The rise of the AI wingman

• Daters are using AI to slide into the DMs and craft Hinge profiles.
• Three singles told Business Insider that they had used ChatGPT for pick-up lines, dating app bios, and texting advice.
• A crop of startups are fighting for these AI-powered daters, while dating apps like Tinder and Hinge experiment.

When Rebecca Koltun met a man in the VIP section of a club in Tampa, she didn't ask her friends for advice. She asked ChatGPT.

Should she text him first?

"Chat told me no," said Koltun, a 26-year-old from St. Petersburg, Florida, who works for a ballet nonprofit. "It said that this is a guy in a VIP section. He's used to girls' attention. The best thing to do is leave him alone and wait for him."

A week later, the man texted Koltun. "So chat's advice worked," she told Business Insider.

Koltun is one of the millions of daters using AI as a coach, therapist, and friend. Dating app swipers use chatbots to refine their profiles. DM sliders use AI to generate their pick-up lines. Anxious blind daters use the tech to ask whether they should text the following morning.

Angling for space on daters' homescreens is a growing, mostly bootstrapped startup space. Apps like Rizz and YourMove, once viral hits, are now establishing stable user bases and say they're profitable. Dating app heavyweights, such as Match Group and Bumble, are engaging in talks with these apps, per the startup founders, and developing their own competitive products.

How much should we entrust our dating to AI? TikTok is full of daters convinced that they're Hinge matches are using ChatGPT. There's a whole "South Park" bit about it, and even a new word: "chatfishing." (While catfishes use fake photos or life stories, chatfishes use AI-altered voices.)

Founders and singles alike say that seeking AI's help is the future of dating, whether we like it or not.

Welcome to the era of the AI wingman.

Goodbye, dating coach. Hello, AI.

Chase Dennis, an 18-year-old student from Wyoming, uses ChatGPT to slide into DMs. He asks the chatbot for jokes or rhymes, he said, but then edits its output to stay in his own words.

Do the pickup lines go over well? "It depends on the girl," Dennis said. "Most of them do. Sometimes they just think I'm a cornball."

Dennis said he often tells the recipients that his pickup lines were AI-generated — and that they mostly found it funny. "I've been nervous to tell them because they might think I'm unoriginal, but honestly, I think I'm pretty iconic," he said.

Daters like Dennis are being courted by three cohorts of businesses: startups, dating apps, and LLM makers.

Leading the startup pack is Rizz, founded by Roman Khaves in 2022. The app offers witty replies and compatibility scores based on dating app chat screenshots. Khaves branded it as an AI dating assistant when the space was still in its infancy. "Now, there are hundreds of them," he said.

Rizz has been downloaded by 13 million users since its founding, Khaves said, and has 400,000 monthly active users. The app was profitable from the outset, even before venture capital became interested, he added. Now, when the VCs knock on his door, Khaves said he turns them down.

Racing behind Rizz are companies like YourMove and Roast, founded in 2022 and 2024, respectively. YourMove has "well over" 1 million downloads, per its founder, Dmitri Mirakyan. (Mirakyan no longer manages YourMove as he pursues another startup.) Roast has "millions" of free users, said its cofounder, Benoit Baylin, and close to 100,000 paying users.

Then there are smaller apps that have grown their audiences. There's Wingman (4,700 paying customers), FireTexts (10,000 installs a month), and Amori, one of the few VC-backed startups in the space (10,000 registered users).

These startups are mostly oriented around dating apps and DM slides, though they can also be used for flirty messages far beyond a first date.

Who's using these apps? It's hard to say, though FireTexts founder Alex Vilenchik has noticed a divide.

"I don't know a single female user besides my girlfriend," he said.

The dating apps make their move

As these helpers grow, the big dating apps are threatening to make them obsolete

Dating apps are increasingly incorporating AI advisors. Tinder has an AI photo selector; Hinge offers advice on opening lines. Grindr is piloting its own Wingman product, and Chief Product Officer AJ Balance said that feedback has been positive.

The space is ripe for an acquisition, though none of the founders seems to be biting. Rizz's Khaves said that Match Group's CTO approached him in 2023, but talks ended when Khaves wasn't interested in an acquihire.

YourMove's Mirakyan said that he's had talks with multiple major dating app companies. Roast's Baylin said he talked to Bumble and Match Group — and is unimpressed with the latter's current efforts. Match Group declined to confirm any past potential acquisition conversations; Bumble did not respond to a request for comment.

"When we see the Tinder photo selection, it's really far behind in terms of tech," Baylin said. "If you take 20 selfies of yourself, those 20 are going to pop up as the potential photo options."

(I tested the photo selector for myself — while it didn't pick only selfies, it did pick entirely solo shots, breaking the classic dating app rule that you want at least some group shots to prove you have friends.)

Other founders seemed skeptical about the major dating apps' entrance into the space. Wingman founder Rob Mariani and FireText's Vilenchik both suggested that the companies were too politically correct to be helpful.

"Are they able to make their AI say, 'Well, dude, have you considered losing weight?'" Mariani said. "That's a very impolite thing to say. I don't know if they have it in them to do that."

Then there are the AI pioneers themselves. The makers of foundation models and the chatbots they power pose another threat to the AI wingman startups. ChatGPT can generate suggestions for dating app messages or provide feedback for profiles. OpenAI will soon allow erotica for adults, per its CEO Sam Altman, opening up even more opportunities.

The startup founders must convince daters to seek out a specialized product — and even pay a subscription fee — rather than turning to a traditional chatbot or a built-in AI tool on their go-to dating app.

Am I being chatfished?

Then the thornier question remains: Do singles want to bring AI into their dating lives in the first place?

The Kinsey Institute at Indiana University conducts an annual survey of 5,000 daters in partnership with Match Group. This year, 26% of respondents said that they were using AI while dating. That figure jumped to 38% for active daters.

Kinsey Institute research scientist Amanda Gesselman said she heard anecdotally that some daters felt like they were chatting with bots. 33% of respondents said that using AI to generate an entire conversation was a dealbreaker. The daters were more receptive to an AI-generated opening line, she said.

The biggest sore spot was AI-altered photos, with 40% calling it a dealbreaker.

There's still some hesitancy from the dating apps, too. While Tinder invests in its AI photo selector, it's still holding back from fully artificial conversations. Claire Watanabe, Tinder's senior director of product, wrote in an email to Business Insider that Tinder should "never feel like a sea of chatbot-generated content."

"Internally, we've even joked about removing the paste function or adding an em dash detector to flag suspiciously 'AI-ish' writing," Watanabe wrote. "It's half-serious, but the intent is real."

Despite all the efforts, it's still unclear whether AI wingmen are a fad or the future. Daksha Franklin, a 36-year-old clinical hypnotherapist from Los Angeles, asked ChatGPT to spruce up her dating profile — and wasn't thrilled with the results.

"I just didn't like it, so I went with my own words," she said.

Franklin isn't an AI pessimist, though. She also asked ChatGPT to describe her dream man so she could narrow down her preferences.

The chatbot nailed it.