Artificial intelligence is revolutionizing modern dating, with millions of singles now turning to AI chatbots like ChatGPT and specialized dating assistant apps for everything from crafting pickup lines to deciding when to send that crucial first text. This emerging trend represents a significant shift in how people approach romantic relationships in the digital age.
Rebecca Koltun, a 26-year-old from Florida, exemplifies this new generation of AI-assisted daters. When she met a man in a VIP club section, she consulted ChatGPT about whether to text first. The AI advised her to wait, predicting he was accustomed to female attention. A week later, he texted her—validating the chatbot’s strategy.
The AI dating assistant market is experiencing explosive growth, led by bootstrapped startups that are now profitable and attracting attention from major dating platforms. Rizz, founded by Roman Khaves in 2022, has accumulated 13 million downloads and maintains 400,000 monthly active users. The app analyzes dating app screenshots to provide witty replies and compatibility scores. Competitors like YourMove (over 1 million downloads) and Roast (nearly 100,000 paying users) are rapidly expanding their user bases.
Major dating platforms are taking notice. Match Group and Bumble have reportedly engaged in acquisition talks with these startups, though founders like Khaves have declined offers. Meanwhile, established dating apps are developing their own AI features: Tinder offers an AI photo selector, Hinge provides opening line advice, and Grindr is piloting its own Wingman product.
User demographics reveal interesting patterns. Chase Dennis, an 18-year-old student, uses ChatGPT to generate jokes and rhymes for DMs, editing the output to maintain authenticity. FireTexts founder Alex Vilenchik noted a gender divide, saying he doesn’t “know a single female user besides my girlfriend.”
However, concerns about authenticity are mounting. The Kinsey Institute’s annual survey of 5,000 daters found that while 26% use AI in dating (rising to 38% for active daters), 33% consider AI-generated entire conversations a dealbreaker. The phenomenon has spawned new terminology like “chatfishing”—using AI-altered voices or messages to deceive potential partners.
The competitive landscape includes three major players: specialized startups, traditional dating apps, and foundation model makers like OpenAI. With Sam Altman announcing that ChatGPT will soon allow adult erotica, the boundaries of AI-assisted romance continue to expand.
Key Quotes
Chat told me no. 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.
Rebecca Koltun, a 26-year-old ballet nonprofit worker, explaining ChatGPT’s dating advice that successfully predicted a man would text her first. This quote illustrates how users are trusting AI for strategic romantic decisions.
I’ve been nervous to tell them because they might think I’m unoriginal, but honestly, I think I’m pretty iconic.
Chase Dennis, an 18-year-old student who uses ChatGPT for pickup lines, discussing his transparency with potential dates. This reveals the tension between using AI assistance and maintaining authenticity in dating.
Internally, we’ve even joked about removing the paste function or adding an em dash detector to flag suspiciously ‘AI-ish’ writing. It’s half-serious, but the intent is real.
Claire Watanabe, Tinder’s senior director of product, expressing the platform’s concerns about AI-generated content. This demonstrates how dating apps are grappling with maintaining authentic human connection while incorporating AI features.
When we see the Tinder photo selection, it’s really far behind in terms of tech. If you take 20 selfies of yourself, those 20 are going to pop up as the potential photo options.
Benoit Baylin, cofounder of Roast, critiquing established dating apps’ AI capabilities. This highlights the competitive advantage specialized AI dating startups believe they hold over traditional platforms.
Our Take
The AI dating assistant phenomenon represents a fascinating collision between technological capability and human vulnerability. What’s particularly striking is the speed at which this market has matured—from viral novelty to profitable businesses courted by industry giants in just two years. The gender divide in usage patterns suggests men may feel more pressure to optimize their approach, while the 33% dealbreaker statistic reveals a cultural red line around full automation of romantic conversation. The real disruption may not be the technology itself, but how it’s reshaping expectations: if AI-optimized profiles and messages become the norm, those who don’t use these tools may find themselves at a competitive disadvantage. This creates a potential arms race dynamic where AI assistance becomes necessary just to maintain parity. The irony is profound—technology designed to help people connect may ultimately make authentic human connection more elusive, as daters increasingly wonder whether they’re interacting with a person or an algorithm.
Why This Matters
This story signals a fundamental transformation in human courtship and social interaction, representing one of AI’s most intimate applications yet. The rapid adoption of AI dating assistants—with 38% of active daters already using the technology—demonstrates how quickly artificial intelligence is penetrating personal aspects of life previously considered uniquely human.
The business implications are substantial. The emergence of profitable, bootstrapped startups in this space, combined with major dating platforms’ scramble to develop competitive features, suggests a significant market opportunity. Match Group and Bumble’s reported acquisition interest indicates that established players view AI assistance as essential to their future competitiveness.
Societally, this raises critical questions about authenticity and human connection. When 33% of daters consider AI-generated conversations dealbreakers, yet millions continue using these tools, we’re witnessing a cultural negotiation about acceptable AI boundaries in romance. The emergence of terms like “chatfishing” suggests growing awareness of potential deception. This trend may fundamentally alter how future generations form relationships, potentially creating a divide between AI-assisted and “organic” dating approaches, with lasting implications for social norms and expectations around courtship.
Related Stories
- PwC Hosts ‘Prompting Parties’ to Train Employees on AI Usage
- Google’s ‘Ask for Me’ AI Phone Tool: A Game-Changer for Time Management
- Teen Suicide Lawsuit Targets Character.AI Chatbot and Google
Source: https://www.businessinsider.com/ai-wingman-dating-helper-tinder-hinge-pickup-lines-chatgpt-2025-12