Try this one tonight. "What street did you grow up on, and which house would you point out first?"
Small and specific beats deep and vague, at least at the start. The good questions to ask your girlfriend leave a door open for a second one, and the second one is where you learn things. Say she mentions the house two doors down with the scary dog. Drop whatever you planned to ask next and find out what the dog was called.
Easy openers for a third date
Third dates tend to happen somewhere loud, like a ramen counter where you both end up facing the cook instead of each other. That helps. Sitting shoulder to shoulder, she can think without you watching her think, and most of these can be answered between two bites. Ask the broth one before the bowl is empty.
- What was the first concert you ever went to?
- Do you drink the broth at the end?
- Which bookstore aisle do you drift to when you're killing ten minutes before a movie?
- How many alarms does it take to get you out of bed?
- Is there a store you can't walk past without going in?
- Who taught you to ride a bike, and did they let go too early?
- Window seat or aisle seat, and why?
- At a museum, do you read every little sign next to the paintings or keep walking?
- What's the best thing you've ever eaten standing up?
- Has a book ever kept you up way past the point of being sensible?
- If you could be instantly good at one party trick, which one?
- Sweet or savory breakfast on a Saturday?
- Did you have a nickname at school, and am I allowed to use it?
Window or aisle is a better third-date question than it has any right to be, because nobody picks a seat without a reason. The concert question looks quick and rarely is. If she names a band you've never heard of, ask her to play you one of their songs, quietly, right there at the counter.
Remember whatever name she gives for the bike question, since that person will come up again. She might refuse to share the school nickname. Ask again around date ten, when she trusts you not to use it in front of her friends.
Cute questions to ask your girlfriend under one blanket
Do you think we'd have been friends in middle school?
Expect a quick yes or a long, very detailed no. The no is better. Cute questions work once you've got a little history to poke at, and they're best under one blanket while you both pretend not to fight over it. Most of them go fast.
- Which side of the couch is yours, and when did you decide that?
- If we opened a tiny restaurant together, what would be on the menu?
- Was there a moment on one of our early dates when you thought, oh no, I like this one?
- Have you kept anything I gave you?
- What would our band be called, and which of us is the drummer?
- Is there a song that makes you think of me, even a slightly cheesy one you'd never admit to in public?
- Which of my friends did you like first, and which took longer?
- Do you know my usual order by heart yet?
- Where would we go first if we left tonight with one bag each and no plan past the airport?
Take your time with the song question. If she picks something cheesy, wait a week before you tease her. And have your own answer ready for the early-dates one, because it's coming right back at you.
The keepsake one is quick unless she says yes. Then ask where it is, and keep a straight face if it's a ramen receipt. The band one is nonsense on purpose. Fight about the drummer.
About the family she grew up in
Family questions get long answers, and sometimes a pause before them. Some families are hard to talk about, so if one of these personal questions to ask your girlfriend gets a two-word reply, drop it and jump to the dog one.
Leave out the census stuff, too. She'll mention how many siblings she has on her own. You'll learn more from the house rules and from whatever hung on the fridge under a dentist's magnet.
- Who in your family tells the same story every holiday?
- What rule in your house did you assume every family had, until you slept over at a friend's?
- Was there a cousin or a neighbor kid who got you in trouble, even when it was their idea?
- How did your family do birthdays?
- What was on the fridge door when you were growing up?
- At family parties, were you the loud kid or the one on the stairs watching everybody?
- If your family had a motto nobody ever said out loud, what would it be?
- Did you grow up with a dog, and what did it steal off the counter?
The sleepover one usually runs long, and it's funnier than she expects. On the fridge question, follow up with what stayed up there longest. Hang on to the birthday answer. When hers comes around, you'll know whether she wants a fuss or a quiet dinner. The motto question takes a minute, and if she answers too fast, ask who at home would disagree.
Late-night deep questions to ask your girlfriend
On a late train home, with six stops left and the car nearly empty, there's room for a question that needs a minute. Ask one. Her first answer might come fast. After a look out the window, she may come back with the one she means. Let the silence sit. If you need somewhere to put your eyes, read the route map above the doors.
- What does a good, ordinary weekday look like for you?
- Which compliment has stuck with you the longest, and who said it?
- When did you last surprise yourself, in a good way or a bad one?
- Do you think you're more like the person you were at ten or at twenty?
- Who knows you best right now?
- Is there a life you picture sometimes, where you took the other job or stayed in the other city?
- How can you tell you need a day alone, before anyone else notices?
- What's a question you wish people asked you more often?
- If you could relive one afternoon from this year exactly as it was, which one?
- Have you ever kept a promise that cost you something?
- Where do you feel most like yourself, and when were you last there?
- Are you easier on other people than you are on yourself?
- Did someone say something to you this year that you're still turning over?
- Whose opinion of you matters more than you'd like it to?
- Which goodbye in your life do you still think about?
The weekday question looks like small talk, then turns into her whole week. When she quotes a compliment word for word, ask whether the person who said it knows it stuck.
Asking who knows her best takes five seconds and can fill an hour. If she names a person, ask what they know about her that you haven't figured out yet. Save the goodbye one for a night with nowhere to be.
What she's working toward, and what scares her
If every job paid the same, what would you do all day?
It's quick to ask and slow to answer. Try it somewhere you're both sitting still, like a museum bench or the top of a hike once you've caught your breath. Ambition is the easy half of this set. The fear questions take longer, and she might want to answer one of those on a different night.
- Which job did you want at nine, and what happened to it?
- What part of your work makes the hours disappear?
- Whose career would you steal for a week?
- Is there a skill you have that nobody at work knows about?
- How much of where you are now did you plan, and how much just happened?
- Where do you want to be living at forty, and who lives next door?
- Do you get Sunday-night dread, and what's it about?
- Can you remember the last time you were scared in a good way?
- Have you ever turned something down out of fear and wondered about it later?
- What's the worry you carry around most days, if you don't mind saying it out loud?
If she says astronaut to the first one, ask what changed her mind, and whether part of her still checks the launch dates. For the career one, ask which part of that person's week she'd skip.
When the Sunday-night answer is a person instead of a task, ask how long that's been going on. The worry question is the heaviest on this page. Ask it once, and if she brushes it off, believe her.
Funny and random ones for the laundromat wait
Nothing here runs long. After the worry question you'll both want something silly, and any of these fits inside a forty-minute dryer cycle with time left to fold. Take turns. Whoever loses the plane-clapping argument carries the basket to the car.
- Which dryer in here looks like it has the worst personality?
- Is it acceptable to clap when a plane lands?
- If a pigeon followed you home, what would you name it?
- What's the most useless thing you know by heart?
- How would your friends describe your dancing, in one word?
- Weirdest place you've ever fallen asleep?
- Would you survive a week as a substitute teacher for a room full of twelve-year-olds who know you're new?
- Have you ever waved back at someone who was waving at the person behind you?
- Can you guess what the person at dryer four does for a living?
- If you had to rename the moon, what would you call it?
- Out of everything in your kitchen, what's the thing you should've thrown away a year ago?
- Who in your life would ruin a surprise party within an hour of hearing about it?
The dryer-four one can turn into a twenty-minute backstory for a total stranger, complete with a name. Give them a job and a secret, then move on to the moon question before anyone catches you staring.
Questions for couples where you both answer
Saturday mornings at the farmers market come with a bread line that barely moves, usually because someone up front wants to taste every jam. That's your window. Whoever asks has to answer too, and goes second. It's the hard seat, since you can't borrow the first answer.
- Who do you think fell first, and when?
- Which of our dates would make the worst movie, and who would play us?
- Do we have an inside joke that would take ten minutes to explain to anyone else?
- How do we each act when we're hungry?
- What did each of us get wrong about the other on our first date?
- Where should our next trip be if we each get one veto?
- What's a rule we follow that we never actually agreed on?
Who fell first usually gets two different answers, both delivered with total confidence. The hungry one is quick, and you'll both point at each other. Ask the veto question with a map open and you might have a trip half planned before the bread line moves. For a set with right and wrong answers, these couple quiz questions test how well you know each other.
For a long-distance video call with bad wifi
You still there, or did the wifi eat my last question?
Calls freeze, and long answers get chopped into pieces. The long-distance questions to ask your girlfriend that hold up best are short, and a few get her to turn the camera around. After each one, wait for her face to catch up with her voice before you follow up. If it's already dark where she is, save the window question for a weekend morning.
- What's outside your window right now, and can you turn the camera around?
- Did you eat anything today that I'd be jealous of?
- Is there something on your desk that I've never seen before?
- Which thing in your room would you grab first if you had to fly here tomorrow with one carry-on?
- If I were there tonight, where would we walk after dinner?
- How many days until we're in the same room, and what do we do first?
Write down her answer to the carry-on one before you mail the next package. The countdown question is quick and a little sad. When the call ends, send her a miss-you card, which tallies the days since you were last in the same room and tucks away four short letters she can open when the next call feels far off.
Making a game of it
Sometimes a question goes down easier with a game around it. The photo puzzle card scrambles one of your photos into sliding tiles. When she's slid the last tile home, she reads your message, and after it come the questions you've added for her to answer. Add a couple of the cute ones she hasn't heard yet. The love language quiz is one to take together, since it compares your results as a couple. Then it's her turn. She can ask back from these questions to ask your boyfriend.
Frequently asked questions
Which questions should you avoid early on?
Hold off on exes, money, marriage and kids until she brings them up herself. Asked too soon, they can feel like a test she never agreed to take, even when you mean them kindly.
Is it weird to read these off your phone?
On a date, a little. Pick two or three before you go and keep them in your head. On the couch it's fine, and she'll probably grab the phone to pick the next one herself.
Can you send these over text?
Yes, and the cute and funny ones work fine as texts, best in the evening when she has time to type more than one line. Save the deep ones for a call or a walk, where she can hear that you're still listening while she thinks.
Do these still work after a few years together?
Yes, because answers change. Ask the one about where she wants to live at forty again next year, and compare it with what she said this time.