70+ First-Date Questions to Keep the Conversation Moving

Updated on Oct 3, 2025 at 8:45 AM

In the hours leading up to a first date, there's a good chance you might feel a sort of buzzy, nervous energy. This could be because you're overthinking how the date will go (stop that!), but it could also be because you're racking your brain for some easy — but flirty — first-date questions.

While pre-date rituals like journaling or working out can do wonders to calm the anxiety beforehand, you might also find that having a list of first-date questions handy can help keep the nerves at bay during the actual meet-up. Those questions are an easy fallback when you find yourself stuck in a moment of awkward silence, and they're a great excuse to get to know your date even better.

Whether the small talk is winding down, you've reached a bout of awkward silence, or you're not ready to say goodbye just yet, we've compiled over 70 one-liners that make for perfect first-date questions. There are ice breakers, funny questions, and would-you-rather prompts for when you want to keep things light and fun. (But if you want to kick it up a notch, you could also advance to these saucy questions to ask your crush instead.)

Whenever you're ready to learn just a little more about the cutie seated in the barstool next to you, give one of these first-date questions a spin and let the chemistry flow.

Funny First-Date Questions

Every first date needs a silly question or two. The following can help you each relax and lighten the mood. Best paired with a coy smile or a cheeky little wink.

What's your best dad joke?
What's your cheesiest pickup line? I want to see if it actually works.
What's your worst first-date story?
On a scale of 1 to nightmare, how embarrassing was your first kiss?
What was the weirdest thing your younger self did?
What's the most embarrassing thing you've done on a date?
What nicknames do your friends and family call you?
What's the most outrageous lie you told as a kid?
If you had to go on a reality dating show, which would it be and why?
What show or movie do you quote the most?
What are your go-to memes?

Important First-Date Questions

Sometimes you have to swap the small talk for some important first-date questions that will help you decide whether you actually want to see this person again. The following questions are just the right amount of earnest, but won't make you come off as too intense.

What's something you've accomplished that you're really proud of?
Who are you closest to in your family?
What would your best friend say are your biggest strengths and weaknesses?
Why did you decide to move to this city/town?
Are you an introvert or an extrovert?
What's a big life goal of yours, and what do you need to make it a reality?
Where or what makes you happiest?
What's one of your favorite childhood memories and why?
If you had a whole day to yourself, how would you spend it?
What do you love most about your job?
What qualities do you look for in friends?
What's something you're excited to experience in the future?

Ice-Breaker First-Date Questions

Sometimes, first dates start off a little tense — it's scary to put yourself out there! To help relax, try some of these ice-breaker first-date questions that will move things along.

What's the quirkiest thing about your hometown?
What's your go-to karaoke song?
What's your most recent "pinch me" moment?
If you had to give a TED Talk tomorrow, what would be the topic?
What show do you put on at night to help lull you to sleep?
What's your favorite vacation spot?
What are your pet peeves?
As a kid, what job did you think you'd have as an adult? And what job did you want?
If you won the lottery tomorrow, how would you spend the money?
What book is on your nightstand?
What are your go-to recommendations for TV shows, movies, and books?
Are you a morning person or night person?
Are you a beer person or wine person?
Do you have anything on your bucket list you've been dying to check off?
Are you a pet person or a plant person?

Flirty First-Date Questions

If the chemistry is there and you're feeling all the things, asking your date a flirty first-date question might be the move. Just be sure to read the room first!

How do you feel about kissing on the first date?
Did you believe in soulmates before this date? How about now?
What kind of hugger are you?
Who's your celebrity crush?
What's the first thing you noticed about me?
What's the riskiest place you've fooled around with someone?
How do you feel about PDA?
Do you think opposites attract?
What do you find most attractive in somebody?
What's the craziest sex dream you've ever had?
So, what are we doing after this?
When can I see you again?

Serious First-Date Questions

To know if you're actually compatible, you may have to broach some more serious topics. Mix some of these in with your other fun and flirty questions to get a sense of where their head is at.

What do you think makes you unique?
What are you looking for right now?
What are your relationship deal-breakers?
What does a relationship look like and mean to you?
Are you focused more on career or family right now, or both? Neither?
What's a social issue you're passionate about?
What's your relationship to religion?
How did your family shape you into the person you are today?
Whose opinion do you value the most?
Who do you go to when you need career, financial, relationship, or life advice?
How do you view marriage?
Do you ever think about what kind of parent you'd be?
What does your dream home look like?
When do you know you're falling for someone?

Would-You-Rather First-Date Questions

When in doubt, pull out a would-you-rather first-date question. At the very least, you're bound to learn something interesting.

Would you rather go to a nice restaurant or get takeout for an anniversary dinner?
Would you rather know your partner's complete dating history or nothing at all?
Would you rather get a good-morning or a goodnight text?
Would you rather only text or only talk on the phone?
Would you rather go on three mini staycations or a week-long destination vacation?
Would you rather meet your favorite actor or your favorite music artist?
Would you rather go on a date with your most recent ex or the person you lost your virginity to?
Would your rather date a relative's ex or a friend's ex?
Would you rather give up sex or your favorite food?
Would you rather be handcuffed or blindfolded?
Would you rather have sex in a car or an airplane?
Would you rather accidentally send a nude photo to your parent or post it to your Instagram Story?

— Additional reporting by Taylor Andrews

Emily Weaver is an entertainment and lifestyle contributor for PS. Her writing focuses on celebrity relationships, movie and book news, and product shopping guides. Her bylines include PEOPLE, Real Simple, Better Homes & Gardens, HelloGiggles, Scary Mommy, and more.

Taylor Andrews is the senior balance editor at PS, specializing in topics relating to sex, relationships, dating, sexual health, mental health, travel, and more. With eight years of editorial experience, Taylor has a strong background in content creation and storytelling. Prior to joining PS in 2021, she worked at Cosmopolitan.