90 Best Flirty First Date Questions, Starters & Bad Questions to Never Ask!
Want to avoid awkward silences? These first date questions are flirty, fun, and guaranteed to spark real chemistry from the moment you sit down.
So you’re going on a first date. You’ve got your outfit, your location, your deodorant (hopefully), and now you’re wondering, what the hell do I say when the conversation hits that awkward lull?
If you’re looking for the best first date questions to spark chemistry, skip the boring small talk. Whether you want to flirt, laugh, or dive into something a little deeper, the right questions can take a first date from forgettable to unforgettable.
This isn’t a job interview, and it shouldn’t feel like one either. The secret is in asking questions that are playful, open-ended, and just vulnerable enough to create a spark.
The best first date questions for great conversation starters
Before we jump in, here’s the secret sauce:
Great first date questions aren’t about sounding smart, they’re about making your date feel something.
Whether it’s curiosity, laughter, intrigue, or a little flirty tension, the right question opens the door to emotional connection.
Psychologically speaking, conversations that include self-disclosure, sharing personal thoughts, memories, or emotions, are more likely to create feelings of closeness and attraction.
That’s why researchers like Arthur Aron created the famous 36 Questions to Fall in Love experiment, which showed that gradually deepening questions can build intense emotional intimacy in just one conversation.
📚 Source: Aron et al., 1997, The experimental generation of interpersonal closeness
Another concept at play here is Uncertainty Reduction Theory. On a first date, both people are subconsciously trying to figure out: Is this someone I’ll click with? Good questions help reduce that uncertainty by revealing values, personalities, humor, and emotional availability.
📚 Source: Berger & Calabrese, 1975, Explorations in initial interaction
So if you’re trying to create chemistry and connection, skip the robotic “what do you do?” and try questions that reveal stories, quirks, or imagination instead. We’ve organized the best first date questions into five easy sections, so you can read the room, then pick your vibe.
👉 Want to impress your date instantly? Read these first!
- 23 First Date Conversation Tips To Flirt With & Impress Your Date in Minutes
- 51 Warning Signs of a Bad First Date & BIG Red Flags in the First Few Dates
- Where to Go on a First Date: 85 Best First Date Ideas That Are Fun & Romantic
- 55 Tips & Things to Do on a First Date to Leave Your Date Smitten & In Awe!
Icebreakers & Easy First Date Questions to Keep the Flirt On
Light enough to ease in. Flirty enough to make sparks fly.
Forget the usual “where do you work?” stuff. These conversation starters are made to warm things up and build some flirty tension right from the start. Think playful, cheeky, and open-ended, the perfect mix for chemistry.
1. Do you always look this good, or is this just your “first date setting”?
Because who doesn’t love a compliment wrapped in sarcasm? Flirts, flatters, and sets a fun tone right away. [Read: 90 VERY Funny Compliments You Can Use to Flirt, Flatter & Make Them Laugh]
2. So… are you more of a “Netflix and chaos” or “Netflix and nap” kind of person?
You’ll learn if they’re a couch potato or a party gremlin, either way, it’s cute.
3. What’s your drink of choice, and how much chaos follows after the third one?
Nothing says chemistry like bonding over tequila-induced decisions.
4. What’s your go-to “I’m totally flirting with you” move? Asking for a friend.
This one is basically a flirt inside a flirt. Risky? Maybe. But that’s half the fun.
5. What’s your most irrational turn-on? Like… something weirdly specific.
This one gets people smiling and blushing. And if there’s chemistry? Game on.
6. What’s your “zero shame” guilty pleasure, food, show, or something naughtier?
A lighthearted way to peek into their quirks and test if they’re down to get a little spicy. [Read: How to Be More Playful and Flirty on Date: 18 Right & Wrong Ways To Do It]
7. So what would your friends warn me about if they knew we were out tonight?
Let them tease themselves a little. It’s always sexy when someone owns their chaos.
8. If you had to rate this date out of 10 right now, what number would get me a kiss?
Confident, bold, and cheeky. It’s a vibe-check in question form.
9. What’s something you wish more people asked you, but never do?
It opens the door to a surprising answer. Or a flirty, “You just did.”
10. How soon is too soon to make out in public? Hypothetically, of course.
Just a little tension teaser to test the waters, flirty without being cringey.
11. How much trouble do you usually get into when you say, “Let’s just have one drink”?
A great way to bond over mischief potential, and gently suggest this night might go the same way.
12. If I dared you to text your best friend something outrageous right now, would you do it?
A little playful dare adds instant fun, and you’ll learn who the bad influence is in their life. [Read: 20 Subtle Hand Gestures to Make Your Date Fall for You, Guaranteed!]
13. What’s something ridiculous that instantly gives you the ick?
Get them talking about weird turn-offs, and possibly bonding over shared ones.
14. Would you rather be famous for something amazing… or something slightly scandalous?
Gives them room to flirt, be cheeky, or say something bold.
15. If we had to roleplay any cliché first date right now, coffee shop, art museum, mini golf, what are we pretending to do?
Flirty and imaginative. It gets them visualizing “you two” in fun situations without pressure.
16. If I said I could read minds right now, what would I find out you’re thinking about me?
A bold tease. This one practically forces them to flirt back (or turn red).
17. What’s your most ridiculous dating app story?
A fun, safe space to laugh about mutual disasters and vibe over how rare a good first date feels.
[Read: Flirting: What It Is, 5 Different Types & How to Pick a Style that Works for You]
Flirty & Fun First Date Questions to Spark the Sexual Chemistry
These are the questions that stop being about what they do and start revealing who they are, the cheeky, confident, flirtatious side that turns a good date into a great one. Use these once the conversation’s flowing and you’re both vibing. Playfully test boundaries, tease, and let the sparks do their thing.
18. What’s something you’ve done that you probably shouldn’t tell me on a first date?
Instant sexual tension. Leaves just enough mystery to drive them crazy.
19. What’s one thing you’re surprisingly really good at… that I probably wouldn’t guess?
The sexy smirk they give before answering is half the fun.
20. What’s the wildest thought you’ve had during a boring meeting or class?
Innocent setup. Sinful answers. The best kind of combo.
21. What’s a random habit that might turn someone on, unintentionally?
This one sparks self-awareness and… lowkey flirting by accident.
22. Do you believe in love on first date, or should I ask you for a second date already?
Corny? Sure. Effective? Every damn time. [Read: Texting Before the First Date: 15 Rules to Make Them Eager to See You]
23. Have you ever had a crush on someone totally off-limits?
Flirty and a little dangerous. A perfect mix.
24. What’s the most PG-13 thought you’ve had about me so far?
Gets you an honest (or hilarious) answer, with a heavy dose of tension.
25. If we kissed right now, who do you think would make the first move?
You’ll know everything you need to know by how they answer. [Read: 19 Secrets to Initiate a First Kiss & Make Them Want to Keep Kissing You]
26. What’s your soft spot when someone’s trying to seduce you?
Could be a physical touch, a look, or a certain voice tone — and now you know it.
27. What’s something you’ve always wanted to try… but haven’t had the right partner to try it with?
Let their imagination go wild. The phrasing? Completely on purpose.
28. What’s your hottest dating flex, like something that would definitely make me want to see you again?
Confidence is sexy. This gives them a moment to shine, and a chance to flirt with their own charm.
29. What’s your “secret weapon” when you’re trying to seduce someone?
Gets right to the flirty fun. Plus, you’ll probably catch them smiling while imagining it.
30. What’s something totally innocent that turns you on way more than it should?
A great question for leaning into tension without going full-throttle sexual.
31. If I dared you to whisper something you shouldn’t say on a first date, what would it be?
Playful, suggestive, and bold, just make sure they’re into the vibe.
32. What’s a fantasy that sounds insane, but you’d try it if no one ever found out?
This one’s perfect if the energy is already heating up and you want to test their adventurous side. [Read: How to Get a Guy to Kiss You When You Want Him To: The Secret Moves]
33. If I told you I had a secret about you already, what would you hope it is?
Flirty and flattering, it puts them in a playful headspace and invites imagination.
34. You seem like the type that would… [insert flirty prediction]. Am I wrong?
It’s more of a setup than a question, but it’s one that invites teasing, flirting, and finding out if they’re exactly who you think they are.
Funny, Weird & Unexpected First Date Questions to Spark Laughter & Intrigue
These questions are like throwing glitter into your date’s drink, random, unpredictable, and just the right kind of weird. They show you’re playful, spontaneous, and way more fun than the usual “so what do you do?” type.
Ask these when things are flowing, or if you feel the vibe dipping and want to bring the energy back with something unexpected and hilarious.
35. What’s your most irrational fear, like, something totally harmless but you’d never admit to anyone?
We’re talking geese, escalators, or glitter. The weirder the better.
36. If your ex had to describe you in three brutally honest words, what would they say?
Spicy, chaotic, and possibly revealing, this one invites playful shade and self-awareness.
37. What would be your death row meal, and how embarrassingly specific is it?
This one always leads to laughter, cravings, and maybe even shared food obsessions.
38. If your pet could talk, what’s the first thing they’d totally rat you out for?
This one gets laughs and random confessions. Also: shows if they have pets = bonus bonding.
39. What’s the weirdest compliment you’ve ever gotten… that you secretly loved?
A great excuse to flirt by repeating it back, especially if it’s something random like “hot librarian energy.”
40. If you had to survive a zombie apocalypse with three fictional characters, who’s on your team?
You’ll learn a LOT about their humor, childhood, and who they secretly want to be.
41. What’s a ridiculous thing you believed as a kid… for way too long?
Whether it’s thinking clouds are made of cotton or that kissing gets you pregnant, this one never fails.
42. If we switched bodies for 24 hours, what’s the first thing you’d do?
Unhinged answers welcome. This one always takes a wild turn, and is very telling.
43. What’s the dumbest reason you’ve ever ghosted someone?
Laughter + petty confessions = bonding over chaos.
44. What’s your go-to karaoke song, and how dramatic do you get when you perform it?
Sets the tone for potential future date night plans… and possible karaoke flirting.
45. If you were a dating app red flag, what would your “flag” say?
A twist on self-awareness that’s charming, not cringey. Bonus points if they own it playfully. [Read: 31 Red Flags in a Man Who’s Fake-Nice & Will Only Break Your Heart]
46. What’s the weirdest lie you’ve ever told on a date, and did it work?
Because we’ve all told a tiny lie to impress someone… or escape.
47. If we were in a reality TV show right now, what would our drama be?
This one gets them to imagine the two of you as a chaotic onscreen couple. Fun, creative, and hilarious.
48. What food would immediately ruin a makeout session for you?
Garlic? Onions? Fish tacos? Let’s just say, this is valuable public service information. [Read: First Kiss Red Flags: 18 Bad Signs & What You Can Learn From a Bad Kiss]
49. If you were a flavor of ice cream, what would you be called?
Silly, sweet, and a setup for flirting: “Oh really? I’d totally taste-test that.”
50. If we got matching tattoos tonight, what would we get and where?
Unhinged? Yes. Hilarious? Also yes. Also a sneaky way to ask about their wild side.
51. What conspiracy theory do you kinda believe but would never admit in public?
Aliens? Birds aren’t real? This one can spiral in the best way possible.
[Read: 26 Things to Talk About on a First Date to Make Them Like You Instantly]
Deep & Personal First Date Questions to Stir Emotions & Spark Real Connection
Once you’ve both laughed, flirted, and gotten a little weird, it’s safe to open the door to something more real. These questions don’t feel like therapy, they feel like meaningful curiosity. Perfect if you’re vibing and want to know if this person has depth… and heart.
52. What’s something small that instantly makes you feel safe around someone?
Emotional safety is a green flag. Their answer tells you how to be one.
53. What’s a random memory that always makes you smile?
It’s nostalgic, sweet, and opens the door to a beautiful story from their past.
54. Who in your life makes you feel the most “you”?
You’ll learn who they trust, who grounds them, and what authenticity looks like to them.
55. What does “home” feel like to you, and have you ever felt that with someone?
This one gets deep fast, in the best way possible. Watch their face closely.
56. When was the last time you felt really proud of yourself?
A confidence-builder and a soft flex moment all in one.
57. What’s something you’d want in a relationship that you’ve never had before?
This reveals past pain and future hopes, perfect for reading emotional compatibility. [Read: Healthy Relationship: What It Is, 45 Signs & Secrets to Stay Happy in Love]
58. What do you notice first when you’re really into someone?
Some people say eyes. Others say how someone treats waitstaff. Their answer says a lot.
59. What’s something that used to matter so much… but now you couldn’t care less?
Reflective, insightful, and often hilarious. Growth is attractive.
60. What’s your relationship with vulnerability?
Don’t ask this unless you’re ready to go there too, but it’s a powerful one.
61. Have you ever felt seen by someone in a way that surprised you?
This one gives them space to talk about emotional connection, or signal that they want that again.
62. What’s something about you most people completely misunderstand?
A beautiful way to create space for self-revelation, and a deeper connection.
63. What’s one relationship lesson that completely changed how you date now?
Shows maturity, self-awareness, and invites meaningful insight (without trauma dumping).
64. What’s your emotional “green flag”, something that tells you you’re with someone safe?
Let them describe the kind of love they’re looking for, without directly asking. [Read: Meaning of Dating: How It Works, Types, 42 Signs & Ways to Date Someone Right]
65. Have you ever had a moment where you felt completely understood by someone?
Subtle, powerful, and emotionally charged, this one can lead to a deeper convo naturally.
66. If you could freeze one moment from your life and relive it anytime, what would it be?
A dreamy, reflective question that reveals values, nostalgia, and imagination.
67. What does intimacy mean to you, outside of just sex?
Perfect for moving into a more romantic or emotional vibe, deep without being heavy.
68. What would your ideal relationship feel like on a random Tuesday night?
This one helps you gauge alignment, but in a way that feels dreamy and cozy, not like a compatibility checklist.
End-of-Date & Future Date Questions to Leave a Lasting Impression
By the end of the night, you’ve flirted, laughed, gotten deep, and maybe even started imagining what a second date might look like. These questions are the soft landing, they signal interest, spark playful ideas, and leave your date thinking, “Damn, I want more of this.”
69. So… second date: Netflix, rooftop drinks, or something chaotic?
Flirty, confident, and gives them options while hinting you definitely want another round. [Read: How to Ask for a Second Date and Not Fumble or Appear Too Eager]
70. What’s something you’d want to do on a date, but no one’s ever suggested it?
You might get a surprise idea, and bonus, now you can be that person.
71. If tonight ended with a kiss, who’s leaning in first?
Smooth. Direct. And depending on their answer, maybe… go for it? [Read: 33 Subtle Signs to Know When to Kiss a Girl & Time the Moment Right]
72. What’s the best way to say goodbye without actually wanting to leave?
This one wraps things up with warm energy and just the right amount of flirty regret.
73. Want to make a bet on whether or not I ask you out again? Spoiler: I already want to.
A cheeky way to ask for the second date without being too serious. If there’s chemistry, this line wins.
74. If we had one more hour together tonight, what would we do?
It lets them get creative, flirty, or even romantic, and shows you’re not quite ready to go.
75. What song would be playing in the background right now if this were a movie?
It’s cute, cinematic, and helps you end the date on a sweet, romantic note.
[Read: 22 Second Date Tips & Rules to Get To Know Each Other & Fall Harder]
Red Flag Questions You Should Never Ask on a First Date
So you’ve got the charm, the outfit, and the flirting down, don’t ruin it by saying something that makes your date immediately text their group chat: “Girl, you will NOT believe what he just asked me.”
Here’s your guide to the worst first date questions, the ones that kill the vibe, raise red flags, or make you sound like you’re auditioning for a role no one wants to play.
1. How much money do you make?
Unless you’re hiring them for a job (or planning a joint mortgage?), this is an instant nope. Ask about passions, not paychecks.
2. How many people have you slept with?
Asking this on a first date screams insecurity and nosiness. Just… no.
3. Do you have any STDs?
Important eventually? Sure. Appropriate on a first date? Unless you’re planning on skipping dessert and heading straight home, definitely not.
4. Why did your last relationship end?
This is not the time to unpack ex-trauma. Let them enjoy their drink in peace.
5. When was the last time you had sex?
Congrats, you’ve just made things weird. You might as well ask, “How desperate do I sound right now?”
6. Do you think you could love me?
Sir. Ma’am. Please. It’s the first date, not a Nicholas Sparks novel.
7. Are you planning to have kids?
It’s giving interview for life partner way too soon. Let’s at least finish the appetizer first.
8. How old are you again?
This one can be okay if it comes up naturally, but if you say it with squinting suspicion? Red flag alert.
9. Do you always look different in person?
If you want a second date, maybe don’t start by negging them. Compliment instead.
10. So… are you emotionally available right now?
Genuinely sweet question, just way too soon. First, check if they’re snack-available.
11. Would you ever consider a threesome?
Unless your first date was scheduled after 2AM, this will come across as sleazy, not sexy.
12. Are you seeing anyone else?
If it’s a first date, assume they are. You’re still auditioning. Don’t panic, impress instead.
13. How much do you weigh?
This isn’t the DMV. There is never a reason to ask this. Ever.
14. Are you close to your ex?
We’re not starting a relationship based on jealousy. It’s weird and controlling. Skip.
15. What’s your biggest trauma?
We said deep and personal, not therapy on the rocks. Save the heavy stuff for date three or, ideally, your therapist.
[Read: First Date Nerves: 22 Secrets to Not Be Nervous & Feel Relaxed On a Date]
Pro tip:
If you wouldn’t want someone asking you the question, or if it makes your friends raise their eyebrows when you rehearse it in the mirror, don’t ask it.
The best first date questions are curious, kind, and flirtatious, not prying or invasive.
The most important thing to do on a first date? Relax!
Now you have plenty of first date questions to use throughout your conversation. It’s good to know that you have these questions in your back pocket in case the conversation starts to stall. That should give you confidence.
However, the most important thing you should do is just to chill out and relax. By doing that, you’ll be able to just be yourself and allow your wonderful personality to shine through. When you do that, your date will be so charmed, they’ll want to arrange a second date.
[Read: Strong Feelings after a First Date? How to Read All the Right Signs]
Use as many of these first date questions as you can squeeze in casually, mix in your natural charm, and trust me, they’ll already be thinking about date number two.
