“I don’t know — ask Chat.”
It’s something I say all the time. When I’m double-checking if a work email sounds professional, fact-checking whether the Nile is actually the longest river in the world, or settling a random debate over dinner, the answer is always, ask Chat.
Lately, though, that sentence has found its way into my group chats for a very different reason. Not for work. Not for trivia. But for love…or at least, whatever version of it exists on dating apps in 2025.
I’ve found myself and my friends more and more often turn to ChatGPT to help decode the behavior of men: what a casual invitation to dinner really means, how long we should wait before replying, or whether silence equals ghosting.
What a world we live in where we now turn to a computer to understand human behavior. How somewhere between professionalism and emotional survival, we have landed on AI as the new relationship therapist.
Minutes before deciding to ponder this through a new blog post I was drafting up a dating question of my own.
Running the risk of exposing myself to an almost certain humiliation (the things I do for you guys) I thought I’d share some of my own musings to Chat.
Chat excerpt:
Me: A man I’ve gone out on a few dates with texted me “Would like to have a night in with you.” He’s kind of alluded to coming over twice now, but I’m not sure what his expectations are for the night. I don’t want to have like a heavy intention talk but how do I send a message that gauges this?
Chat Bot: Got it — you want to lightly gauge his intention without making it into a big, heavy “what are we” convo. You can do that with a playful or curious tone that leaves him room to clarify. A few options you could send back:
- Playful curiosity:“Mmm a night in… what exactly do you have in mind 👀”
- Light but clear:“When you say a night in, are we talking movies and takeout or something else? 😏”
- Teasing:“You’ve mentioned this night in a couple times now what are you plotting?”
Each one keeps it fun while nudging him to be clearer about whether he’s just thinking casual hangout or hinting at something more.
Do you want me to make the tone more flirty or more casual-safe (so you don’t risk misreading him)?
Me: Okay I said the second prompt and he’s saying “like hanging out at mine or yours that he’s cooking and would like my company.” I want to say something like I’d be open to doing that sometime but think we should get to know each other a bit more first like that I’m not trying to move fast and we’ve only been on two dates. Do I sound crazy?
Chat Bot: You definitely don’t sound crazy — that’s a very normal and healthy boundary, especially after just two dates. The key is to keep it light and warm so it doesn’t feel like a rejection, just you setting the pace. Here are a few ways you could phrase it:
- Warm + clear:“That sounds really sweet, I’d definitely be open to that sometime. I just feel like since we’ve only had a couple dates, I’d love to get to know you a little more first 😊.”
- Playful but sets boundary:“A home-cooked meal does sound tempting but since we’ve only been out twice, maybe let’s have a couple more adventures first 😉.”
- Direct but kind:“I’d be open to that eventually. I just want to take things slow and get to know each other a bit more first.”
This way you’re not shutting him down — you’re showing interest, just setting the pace that feels good to you.
So…is AI even a valid tool for dating advice?
Given that 13.3 million people lean on ChatGPT weekly for some form of relationship or personal reflection, it’s worth asking the question.
And honestly? In moments like the one above, yes, AI can be a surprisingly solid co-pilot.
For me, it’s been a helpful way to communicate clearly without spiraling, set boundaries without sounding intense, and send messages that don’t read like I rewrote them 17 times.
It’s also always there (the unfortunate upside), and most of the feedback is neutral and non-judgmental. No projecting. No “ugh girl dump him.” No trauma-bonded hot takes. And we all have that one friend — the man-hater who’s been wronged enough times to turn every situation into a cautionary tale.
My advice: do not, under any circumstance, take dating advice from someone who is actively scorched-earth about men. They will talk you out of anything good.
But — and this is where AI shows its cracks — it can only help you with the information you give it. Leave out one detail, soften something, exaggerate something, or interpret a tone wrong, and the advice shifts. It also can’t read energy:
the tension in a room,
the way someone looks at you,
the softness or sharpness in their voice,
the chemistry.
It only knows the typed version of a moment, which is always the sanitized, abridged, written in your point of view version and that’s never the full story.
So AI works best as a tool, not a compass.
Great for the draft.
Not great for the decision.

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