I Asked ChatGPT to Help Me With My Dating Anxiety. Here's What It Told Me.
Men's Health
February 14, 2026
AI-Generated Deep Dive Summary
A man named William turned to ChatGPT for help with his dating anxiety, seeking advice on improving his chances of finding a long-term girlfriend after struggling for years. The AI provided a series of thoughtful questions aimed at identifying specific issues, such as difficulty converting conversations into dates and concerns about appearing confident versus shy. William revealed challenges like feeling unsure during interactions, stalling conversations, and worrying about his appearance and ability to engage thoughtfully with potential partners.
ChatGPT’s structured approach focused on addressing practical concerns, offering advice tailored to building confidence and momentum in social situations. For instance, the AI suggested focusing on clean, intentional fashion choices rather than trendy styles and recommended asking for dates sooner—within two to three days of meeting someone—to maintain the positive vibe. The AI also emphasized that William’s value lies not in external appearances but in his reliability and ability to connect with others on a deeper level.
While ChatGPT provided actionable tips, sex therapist Rufus Spann, PhD, highlighted the importance of combining AI-driven insights with professional guidance for a well-rounded approach. Spann noted that adopters of AI tools like ChatGPT should view them as collaborators rather than replacements for human expertise. By leveraging both technology and expert advice, individuals can gain a more comprehensive understanding of their challenges and develop strategies to improve their social and dating lives.
This story underscores the growing role of AI in addressing personal growth and emotional well-being, offering readers a modern approach to overcoming dating anxiety. For those struggling with similar issues, integrating AI tools with professional advice can provide a powerful framework for building confidence and improving relationships. Ultimately, this highlights the importance of self-awareness and willingness to seek support—whether through technology or human interaction—in fostering healthier, more fulfilling connections.
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Originally published on Men's Health on 2/14/2026