First dates: sometimes they feel like magic. Other times, they feel like two strangers playing polite ping-pong with facts about their jobs, favorite cuisines, and that one time they “found themselves” in Tulum.

But, what if you could skip the boring small talk and the trauma overshare… and still get to the good stuff? No job interview energy. No free therapy session. Just good, honest convo that’s flirty and fun?

Here are 5 first-date conversation starters that are equal parts charming, real, and second-date-worthy…

1. The Thing That’s Currently Taking Over Your Brain (And Isn’t Work)

I’m begging you—please don’t just talk about your job. Unless you're a dolphin trainer or a pastry chef at a secret Michelin-star speakeasy, keep it brief.

Instead, talk about what’s actually lighting you up right now. A podcast you’re obsessed with. The new hobby you’re failing at with enthusiasm. The conspiracy theory you can’t stop reading about. This isn’t about impressing someone—it’s about showing up as a real, curious human.

2. What Your Friends Would Roast You For

In my humble opinion, this is peak first date energy. It’s playful, self-aware, and 100% better than listing your best traits like a LinkedIn bio in disguise. Maybe it’s your inability to text back for at least 3 business days. Maybe it’s your 10-minute skincare routine or the fact that you always bring snacks to bed.  If you can laugh at yourself a little, chances are, your date will be laughing with you.

3. The “If You Know You Know” Things You Love

First dates are about connection—not perfection. So instead of listing off general likes and dislikes (we get it, you “love music”), talk about the oddly specific stuff that really lights you up. Do you quote “Seinfeld” like it’s scripture? Do you cry every time you see a dog in a sweater? Do you make PowerPoints for fun? Same.The goal: find shared weirdness. That’s where the magic happens.

4. The One Thing You Don’t Want in a Relationship

Hot take: first dates aren’t too early to talk about values—they’re the perfect time. Now, you don’t need to go unpacking your entire relationship history or trauma binder, but if something’s a non-negotiable for you, say it. If they flinch, better now than after three months of ordering pasta together in silence.

5. Your Most Dramatic “I Thought This Was a Good Idea at the Time” Story

Every great first date has at least one moment where both people are laughing with a slight undertone of well meaning concern. Enter: the personal plot twist.

Tell them about the time you tried to dye your own hair and ended up with orange roots. Or when you tried to impress someone by ordering oysters... and immediately realized you were allergic. These moments make you memorable and human. Just maybe skip the time you got back with your ex after a sound bath in Tulum. You’re healing. You’ve grown.

The Bottom Line?

A great first date isn’t about proving you're a flawless catch. It’s about showing enough of the real you to spark something that’s worth meeting again. Vulnerability. Humor. A little chaos. That's the sweet spot. And if you're using First Round's On Me, you’re already one step ahead: real dates, planned with purpose, and no endless small talk.

So go ahead—ask a better question, tell a weirder story, and remember: no one ever fell in love over “So, what do you do?” Until next time x