Questions to Ask Your Boyfriend

Easy questions to get him talking

Low-pressure questions for a car ride, a queue, or the first few weeks of dating. None of them need a big answer, but most of them get one.

1. 1What's a food you hated as a kid that you'd eat now without thinking about it?
2. 2What do you order when you can't decide what you want?
3. 3Which app on your phone would be the most embarrassing to show me your screen time for?
4. 4What's the last thing you bought that you were genuinely excited about?
5. 5If you had a free Saturday with no plans and no phone, what would you end up doing?
6. 6What song do you skip every time, no matter what mood you're in?
7. 7Which of your friends would you call if your car broke down at 2am?
8. 8What's a small thing you're weirdly good at?
9. 9What's a chore you don't mind doing, and one you'll put off forever?
10. 10Who's the most famous person you've ever been in the same room with?
11. 11What's a show you've rewatched more times than you'd admit?
12. 12What's the best meal you've had in the last year, and where was it?

Questions about growing up

Childhood questions are the fastest way to understand why he is the way he is. Ask them slowly and follow the stories wherever they go.

1. 13What did your family do on a normal Sunday when you were ten?
2. 14Who was the adult you looked up to most as a kid who wasn't one of your parents?
3. 15What did you get in trouble for most often?
4. 16What did your bedroom look like when you were a teenager?
5. 17What's a rule in your house growing up that you thought every family had?
6. 18Was there a job you wanted as a kid that you'd still secretly like to try?
7. 19What's the first thing you remember saving up money to buy?
8. 20Which teacher do you still think about, good or bad?
9. 21How did your parents argue, and how did they make up?
10. 22What's a family tradition you want to keep, and one you'd quietly drop?
11. 23Who were you in high school, if you had to describe him in one sentence?
12. 24What's a moment from your childhood you'd love to relive for one day?

Funny and random questions

For when the conversation needs a reset. These work best when you both answer, and the sillier the answer, the better.

1. 25If you had to be a contestant on one reality show, which one would you survive longest on?
2. 26What's the dumbest way you've ever hurt yourself?
3. 27If our relationship had a theme song, what would you pick, and what would I pick?
4. 28Which animal do you think could take you in a fight, honestly?
5. 29What's a hill you would die on that doesn't matter at all?
6. 30If you were a ghost, who would you haunt and how?
7. 31What would your wrestling entrance song be?
8. 32What's the worst haircut you've ever had, and who let it happen?
9. 33If you could only eat one cuisine for the rest of your life, which one, and why is it the wrong answer?
10. 34What's a conspiracy theory you half believe?
11. 35If you were famous, what would you be famous for, realistically?
12. 36What's the most useless fact you know by heart?

Deep questions to ask your boyfriend

Save these for when you have time and privacy. Go first with your own answer if he seems unsure, and don't push for more than he wants to share.

1. 37What's something you believed at 20 that you don't believe anymore?
2. 38When do you feel most like yourself?
3. 39What's a decision you made that changed the direction of your life?
4. 40Is there something you're still proud of that nobody really noticed?
5. 41What does a good day look like for you when nothing special happens?
6. 42What are you most afraid people will find out about you?
7. 43Who do you go to when you need to hear the truth?
8. 44What do you think you got from your dad, and what did you decide not to take?
9. 45What's something you wish you'd been told when you were younger?
10. 46When was the last time you cried, and do you remember why?
11. 47What do you think you'll regret not doing if you don't start soon?
12. 48How do you want people to describe you when you're not in the room?

Questions about your relationship

Questions about the two of you. These tend to bring up good memories and, now and then, something you'd both been meaning to say.

1. 49What did you think of me the first time we met, honestly?
2. 50When did you realize this was turning into something serious?
3. 51What's a moment with me you replay in your head?
4. 52What's something I do that you've never told me you love?
5. 53What's one thing I do that drives you a little crazy?
6. 54When do you feel most appreciated by me?
7. 55What's the best date we've been on, and what made it work?
8. 56Is there something you've wanted to try together but haven't brought up?
9. 57How do you prefer to make up after we argue?
10. 58What's something you've learned about relationships from being with me?
11. 59Do you feel like you can tell me when something's wrong?
12. 60What's one small thing I could do this week that would make your week better?

Questions about the future

Plans, priorities, and what he pictures down the road. Some of these are big; ask them as curiosity, not as a test he can fail.

1. 61Where would you live if your job and family didn't matter at all?
2. 62What does 'settled' look like to you, and how far away does it feel?
3. 63Do you want kids, and has your answer changed over the years?
4. 64What would you do with a year off and enough money to cover it?
5. 65Which of your friends' relationships do you look at and think 'I want that'?
6. 66What do you want to be doing for work in ten years, if you could pick freely?
7. 67How do you picture a regular weeknight when you're 40?
8. 68What's a trip you want to take before you're too old to enjoy it?
9. 69Would you rather have a big house far out or a small place in the middle of everything?
10. 70How involved do you want your family to be in our life?
11. 71What's something you want to learn properly at some point?
12. 72What's one thing you want us to have done together a year from now?

The questions most couples put off

Money, conflict, and expectations. Not first-date material, but couples who have these talks early tend to have fewer surprises later.

1. 73Are you a saver or a spender, and which one were your parents?
2. 74What's a purchase you'd consider too big to make without talking to me first?
3. 75How do you feel about splitting costs: 50/50, by income, or something else?
4. 76When you're upset, do you want to talk right away or have space first?
5. 77What's something from a past relationship you don't want to repeat?
6. 78How do you feel about holidays: whose family, how often, how long?
7. 79What's your honest take on where we should live in the next few years?
8. 80What's a dealbreaker for you that you've never said out loud?
9. 81How do you want to handle it when one of us is having a hard time with work?
10. 82How much alone time do you need in a normal week?
11. 83What does cheating mean to you? Where's the line?
12. 84If one of us got a great job in another city, how would you want to decide?

Flirty questions to ask your boyfriend

Playful questions for text or for a night in. They keep things light while still telling you something.

1. 85What's the first thing you noticed about me?
2. 86What outfit of mine do you secretly have a favorite of?
3. 87When did you first want to kiss me?
4. 88What's something I do that I probably don't realize is attractive?
5. 89What's your favorite way to spend a lazy morning with me?
6. 90If you planned the perfect night for us, what would happen from start to finish?
7. 91What's a compliment you've thought about me but never said?
8. 92What's the most romantic thing anyone has ever done for you?
9. 93Which of my habits did you find cute at first and still do?
10. 94Where would you take me if we could leave tonight?

Questions to text your boyfriend

Short enough to send between meetings, and specific enough to get more than 'lol'. Good for long distance or the middle of a slow day.

1. 95What's the best thing that's happened to you today, even if it's tiny?
2. 96Rate your day out of 10 and tell me what would've made it a 10.
3. 97What are you craving right now?
4. 98What song is stuck in your head?
5. 99Quick: what are you most looking forward to this week?
6. 100If I showed up right now, what would we do?
7. 101What's something that made you think of me today?
8. 102Be honest: what are you procrastinating on?
9. 103Send me the last photo in your camera roll, no explanation.
10. 104What's one thing you want to do together next time we see each other?

Questions to see how well he knows you

Turn it around. These are about you, and they make the best quiz questions because there's a clear right answer and he either knows it or he doesn't.

1. 105What's my coffee or drink order, exactly as I'd say it?
2. 106What would I pick for a last meal?
3. 107Which of my friends have I known the longest?
4. 108What's the one chore I'll always volunteer for?
5. 109What do I do first when I get home after a bad day?
6. 110What's my most-used emoji?
7. 111Which movie can I quote from start to finish?
8. 112What's my biggest pet peeve when we're out in public?
9. 113What was I wearing on our first date?
10. 114If I had a free afternoon, would I go out or stay in?
11. 115What's the gift I've hinted at for months?
12. 116What would I name a dog?