12 Fun and Sexy First-Date Questions

A first date is the perfect place to take your chemistry to the next level. And when you’re as focused on what comes out of your mouth as what you’re putting in it, having a roster of first-date questions on deck will guarantee the night doesn’t finish prematurely.

No matter how deep you’re looking to go, these conversation starters won’t just break the ice — they’ll evaporate it. The right questions will help you avoid awkward silences, make a positive first impression, and pave the way for a second date. Think of it this way: The only place small talk should come before penetration is at the proctologist’s office. Save the surface-level chit-chat for the water cooler and get ready for the must-ask questions for your next first date.

1. What’s your beverage of choice?

This is a fantastic question to kick things off with because his order will give you some keen insights into who he is. Negroni sbagliato with prosecco? That’s a twink. Pappy Van Winkle? We got a sugar daddy on our hands. A shot of Jäger? Yeah, he’s been pegged by a girl before. And if he orders a Tito’s dirty martini — douche accordingly.

2. If you were a drag queen, what would your drag name be?

A playful question makes a perfect icebreaker while you’re waiting for that first cocktail to kick in. Is he a Sasha Colby, Jinkx Monsoon, or Tammy Brown? Drag art is arguably the mother of all forms of self-expression, so you’ll learn a lot about his best (and worst) qualities when he unleashes his inner queen.

3. What’s your go-to karaoke song?

Whether it’s Rihanna, Nirvana, Radiohead, or Cher, his answer here will give you insight into his musical taste — and his personality. If you’ve got a Madonna, he stays loyal. Drake? He thinks he’s much smoother than he really is. Is he a Britney, bitch? Enjoy the show, but be ready to protect his fragile heart. And if he says Doja Cat, follow him to the party, ’cause he’s got his finger on the pulse.

4. What’s your guilty pleasure TV show?

Does he drool over the designer clothes on Selling Sunset or the deckhands on Below Deck? Trashy television is as restorative as a mobile IV after a night out in West Hollywood, and his take on Scandoval will tell you all you need to know about his boyfriend potential.

5. What’s your favorite book?

By this point in the conversation, you should have a feel for his interest in mental stimulation. Maybe the only thing he reads regularly are the video descriptions on BukkakeBoys, and that’s okay — just ask about his favorite movie or podcast instead. If the question seems to put him on the spot, make it easier by asking about the best film he’s seen recently or the last book he read. You can also offer some recommendations to gauge his interest in exploring the media you love.

6. What’s your biggest pet peeve?

If you spoon in your sleep and he cringes at the thought of postcoital cuddles, you might want to bow out now before becoming the featured victim on an episode of Snapped. But if what bothers him most is a partner who leaves the poppers open between sniffs and it’s a bad habit you know you’re able (and willing) to break, keep the conversation going. And start putting the cap back on, you wasteful bitch.

7. Who’s your celebrity hall pass?

No matter what kind of rules you and your long-term partners typically live by, it’s fun to lust over celebrities together, and you can quietly (or openly) judge his fantasies and what they say about him. Does he dream of getting dicked down by Idris Elba? He’s clearly a man of culture. Has the hots for Tom Hardy à la Mad Max? He’s into bondage. Wants to tap Justin Trudeau’s maple tree? Us too, eh.

8. What’s the wildest thing on your sexual bucket list?

Speaking of sexual fantasies, which dreams can you actually help him achieve? Sex on a plane? Doing the Eiffel Tower in an elevator? Doing the Eiffel Tower in the elevator of the Eiffel Tower? Whether your lists have a lot in common or leave each other with your jaws on the floor, this question will show you where he falls on the adventure spectrum and how much bail money you need to save up if you plan on spending much time with him.

9. What’s the most embarrassing thing that’s ever happened to you?

The answer here could be funny, but it might be mortifying, so read the room and take care not to laugh at a story that caused him pain. And if you ask this question, be ready with an answer of your own — or better yet, come prepared with two. If he makes you cry laughing, telling you about the time the TSA flagged him for his Reno Gold Fleshlight, offer up a funny story in return. If the tale he tells leans more toward the traumatic side, reciprocate his vulnerability and tell him an embarrassing story that still haunts your dreams.

10. What’s your hidden talent?

What weird thing is he secretly good at, and what does it tell you about him? If he can solve a Rubik’s Cube in under five seconds, he’s smart (and probably good with his hands). Knows how to say “good boy” in 50 languages? ¡Qué caliente! And listen, if watching him tie a cherry stem in a knot with his tongue doesn’t make you quiver, pass the peach to someone who can appreciate his skills.

11. What’s your kinkiest kink?

Kink compatibility is as important for one-night stands as it is for long-term lovers. If his hottest turn-on makes you want to run for the hills, one of you will always be either unfulfilled or pretending to be comfortable with something you’re not. No kink-shaming here — just listen and share to see how you two align. If he’s vanilla and you’re all about the watersports, there might be roadblocks in the bedroom that are hard to overcome. Chances are those issues will eventually bleed into the nonsexual parts of the relationship (if it ever even gets that far).

12. Where’s the most scandalous place you’ve ever had sex?

On a backhoe with the landscaper? On Grandma’s water bed with his cousin’s Brazilian exchange student? You’re both bound to have some stories, but if the answers here are anti-climactic, turn the date into a brainstorming session and add some creative hot spots to your mutual bucket list.

Just the tip(s)

Think of this list as a source of inspiration, not a script. Nothing kills a hard-on faster than a man who lacks confidence. So relax, let the conversation flow, and keep your phone in your pocket and your eyes on him.

We’ve got a few more tips to make sure you don’t start sweating too soon:

• Listen to his answers. Don’t jump from question to question like you’re conducting a job interview. He’s likely to offer up some interesting responses, so let him speak, be an active listener, and ask follow-up questions to show him you genuinely care about what he has to say.
• Be ready to answer back. If you’re doling out the best questions he’s ever heard on a first date, be ready for him to turn them right back on you. Prep some clever responses, and skip any questions you wouldn’t feel comfortable answering yourself.
• Don’t ask about his past relationships, and…
• Don’t talk about your past relationships. There’s no room for exes on a first date. You can share the gory details later if things get serious, but bringing it up now will suggest you’re hung up on the past — and honey, that’s always a red flag.
• Speaking of red flags, pay attention to his body language. If he looks uncomfortable, change the direction of the conversation. And if you start squirming, remember that you’re free to exit stage left whenever you damn well, please.