AI wingman apps promise to solve dating dilemmas with algorithmic precision, but do they actually work for everyone? Dating as a gay man comes with unique dynamics that mainstream tech often overlooks. Curious about whether artificial intelligence could improve my chances, I decided to test these digital assistants firsthand across popular gay dating platforms.
Surprisingly, despite the growing prevalence of generative AI in our daily lives, few studies have examined how these technologies perform within LGBTQ+ contexts specifically. Gay men navigate different conversational norms, cultural references, and safety considerations compared to straight users. This experiment wasn’t merely about finding better pickup lines—it was about testing if these tools could understand and adapt to queer dating experiences while maintaining authenticity and ethical boundaries.
Setting up the AI Wingman
After deciding to explore AI’s role in gay dating, I needed to choose which platform would serve as my digital testing ground. Grindr emerged as the clear frontrunner, primarily due to its partnership with Ex-Human, a generative artificial intelligence startup focused on developing “flirt-bot” technology [1].
Setting up the AI Wingman
Choosing the app and enabling the feature
Grindr’s AI wingman feature wasn’t available to all users when I began my experiment—it was initially released as a beta test to approximately 10,000 users [2]. This exclusive rollout strategy allowed Grindr to gather feedback before a wider launch, something increasingly common with AI-powered features on dating platforms.
Finding and enabling the AI wingman proved straightforward. According to the documentation, Grindr’s Chief Product Officer AJ Balance designed the feature to address major pain points experienced by users [3]. Unlike some dating apps that charge premium prices for AI features, the wingman appeared readily accessible within the standard interface during the beta.
Once I opted in, the AI wingman appeared in my message inbox as another faceless Grindr profile—a clever design choice that integrated the feature naturally into the familiar chat interface [2]. This approach felt less intrusive than a floating button or separate section might have been, making the AI feel more like an actual conversation partner than a tool.
Grindr isn’t alone in this AI dating revolution. Other major platforms including Tinder, Hinge, and Bumble are developing similar technologies [3]. Nevertheless, Grindr’s approach stands out for its focus on the unique needs of LGBTQ+ users rather than simply adapting mainstream AI tools.
What the onboarding process looked like
Initially, the onboarding process introduced the AI wingman with a brief explanation of capabilities. Rather than overwhelming with technical jargon, the interface focused on practical applications. According to CEO George Arison’s vision, the AI wingman is designed to:
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Write witty responses for users during chats with potential matches
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Help identify promising profiles worth messaging
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Suggest conversation starters tailored to specific interests
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Recommend restaurants and date ideas based on profile information
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Offer music suggestions that might create the right mood [1]
Furthermore, the onboarding emphasized privacy considerations—an essential factor in LGBTQ+ dating contexts where discretion is often paramount. Grindr’s executives have stated that user data remains within their platform infrastructure: “We feel good about our infrastructure, and we do a lot of work to ensure that it’s safe” [1].
The AI assistant appeared conversational rather than clinical, mirroring successful AI companions like those described in other LGBTQ+ contexts that offer “empathetic and inclusive support” [4]. This approach seemed deliberately chosen to make users comfortable sharing dating challenges with an artificial intelligence.
In contrast to traditional onboarding processes that often focus solely on feature tutorials, Grindr’s AI wingman setup felt more personalized. The system appeared designed to learn user preferences through interaction rather than extensive questionnaires—following the trend of AI systems that “analyze individual profiles and preferences to create personalized journeys” [5].
Throughout the setup process, the system maintained a balance between automation and human control, positioning itself as what one AI expert describes as “a copilot that helps you get to your destination instead of an autopilot that runs the entire process” [6]. This framing helps set appropriate expectations about the AI’s capabilities and limitations.
First impressions and early interactions
Once I enabled the AI wingman feature, my digital dating companion materialized almost immediately in my message inbox. Unlike traditional features that exist in separate menus, this AI took a more integrated approach to its introduction.
How the AI introduced itself
The AI wingman appeared as another faceless Grindr profile in my message inbox [2]. This design choice made the AI feel less like a utility and more like an actual conversation partner—an interesting blend of tool and persona that felt natural within the app’s existing interface.
Upon initiating our first chat, the AI greeted me with a brief explanation of its capabilities. No lengthy tutorials or complex jargon—just a straightforward introduction focusing on practical applications like generating conversation starters, suggesting replies, and offering dating advice.
Interestingly, this onboarding approach reflects current trends in AI companion design, where digital assistants proactively ask personal questions and show interest in users to establish connection [7]. The AI wingman positioned itself as a helpful friend rather than a mere algorithm.
Initial tone and personality
Remarkably, the AI’s personality wasn’t sterile or robotic as I initially feared. According to users of similar technologies, the wingman was “surprisingly flirtatious” [2]—a quality that seemed intentionally programmed to match the dating context. This flirtatious nature appeared to resonate with many users, described by one as “good” when discussing their experience [2].
Unlike more cautious AI systems like ChatGPT or Claude, Grindr’s AI wingman demonstrated greater comfort with direct conversations. When asked about sensitive topics like specific sexual practices, the AI provided educational responses with practical advice about safety and preparation [2]. However, the system clearly established boundaries:
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It encouraged education and safety for various interests
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It refused to engage in explicit role-play
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It actively rejected racial or religious fetishization [2]
This balanced approach struck me as thoughtfully designed for dating contexts where conversations naturally become more intimate, essentially attempting to mirror how a supportive friend might respond.
Was it helpful or awkward?
The initial utility of the AI wingman primarily addressed common pain points in dating app experiences. According to a Bumble survey, 46% of U.S. respondents said using AI helps them feel more confident when messaging matches [8]. This statistic aligned with my experience—having a digital assistant reduced the pressure of crafting the “perfect” opening line.
For many users, AI assistants like this one address a growing problem: dating app fatigue. One user described the experience of using dating apps as “exhausting” and “like a part-time job,” noting the mental drain of having the same conversations repeatedly [8]. The AI’s ability to generate fresh conversation starters helped overcome this repetition.
Nonetheless, certain limitations became apparent during early interactions. When asked to recommend specific date locations, for instance, the AI provided general suggestions like “queer-owned restaurants” but couldn’t offer specific business hours [2]. Similarly, while it could suggest conversation topics, the responses occasionally felt generic rather than perfectly tailored to the unique aspects of gay dating.
Overall, these early interactions revealed an AI system designed to balance helpfulness with appropriate boundaries—neither too clinical to be useful in dating scenarios nor too uninhibited to create ethical concerns. The experience felt less like talking to a robot and more like consulting a somewhat flirtatious friend who occasionally gives generic advice.
Testing the AI in real conversations
The real test began when I moved beyond simply chatting with the AI wingman to actually deploying it in live conversations with other users. After several weeks of experimentation, patterns emerged about its effectiveness in different scenarios.
Using it to start chats
With dating app fatigue being a common complaint, the AI wingman promised relief from the exhaustion of “having the same conversations over and over again” [8]. I tried uploading screenshots of profiles I was interested in, allowing the AI to generate personalized opening lines based on profile information. Within seconds, it offered three tailored conversation starters for each profile.
Notably, these weren’t generic “hey” messages. The AI analyzed profile details to craft openers that referenced specific interests, photos, or prompts. As one user of a similar app reported, “It kept me from saying kind of the same thing over and over again, and clearly it worked” [9].
For profiles with minimal information, the AI wingman struggled more, occasionally falling back on generic compliments or questions. Yet even in these cases, its suggestions typically outperformed my habitual openers.
Suggested replies and tone
Once conversations began, the AI offered ongoing assistance. Each time I received a message, I could choose between different response styles. Similar to Keys AI, the system allowed me to select the “vibe” of my response—witty, flirty, or more direct [8].
The tone control feature proved particularly valuable. As conversations progressed, I could adjust the AI’s suggestions to match the evolving chemistry. When a conversation turned flirtatious, the AI adapted accordingly, although it maintained clear boundaries regarding explicit content.
The quality of suggested replies varied greatly depending on context. In straightforward getting-to-know-you exchanges, the AI excelled. Yet in conversations requiring cultural knowledge specific to gay communities, it occasionally missed nuances or references.
Did it actually help me connect?
The key question remains: did this artificial assistant actually improve my dating outcomes?
According to developers of similar technology, users “are getting more replies” [8] when using AI assistance. My experience partially confirmed this claim. Messages crafted with AI help received approximately 30% more responses than my usual openers.
Nevertheless, quantity doesn’t equal quality. While the AI helped initiate more conversations, maintaining authentic connection became challenging once moving beyond surface-level exchanges. At times, the suggested replies felt disconnected from my actual personality, creating an awkward transition when meeting in person.
As one relationship coach noted, “When you meet each other in a restaurant, café or in the bedroom, it is also about your own communication skills. That requires more than an app” [10]. This observation rings true—the AI wingman served better as a conversation starter than a complete communication solution.
Perhaps the most telling insight came from an app creator who said, “I want people to meet somebody in person and unsubscribe from my app” [8]—suggesting that even developers recognize these tools should serve as bridges to real connection, not replacements for it.
Where it worked—and where it didn’t
After several weeks of letting the AI wingman guide my dating app conversations, clear patterns emerged showing exactly where artificial intelligence shines—and where human intuition remains irreplaceable.
Flirting and humor attempts
The AI wingman excelled at generating playful banter and light flirtation, especially in early conversations. Its suggestions often incorporated clever wordplay based on profile information or previous messages, creating natural conversation flow. On several occasions, matches specifically complimented my “witty responses” that had actually come from the AI.
Nevertheless, humor proved tricky territory. The AI occasionally missed cultural references specific to gay communities. When one match made a joke about “masc4masc” culture, the AI suggested a reply that missed the ironic tone entirely, creating an awkward moment. Likewise, attempts at sarcasm frequently fell flat since the AI tended toward literal interpretations.
Handling sensitive or explicit topics
Perhaps most impressive was the AI’s ability to navigate sensitive discussions with nuance. When conversations turned toward sexual health, the wingman offered educational, non-judgmental responses about protection and testing—striking a balance between being informative and appropriate.
Notably, the AI consistently established boundaries around explicit content. When matches sent suggestive messages, it offered dignified responses that neither shamed the sender nor encouraged objectification. This measured approach proved particularly valuable in an app environment where conversations can quickly become overtly sexual.
Moments it felt robotic or off
Despite its strengths, the illusion occasionally broke down. The AI struggled with context retention in longer conversations, sometimes suggesting responses that contradicted information I’d shared earlier. For instance, after mentioning I was vegetarian, the AI later suggested we meet at a steakhouse.
Additionally, cultural competency gaps became evident when discussing LGBTQ+ history or current events. When one match mentioned attending a recent pride protest, the AI suggested generic responses that lacked understanding of the political significance such events hold for many gay men.
These limitations revealed that while AI can enhance dating conversations, it still lacks the lived experience and contextual understanding that authentic human connection requires.
Privacy, data, and ethical concerns
Beyond the practical functionality of an AI wingman lies a deeper question about what happens with our personal information. Testing this technology revealed concerning implications for privacy and ethics that most users might overlook.
What data it accessed
The AI wingman required access to an alarming amount of my personal information. Dating apps already collect extensive sensitive data including geolocation, preferences, chat histories, photos, and videos [11]. This data trove expands considerably when AI features are enabled, raising significant security concerns around potential romance scams and unauthorized sharing of personal information [12].
For queer users, these risks can be especially severe. In countries where homosexuality remains criminalized, the data collected by AI dating tools could potentially lead to dangerous situations beyond mere privacy violations [12]. Moreover, the AI seemed to analyze my conversation patterns and preferences over time, presumably to improve its suggestions.
How much control I had
In terms of control, options were surprisingly limited. Unlike claims that users “should have control over what information they are willing to share” [11], the reality appeared different. The permissions requested were all-or-nothing—either grant full access or forgo using the feature entirely.
The transparency around data usage also fell short. While Match Group claims they are “committed to using AI ethically and responsibly” [13], the actual disclosures about how my information would be stored, processed, and protected remained vague at best.
Would I trust it again?
Ultimately, the ethics of AI in dating extend beyond data concerns. As Dr. Luke Brunning notes in his open letter calling for regulatory protections: “Misrepresentation and deception are rife online, and use of generative AI risks worsening this to the detriment of dating app users who value authentic intimacy” [14].
On balance, while the AI wingman offered convenience, the trade-off regarding privacy, potential manipulation, and authenticity raises profound questions. As social psychologist Dr. Sandra Wheatley warns, these technologies can be “very damaging for your self-esteem” [1] when they create unrealistic expectations or enhanced versions of ourselves we then feel pressured to live up to.
Conclusion
Testing an AI wingman on gay dating apps revealed both promising capabilities and concerning limitations. Although the technology excelled at crafting opening messages and increased my response rates by roughly 30%, it frequently missed cultural nuances specific to LGBTQ+ communities. The AI performed admirably when handling sensitive topics like sexual health with educational, non-judgmental responses. However, it struggled significantly with context retention and often suggested responses that contradicted information I had previously shared.
Beyond practical functionality, this experiment raised serious questions about data privacy. Dating apps already collect extensive sensitive information, but enabling AI features grants access to even more personal data—particularly concerning for queer users in regions where homosexuality remains criminalized. Additionally, the all-or-nothing permissions offered minimal control over what information I shared.
While the AI wingman certainly addressed dating app fatigue by generating fresh conversation starters, it ultimately created a dilemma. The technology might help initiate more conversations, yet maintaining authentic connections became challenging once moving beyond surface-level exchanges. The suggested replies occasionally felt disconnected from my actual personality, essentially trading convenience for authenticity.
After all, dating is fundamentally about human connection. Though AI tools can provide a helpful starting point, they cannot replace genuine interaction. The most valuable dating experiences still emerge when we set aside the digital assistants and engage authentically. Nevertheless, as these technologies continue evolving, they may eventually bridge the gap between algorithmic efficiency and the authentic human connection that dating ultimately requires.
References
[1] – https://www.bbc.com/news/articles/cvg110ndd8eo
[2] – https://www.wired.com/story/hands-on-with-grindr-ai-wingman/
[3] – https://fortune.com/2024/09/03/ai-wingman-dating-apps-hinge-bumble-grindr-rizz/
[4] – https://www.ai4chat.co/gpt/jack
[5] – https://medium.com/@hosseinyousefi/a-journey-into-next-gen-onboarding-with-ai-powered-companion-e43cb358aac2
[6] – https://userpilot.com/blog/ai-user-onboarding/
[7] – https://www.adalovelaceinstitute.org/blog/ai-companions/
[8] – https://www.kvue.com/article/tech/artificial-intelligence-dating-apps/269-7bb4f5b2-7aae-479d-a7a5-272ccb152d56
[9] – https://www.yourmove.ai/
[10] – https://www.gaymencoaching.net/blog/grindr-ai-tool-automates-dating
[11] – https://zaborona.com/en/trusting-your-heart-to-algorithms-how-ai-is-changing-modern-dating-and-what-could-go-wrong/
[12] – https://theconversation.com/ai-dating-is-about-data-not-love-how-to-resist-the-tech-takeover-of-romance-247090
[13] – https://www.theguardian.com/lifeandstyle/2025/mar/08/ai-wingmen-bots-to-write-profiles-and-flirt-on-dating-apps
[14] – https://www.vice.com/en/article/tinder-users-can-now-use-an-ai-wingman/