What to ask a girl: 100 questions for any stage of dating

You’re mid-conversation with a girl you like, and your brain just goes blank. You scramble for a topic, land on the weather, and instantly regret it. Somewhere between “how’s your day going” and dead silence, you’ve run out of things to ask. It happens to almost everyone, even guys who think of themselves as good talkers.

This list is the fix. A hundred questions to ask a girl, split into ten topics, so there’s always somewhere new to steer the conversation. Some of them are light enough for a first date, some dig into what she actually wants out of life, and a few exist purely to make her laugh. Use them on the phone the first week, three dates in, or two years into a relationship — they work at any stage, whenever the talk needs a nudge. None of them need a script, and you can read straight off this list if you have to.

1. Hobbies and interests

1. When you’re bored, sad, or just feeling off, what’s the first thing you do to shake it, and does it actually work?
2. If money were no object and some hobby could pay your bills, which one would you pick over what you do now?
3. After a rough day, do you want to be around people, or do you just want to be left alone — or does it depend on how bad the day was?
4. If you’d gone pro in a sport, which one would it have been, and do you still play it for fun?
5. Would you call yourself more of a thrill-seeker, or someone who likes to slow down and think things through?
6. What’s a birthday gift that would actually mean something to you, and why?
7. Given the choice between a concert, a dance show, an art exhibit, or a movie night, which one wins?
8. Is there a country that just feels like “you,” even if you’ve never been there? What’s the pull, and what do you actually know about it?
9. Dogs, cats, or something wilder — what’s your favorite animal, and what would you name it?
10. What’s a hobby you’ve always wanted to try but never found the time or the chance to start? What’s stopping you now?

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2. Personality and habits

1. What’s the one quality about yourself you’re proudest of?
2. If you could delete one trait of yours and swap in a new one, what would you pick, and what would replace it?
3. How hard is it to actually make you angry, catch you off guard, or hurt your feelings?
4. Do you have any habits you’re not proud of — swearing, biting your nails, cracking your knuckles — and any idea where they came from?
5. Are you a planner, or do you just figure it out as you go?
6. What’s guaranteed to make you smile or crack up, no matter your mood?
7. You find a suitcase full of cash on the street. Are you thrilled, shocked, or immediately suspicious, and what do you do with the money?
8. Describe yourself in exactly three words.
9. Do you get more out of giving gifts or getting them?
10. If your kids ended up with your exact temperament, would that be a good thing? What would you want to change?

3. Friends and family

1. How did you and your best friend actually meet? Did you get along right away?
2. Does your family have any traditions, and is there a new one you’d want to start yourself someday?
3. Are your friends all similar to each other, and what do you think connects you to them?
4. Could you be close friends with a guy, or do you think men and women can’t really pull that off?
5. Tell me about your family — what are your parents like, any habits or quirks that stand out?
6. Who in your family are you closest to, and why?
7. What does someone have to be like to earn a spot as your friend, once you actually let them in?
8. If people who know you only described you to a stranger, what do you think they’d say?
9. Is there something about your family that makes it different from everyone else’s?
10. Growing up, did your family say “I love you” a lot, hug, kiss goodbye — or was that just not how your family showed love to each other?

4. Serious questions

1. What does your ideal family look like — how many kids, who calls the shots, how close and openly loving is everyone?
2. Could you live in another country long-term, or would you always want to stay close to home? What would change your mind?
3. How much does it matter that a partner shares your religion? Would you ever convert for someone you loved?
4. Where’s the line for cheating, for you — does it start at sex, at a kiss, or even just flirting and thinking about someone else?
5. If your husband could fully support you financially, would you still want to keep working?
6. Do you think the right couple is just fate, or two people who choose to keep working at it?
7. Besides cheating or abuse, what could actually end a relationship for you? What would be the final straw?
8. How much do you expect a guy to handle around the house, and how much would you take on yourself?
9. Could you date someone who’s genuinely popular with other women, or would the constant attention start to get to you?
10. If a guy lost his job and just couldn’t find another one, no matter how hard he tried, how would you react?

5. Questions about relationships

1. What traits does a guy absolutely need to have if he’s going to be your husband someday?
2. What flaws in a partner could you actually live with, and which ones would wear you down over time?
3. How do you act during a fight, what usually starts them, and who ends up apologizing first?
4. Do you like getting compliments, and do you give them yourself? What kind, and how often?
5. When it comes to splitting chores, do you like taking turns, splitting things along “his and hers” lines, or doing everything fifty-fifty?
6. Can you talk straight about feelings and problems, or do you tend to hint and hope he picks up on it?
7. What actually makes a relationship “serious” to you — sex, how long you’ve been together, how close you are, or something else?
8. Would you introduce a guy you’re seeing to your friends early on, or take your time before you do that?
9. How jealous are you, honestly? Would it bother you if he hung out with his friends without you a couple of times a week?
10. How much does a guy’s income matter to you? Could you date someone who makes less than you do?

6. Thinking about the future

1. Do you actually like what you do for work, or could you see yourself doing this for the rest of your life, or is it just paying the bills for now?
2. When do you picture yourself getting married and having kids, and would you rather just move in together, have a simple legal ceremony, or go all out with a big religious wedding?
3. How different do you think your life will look five years from now?
4. Do you have any goals you’re chasing that’ll take more than a year to reach?
5. Is there a class or course you’d want to take, just to grow — professionally or personally? What would it be?
6. Is owning your own place, or your own car, something you’re actively working toward right now?
7. When you picture raising kids, are you following some method, copying how your parents did it, winging it as you go, or just trusting your gut?
8. Got any travel plans for the next ten years? Where, and what’s the pull?
9. Do you picture your future as one big household — parents, kids, grandkids all together — or just you, your partner, and your own kids?
10. How long does a guy usually have to know you before you’re ready to meet his family, or move in together?

7. Stories from her past

1. What’s your warmest memory from childhood, the one you go back to without even trying?
2. Do you remember your first kiss, or your first real relationship? Would you tell me about it?
3. What were you like as a kid, and as a teenager? What did you dream of becoming back then?
4. Do funny, weird things happen to you a lot? Give me a couple of your best stories.
5. Is there a smell, a song, a place, anything that hits you with nostalgia out of nowhere? What’s the story behind it?
6. What old songs or movies do you still love, and will probably still be listening to or watching in ten years?
7. Did you actually like school? What was the best part, and what did you dread the most?
8. When were you the most scared, or the most embarrassed, you’ve ever been in your life?
9. Was there ever someone you were really close to, and you just drifted apart? What happened, and would you want to reconnect?
10. If you could write a letter to yourself from ten, fifteen, twenty years ago, what would you say, and how much do you think it would’ve changed things?

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8. How she sees life

1. When something goes badly wrong, do you dwell on it for a while, or bounce back fast?
2. How much does unfairness get to you? Have you ever actually stepped in for someone who got a raw deal?
3. Is your first instinct to look for the upside in a bad situation, or to immediately worry about what could go wrong?
4. How religious are you? Do you believe in something bigger stepping in, whether that’s punishment, miracles, or blessings?
5. Do you think life needs a plan, or is going with the flow and living for today the better approach?
6. Would you call yourself a happy person overall? What makes you say that?
7. Does your life feel harder than most people’s? Do you feel like you’ve had more to push through than average?
8. Do you love meeting new people and getting close fast, or do you keep a small circle and guard your alone time?
9. Do you believe you really have to try everything in life at least once, even the stuff that scares you?
10. What’s something in your life you’re genuinely grateful for?

9. Flirty and spicy questions

1. Be honest — would you look good in one of my shirts, and would you actually wear it out?
2. What’s the sexiest thing about you — a body part, or something about your personality?
3. Do you have any little rituals you always do before or after sex, even small ones?
4. Would you ever agree to be in a movie that required getting partially, or fully, naked, for the right role?
5. Do you think you could win a guy over with just one look? Want to try it on me right now?
6. Do you believe aphrodisiacs actually work? Have you ever felt one kick in?
7. Does good lingerie make you feel more confident, even hidden under your clothes where no one can see it? What kind works best for you?
8. Have you ever planned out the perfect night — the kind that has a “continuation”?
9. Could you write an 18+ book, or a comic, starring the two of us?
10. Have you ever had sex you seriously regretted afterward, and looking back, what would you have done differently?

10. Just for laughs

1. If I dyed my hair pink and started wearing Barbie T-shirts every day, would that be a dealbreaker?
2. Realistically, how many years would I have to wait in Azkaban before you’d agree to kiss me?
3. If I were a Pokémon, out of all of them, would you actually pick me?
4. Do you ever see a stray puppy and just want to take it home? (Woof woof, by the way — that’s me trying to get adopted too.)
5. Honestly, what’s not to love about a guy this generous, noble, handsome, brave, and humble? Take your time, I’ll wait.
6. What would I actually have to do to impress your third cousin twice removed, the one you barely talk to?
7. If I forgot your hamster’s — or your puppy’s, or your cat’s — birthday, how far and how fast would I need to run?
8. Can I kiss you right now, and then slap myself for being that bold?
9. If I 3D-printed a copy of you, would you be okay with me doing some fairly indecent things with it?
10. If this doesn’t work out between us, are you at least cool with me still showing up to watch football with your dad?

That’s a hundred ways to keep a conversation alive, whether you need to fill an awkward silence or actually want an answer to something you’ve been wondering about her. Some of these are just for fun, some get pretty deep — pick whatever fits the moment you’re in. You don’t have to burn through all hundred in one night; save some for next week, and for the week after that. Ask a few, listen to the answers, and you’ll end up closer to her, and remembered as the guy who’s genuinely easy and interesting to talk to.

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