What are good questions to ask your boyfriend?

Open-ended questions work best, like “What’s a memory you think about more than you’d admit?” or “What did you want to be when you were ten?” They invite stories instead of one-word answers and often lead to follow-up questions.

What are some deep questions to ask your boyfriend?

Ask about values, fears and turning points: what he is most proud of, what he would change about his childhood, or what makes him feel truly appreciated. Save them for a calm moment when neither of you is rushed.

How do I ask my boyfriend questions without it feeling like an interview?

Answer the question yourself too, follow up on what he says instead of moving straight to the next question, and mix deep questions with funny ones. Turning it into a game, like taking turns drawing questions, also keeps it light.

80 Questions to Ask Your Boyfriend: Deep, Funny & Flirty

How to use these questions

A list of questions only works if it feels like a conversation, not a quiz. Three things help:

Answer them too. Ask, listen, then share your own answer. It’s a swap, not an interview.
Follow the interesting answer. If one question sparks a story, stay there. You don’t have to get through the list.
Match the mood. Funny and random questions are great for a road trip or texting. Deep questions land better on a quiet evening.

Questions to get to know him better

Good for a newer relationship, or for learning something you never thought to ask.

What did you want to be when you were ten?
What’s a hobby you’ve always wanted to try but haven’t?
Who was your best friend growing up, and are you still in touch?
What’s the best trip you’ve ever taken?
What’s your favorite way to spend a lazy Sunday?
What’s a food you’ll never get tired of?
Which family member are you most like?
What’s a song that instantly takes you back to a specific time?
What’s the best piece of advice anyone ever gave you?
What were you like in high school?
If you could live anywhere for a year, where would it be?
What’s something you’re weirdly good at?
What’s a movie you could watch over and over?
What does your perfect day look like from start to finish?
What’s something most people don’t know about you?

Deep questions to ask your boyfriend

What’s a moment in your life that changed the way you see things?
What are you most proud of that you rarely talk about?
What’s something you’re still trying to figure out about yourself?
When do you feel most like yourself?
What’s a fear you’ve never really said out loud?
What did your parents get right, and what would you do differently?
What makes you feel truly appreciated?
Is there anything you wish you’d done differently in the last few years?
What does a good life look like to you?
Who has had the biggest influence on who you are today?
What’s the hardest thing you’ve ever had to let go of?
How do you like to be comforted when you’ve had a bad day?
What’s something you believed strongly five years ago that you’ve changed your mind about?
What’s a memory you think about more than you’d admit?
What do you hope people say about you when you’re not in the room?

Funny questions to ask your boyfriend

What’s the most embarrassing thing that’s happened to you in public?
If you were a kitchen appliance, which one would you be?
What’s the weirdest thing you believed as a kid?
Which celebrity do you think would be the worst roommate?
What would your wrestling entrance song be?
If our pet (or future pet) could talk, what would it complain about first?
What’s the dumbest way you’ve ever hurt yourself?
If you had to eat one fast-food meal for the rest of your life, which would it be?
What’s a completely useless talent you have?
What’s the worst haircut you’ve ever had?
What’s a hill you’d die on that doesn’t matter at all?
If you were a villain, what would your evil plan be?
What’s the weirdest thing you’ve ever searched online?
What would you name a boat if you owned one?
What do you think I’d be famous for if I became famous?

Flirty questions to ask your boyfriend

Playful, a little bold, nothing explicit. Perfect for texting or a cozy night in.

What was the first thing you noticed about me?
When did you realize you liked me?
What’s your favorite outfit I wear?
What’s a date you’ve secretly wanted us to go on?
What’s something I do that you find really attractive?
Do you remember what you thought after our first date?
What’s your favorite memory of us so far?
If you could plan our perfect night, what would we do?
What’s a compliment you’ve wanted to give me but haven’t?
Where’s the most romantic place you’d want to kiss me?
What’s one thing I do that always makes you smile?
What song makes you think of me?

Random questions to ask your boyfriend

Great for long drives, waiting in line or when the conversation goes quiet.

Would you rather explore space or the deep ocean?
What’s the best meal you’ve ever had?
If you could master any skill overnight, what would you pick?
What’s a smell that brings back a strong memory?
What’s the most useless thing you own that you’ll never throw away?
If you won the lottery tomorrow, what’s the first thing you’d buy?
What would your last meal be?
Which decade would you live in if you could?
What’s the best concert or live show you’ve been to?
What’s an animal you think is underrated?
Cats or dogs, and why are you wrong?
If you started a business, what would it be?
What’s the strangest dream you remember?

Questions about your relationship and future

What’s something you think we do really well as a couple?
Is there anything you’d like us to do more often?
What does your ideal home look like in ten years?
What’s a tradition you’d like us to start?
Where’s somewhere you want us to travel together?
How do you like to make up after an argument?
What’s one goal you want us to work on together?
What’s a small thing I could do that would make your week better?
What does a good weekend together look like to you?
What’s something about us you hope never changes?

That’s 80 questions in total: 15 to get to know him, 15 deep, 15 funny, 12 flirty, 13 random and 10 about your future.

Questions to ask your boyfriend before moving in together

What does a clean home mean to you?
How should we split the bills and the chores?
How much alone time do you need during the week?
How do you feel about guests staying over?
What is one habit of yours I should know about before we share a space?
What would make our home feel like ours?

Questions to ask your boyfriend over text when you’re bored

What are you doing right now, and are you enjoying it?
What is a song you have had on repeat this week?
What is the best thing you ate today?
If we could teleport anywhere tonight, where would you pick?
What is something small that made you smile today?
Send me the last photo in your camera roll. What’s the story?
Which three apps do you use the most?

Turn the questions into a game

If asking question after question feels too much like an interview, make it a game. Take turns drawing a number between 1 and 15 and answer that question from the section you choose. Or play the 21 questions game, where each of you gets 21 questions and a pass.

You can also let a phone do the asking. Duoo is an iPhone and iPad app with 15 games for two to eight players, including Would You Rather, Never Have I Ever and Who’s Most Likely To. It works offline and uses one phone passed between you, so it’s easy to pull out on a date night. Duoo is free to download, and a subscription with a free trial unlocks every game and category.

For more prompts, try our would you rather questions for couples, Never Have I Ever questions for couples or the truth or dare questions for couples. And if you want something more playful than talking, here are some games to play on a date.

Asking someone else? See our questions to ask your girlfriend, questions to ask your partner, questions to ask a guy and questions to ask friends.