We Asked AI To Be Our Ultimate Dating Wingman—Here’s What Happened

AI isn’t just answering emails anymore—it’s running your love life. From opening lines to breakup texts, we asked ChatGPT to be the ultimate dating wingman. Here’s how it went (plus actual prompts you can steal).

Once upon a time, your best friend was the go-to for decoding a cryptic “wyd?” text. Now? AI is stepping in. From flirty DMs to full-blown relationship strategies, people are outsourcing their love lives to chatbots. So we had to ask—could AI really be the ultimate dating wingman?

We put it to the test, asking ChatGPT to handle every stage of modern romance, from the first text to the last goodbye. The results? Equal parts impressive, chaotic, and slightly terrifying.

1. The Flirty Opener

Crafting the perfect first message is an art. You want charm, intrigue, and a little wit—without sounding like you tried too hard (even though you did). So we asked AI:

“Give me a Hinge opening line that’s funny, flirty, and makes them want to respond.”

ChatGPT: “Two truths and a lie: 1. I make a mean margarita. 2. I’ve been skydiving. 3. I didn’t overthink this message at all.”

Verdict? Not bad. A little “I’m so chill” coded, but better than the usual “Hey :)”.

2. The ‘I Need A Date Idea That’s Not Just Drinks’ Situation

Let’s be honest—“Let’s grab a drink?” is the lazy man’s approach to dating. So we threw this at AI:

“Plan a date that’s unique, low-pressure, and makes me seem effortlessly cool.”

ChatGPT: “Take them to an art exhibit but make it a game—whoever finds the weirdest piece wins a round of cocktails.”

Okay, ChatGPT, we see you. Effortless? No. Cool? Absolutely.

3. The Late-Night Reply That’s Not A Cringe Fest

There’s a science to responding to a risky “You up?” text. Say too little, and you seem disinterested. Say too much, and you’re that person. AI’s take?

“Give me a reply to a ‘You up?’ text that’s playful, flirty, and makes them regret sending it.”

ChatGPT: “Only if you’ve got a compelling reason for me to be.”

A little mysterious, a little cocky—honestly, not bad.

4. The ‘I Need to End This, But Nicely’ Text

Not every situation calls for ghosting (tragic, we know). So we gave AI the toughest task of all:

“Write me a short but kind text to let someone down gently.”

ChatGPT: “I’ve really enjoyed getting to know you, but I don’t think this is quite the right fit. You’re great, and I wish you all the best.”

Straightforward, mature, emotionally stable—everything we don’t want to be when breaking up with someone.

5. The Spicy Role-Playing Request (Yes, We Went There)

And then, we entered uncharted territory. Turns out, people are using AI to practice, ahem, steamy conversations before they bring them into real life. So we asked:

“Write me a text that subtly hints at something spicy, but in a way that feels classy and intriguing.”

ChatGPT: “Let’s just say… if I told you what I was thinking right now, you’d be very distracted for the rest of the day.”

Okay, AI gets it.

The Verdict? AI Might Actually Be Your Best Wingman

Does AI feel things? No. Will it help you avoid sending a “wyd” text at 2 AM? Yes. And honestly? That’s already a win.

Just one final tip? Before you hit send, remove the double quotes. No one needs to know AI wrote your text—except you.