I Asked ChatGPT to Help Me With My Dating Anxiety. Here's...

What’s Happening

Here’s the thing: Plus, what an actual sex therapist had to say about the AI’s answers.

Below is the real, full chat transcript of an exchange between a Men’s Health reader seeking sex and dating advice — we’ll call him “William” — and ChatGPT. We showed this back-and-forth to Rufus Spann, PhD , sex therapist and founder of Libido Health, and asked him for his thoughts on the quality and applicability of the advice. (it feels like chaos)

WILLIAM: Hey Chat, I’ve been struggling the last three years with women, could you help me figure out some ways to improve my chances of finding a girlfriend?

The Details

What are some questions to get us kicked off? Please keep responses to 100 words or less.

ChatGPT: Totally—happy to help. Let’s start by getting a clear picture.

Why This Matters

Answer whatever feels easy: What’s been hardest lately: meeting women, getting dates, or keeping momentum? Where do you usually meet women (apps, friends, work, hobbies)? How do you feel on dates—confident, nervous, unsure what to say?

Health experts are weighing in on what this means for people.

Key Takeaways

• What kind of relationship are you actually looking for?
• What feedback (if any) have you gotten after dates?
• How’s your social life overall?
• What do you like about yourself as a partner?

The Bottom Line

I try to come across as confident but I think I probably comes across as shy, I find myself thinking too hard about what to say next, or there would be awkward lulls in our conversation. I would love to find a long term GF to start the next part of my life, I’m already 33!

Is this a W or an L? You decide.