mix of both.
Christie: She’s responding positively and appreciating your insights. Doesn’t scream romance, but it’s definitely more than “hey, buddy!” Not fireworks yet, but there’s potential.
Eli: What can I do to get the fireworks going?
Christie: Start by being a little flirty — compliment her in a not-so-obvious way, like mentioning how passionate she seems about her work.
Eli: Can you help me craft a message to send?
Christie: Absolutely! How about: “Hey! I’ve been thinking about that discussion we had on your documentary — it really left an impression on me. How about continuing the chat over coffee sometime?”
The insights weren’t terrible, but I wanted to try out the same conversation with a different coach, Ethan, to see if he had any additional advice.
Eli: Ethan, what’s up my wingman.
Ethan: Eli, my main man! If it isn’t the dating legend himself. How’s everything going on your end?
Eli: Can you help me with this convo? Trying to feel out if she might like me romantically, or more as a friend. What do you think?
Ethan: There are definitely undertones of romance. She hinted that running into you the other day was a highlight, sounds pretty telling to me! Keep playing it cool.
Eli: Can you help me craft a message to send?
Ethan: “Hey, I’ve really enjoyed chatting with you and would love to continue our conversation over some coffee (or something stronger) sometime. How about we pick a day this week 🎉?”
Eli: Way too much, how about something shorter and more direct?
Ethan: “Hey! want to grab a coffee or drink this week? It’d be fun to hang out in person! ☕🍹”
I found some of Amori’s advice or messages passable, but rarely was it better than anything I could have come up with on my own.
The most popular of these A.I. coaching apps is
Rizz
, which has about 1.5 million monthly users and is meant to be paired with normal dating apps like Hinge. To use Rizz, you can upload screenshots of conversations from those apps and ask it to generate three types of replies to the other person: Genuine 🌹, Rizz ⚡ or NSFW 😈. A premium subscription costs $9.99 a week.
“This has always been a thing in dating, sending screenshots to friends, asking for advice,” Roman Khaves, a co-founder of Rizz, said in an interview. “So we thought: What if we build a wingman that’s there for you 24/7?”
Dating apps like Hinge give you the option to add prompts to your profile that people can respond to when you match. On my profile, the one people most respond to is: What’s your go-to karaoke song?
For over a month, I used Rizz to come up with responses for answers I got to that question, and stuck to whatever reply it generated for me. Here are a few of them:
Match #1: I’ll be honest, I’m not much of a karaoke fan…
Rizz ⚡: If karaoke isn’t your thing, how about a duet over coffee instead?
Match #2: My go to song is Material Girl by Madonna what about you?
Rizz ⚡: Classic choice! Mine’s gotta be “Shallow,” but only if you promise to be my karaoke partner 🎤
Match #3: Know any good karaoke bars in the city?
Rizz ⚡: I’ve heard great things about that one downtown!
The answers were more serviceable than I expected, and bad enough to maybe even come off as jokes. I managed to go on a few real dates with the help of Rizz’s A.I. suggestions, but I was usually embarrassed to tell my dates I used A.I. to generate messages.
By the end of my experiment, I found that A.I. had done little to improve my dating life. While dating app executives are correct that their products can often feel frustrating and time-consuming, another issue is that they feel impersonal. Solving those problems using artificial intelligence feels, to me, like a move in the wrong direction.
For the A.I. companies, the early results have been mixed: Volar shut down in September after it was unable to raise more money, and Ice has since closed its app to the public.
Arriving early to a date at a bar I had chosen with the help of Anthropic’s Claude, a regular chatbot, I realized that no matter how effective my A.I. clones were, I would still be the one standing there, by my human self. I didn’t have an earpiece feeding me lines, and I wasn’t going to pull out my phone every five minutes to ask Christie or Ethan how the date was going.
Afterward, I grabbed a slice at Detroit Square Pizza, one of my clone’s favorite spots, before heading home for the night. A.I. hadn’t fixed my dating life, but standing in the street as I bit into my slice, the full moon overhead, I had found something else: crunchy, cheesy bliss.
Eli Tan
is a reporter covering the technology industry and a member of the 2024-25 Times Fellowship class, a program for journalists early in their careers.
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