AI Wingmen: The New Trend in Online Dating

Artificial intelligence is rapidly transforming the dating landscape, serving as a digital wingman for millions of users. Singles are increasingly using tools like ChatGPT to generate witty pick-up lines, craft dating app bios, and receive real-time advice on whether to text a match. This shift has given rise to a thriving startup ecosystem, with apps like Rizz and YourMove offering specialized assistance and reporting millions of downloads.

Simultaneously, major dating platforms such as Tinder and Hinge are incorporating AI features into their own services, from photo selection to opening line suggestions. However, the integration of AI into romance raises new questions about authenticity and connection. While some users praise the efficiency of AI coaching, others worry about the prevalence of 'chatfishing' and the potential for inauthentic interactions. As the technology evolves, the debate continues over whether AI is a helpful tool or a barrier to finding love.

For many singles, ChatGPT has become a go-to resource for navigating the complexities of modern romance. Rebecca Koltun, a 26-year-old from St. Petersburg, Florida, consulted the AI when she met a man at a club in Tampa. Instead of asking friends, she asked the chatbot if she should text him first.

The AI advised patience, telling Koltun that a man in the VIP section is used to attention and that the best move was to wait. "Chat told me no," Koltun said. "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 reached out, confirming the AI's strategy worked.

Others, like 18-year-old student Chase Dennis, use the technology to break the ice. Dennis asks ChatGPT for jokes or rhymes to slide into DMs, though he edits the output to maintain his own voice. While he admits some recipients think he is a "cornball," he often reveals the AI origin, which he says is usually received with humor.

The use of AI extends beyond simple conversations. Daters utilize chatbots to refine their profiles and seek therapy-like advice for anxious moments. This widespread adoption is reshaping expectations and creating a new vocabulary for digital romance, including the term "chatfishing."

The demand for AI dating assistance has created a booming market for specialized startups. Leading the pack is Rizz, founded by Roman Khaves in 2022. The app, which offers witty replies and compatibility scores based on chat screenshots, has been downloaded 13 million times and maintains 400,000 monthly active users. Khaves notes that the app was profitable from the start and that he has turned down venture capital offers.

Following Rizz are several competitors gaining traction:

• YourMove: Founded in 2022, it has surpassed 1 million downloads.
• Roast: Founded in 2024, it claims millions of free users and nearly 100,000 paying subscribers.
• Wingman: Has secured 4,700 paying customers.
• FireTexts: Sees 10,000 installs per month.

Despite the growth, there appears to be a gender divide in usage. Alex Vilenchik, founder of FireTexts, noted, "I don't know a single female user besides my girlfriend."

These startups face competition not just from each other, but from the foundational AI models themselves. With OpenAI planning to allow more adult content, the capabilities of general chatbots are expanding, challenging specialized apps to prove their unique value.

Established dating giants are responding to the AI trend by integrating similar features directly into their platforms. Tinder has introduced an AI photo selector, while Hinge offers AI-generated advice on drafting opening lines. Grindr is currently piloting a Wingman product, with Chief Product Officer AJ Balance reporting positive feedback.

This move by industry heavyweights threatens to make standalone AI startups obsolete. However, startup founders remain critical of the incumbents' efforts. Benoit Baylin of Roast described Tinder's photo selection technology as "really far behind," noting that it simply surfaces all selfies rather than curating a balanced profile.

Acquisition talks have reportedly taken place between the startups and major players. Roman Khaves was approached by Match Group's CTO in 2023, though talks ended due to a lack of interest in an acquihire. Similarly, Dmitri Mirakyan of YourMove and Baylin of Roast have held discussions with Match Group and Bumble. Match Group declined to confirm acquisition talks, while Bumble did not respond to requests for comment.

Some startup founders, such as Rob Mariani of Wingman, believe the major apps are too "politically correct" to offer the blunt advice that daters might actually need.

Despite the technological advancements, significant questions remain regarding the ethics and effectiveness of AI in dating. A survey conducted by the Kinsey Institute in partnership with Match Group found that 26% of respondents use AI while dating, a figure that jumps to 38% among active daters. However, 33% of respondents stated that using AI to generate an entire conversation was a dealbreaker.

The most significant sore spot for daters is AI-altered photos, with 40% calling it a dealbreaker. This concern is shared by dating apps themselves. Claire Watanabe, Tinder's senior director of product, emphasized that the platform should "never feel like a sea of chatbot-generated content," even joking about adding detectors for suspiciously 'AI-ish' writing.

Individual experiences vary. Daksha Franklin, a 36-year-old clinical hypnotherapist, asked ChatGPT to spruce up her dating profile but ultimately rejected the results, preferring her own words. However, she found the AI helpful in describing her dream man, which helped narrow her preferences.

As the technology matures, the industry faces a pivotal moment. Whether AI remains a helpful wingman or becomes a hindrance to authentic connection depends on how daters and platforms balance efficiency with the human element of romance.