78 Questions to Keep the Convo Going on a First Date
In the hours leading up to a first date, there's a good chance you might feel a sort of buzzy, nervous energy — a combination of nerves and excitement as you picture how the date will go. You might even be asking yourself, what do I wear? Where should we go? Will they like me? Am I about to meet my soulmate? And a million other things.
Though pre-date rituals are helpful, you might also find that having a handy list of first-date questions can help keep your (and your date's) nerves at bay. Having some questions ready ahead of time is a great fallback when you find yourself stuck in a moment of awkward silence, and it's a great way to help you 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 pooled together over 75 questions that make for perfect first-date banter. There are ice breakers, funny questions, and would-you-rather prompts for when you want to keep things light and fun. Or, if you're feeling shy or nervous about making a move, we've gathered some flirty questions as well.
For those who want to dig a little deeper and form a more solid connection with their date, here are the best first-date questions for whatever vibe you're going for.
— Additional reporting by Taylor Andrews
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Funny First-Date Questions
- What's your best dad joke?
- What's your cheesiest pickup line, and does it actually work?
- What's your worst first-date story?
- What's the story behind your first kiss?
- What's the most embarrassing 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 craziest lie you told as a kid?
- If you had to go on a reality dating show, which would it be?
- What show or movie do you quote the most?
- What meme do you refer to the most?
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Important First-Date Questions
- What's something 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 or town?
- Are you an introvert or an extrovert?
- What's a big life goal of yours?
- Where or what makes you happiest?
- What's one of your favorite childhood memories?
- If you had a whole day of nothing planned, how would you spend it?
- What do you love most about your job?
- What do you love most about your friend group?
- What's something you're excited to experience in the future?
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Ice-Breaker First-Date Questions
- What's the quirkiest thing about your hometown?
- What's your go-to karaoke song?
- What's your best "pinch me" moment?
- If you had to give a TED talk tomorrow, what would you talk about?
- 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?
- If you won the lottery tomorrow, how would you spend the money?
- What book is on your nightstand?
- What are your go-to TV show, movie, and book recommendations?
- 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 cat person or a dog person?
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Flirty First-Date Questions
- How do you feel about kissing on the first date?
- Do you believe in soulmates?
- 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?
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Serious First-Date Questions
- 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 more focused on career or family right now?
- What's a social issue you're passionate about?
- Were you raised in a religious household?
- How has your family and upbringing shaped 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'll be?
- What does your dream home look like?
- When do you know you're falling for someone?
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Would-You-Rather First-Date Questions
- 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 be in the dark?
- Would you rather get a good-morning or a goodnight text?
- Would you rather only text or 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 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 be able to see your future or your significant others?
Dirty Would-You-Rather Questions:
- Would you rather give a lap dance or get a lap dance?
- 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?