Questions to Ask Your Boyfriend
87 questions · By Dima Tretyak, creator of DeepTalk · Updated
Ask your boyfriend how his day was and you'll probably hear "fine." Ask something specific and you get a story. The questions below are the specific kind: easy to answer, hard to brush off with one word, and clearly asked because you want to know.
They're grouped by mood, so you can grab a few getting-to-know-you questions for a new relationship, a flirty round for a text, or the bigger where-are-we-going questions for a quiet evening. Some come from the question decks in the DeepTalk app, and the rest were written for this page.
Questions to get to know him better
Good for the first few months, or any time you realize there's a whole chapter of his life you've never asked about. Still early days? See our first date questions.
- 1What did you want to be when you were ten, and how far off did you end up?
- 2Who in your family are you most like, and how do you feel about that?
- 3What's a subject you could talk about for an hour without getting bored?
- 4What were you like in high school, honestly?
- 5Which friend has known you the longest, and what would they tell me about you?
- 6What's a small thing that can turn a bad day around for you?
- 7What's something you're weirdly competitive about?
- 8What does a perfect lazy Sunday look like for you?
- 9What's a skill you picked up that surprises people?
- 10What's the best advice anyone who raised you ever gave you?
Deep questions to ask your boyfriend
Save these for when you're both relaxed and off your phones. Ask one, then mostly listen.
- 11What's a belief you held strongly at twenty that you've since let go of?
- 12Where are you, and who are you with, when you feel most at ease?
- 13What's something from your childhood you're still carrying and would like to put down?
- 14What does being a good man mean to you, and where did you learn it?
- 15What's a fear you rarely admit, even to yourself?
- 16Who do you go to when things fall apart, and why them?
- 17What's a moment you were proud of yourself that nobody else noticed?
- 18What do you wish people asked you about more often?
- 19What's the hardest thing you've ever had to forgive?
- 20How do you want the people closest to you to remember you?
- 21What's your biggest fear around being vulnerable?
Rather play than scroll? DeepTalk deals these out one card at a time.
Romantic and flirty questions
Most of these work just as well over text as they do on a date. For more, see our love and romance questions.
- 22What did you notice about me first, and what did you only notice later?
- 23When did you realize this was more than just dating?
- 24What's a favorite memory of us that you've never actually told me about?
- 25What's something I do that I probably don't realize is attractive?
- 26What would our perfect date look like if money and time didn't matter?
- 27If you had to send me one text that would make my whole day, what would it say?
- 28What's the most romantic thing someone's ever done for you?
- 29What's a small act of love that means a lot to you?
- 30What's one gesture that instantly melts your heart?
- 31When do you feel most connected to me?
Questions to ask your boyfriend over text
Short enough to answer between meetings, interesting enough to keep the chat going.
- 32What's something that made you smile today that you didn't tell anyone about?
- 33What song have you had on repeat this week?
- 34What's the last thing you googled that you'd be embarrassed to explain?
- 35If you could teleport here right now, what's the first thing we'd do?
- 36What's one thing you're looking forward to this week?
- 37What's the story behind the last photo in your camera roll?
- 38What are you craving right now, food or otherwise?
- 39What's a memory of us that popped into your head recently?
- 40What's one word for how your day went, and what's the story behind it?
- 41What would you be doing right now if you had the day off?
Funny and random questions
For road trips, long lines, and nights when neither of you has the energy for anything serious.
- 42What's the most useless fact you know by heart?
- 43If our relationship had a theme song, what would it be?
- 44What's a hill you're willing to die on that nobody else cares about?
- 45What's the strangest thing you believed as a kid?
- 46If you could swap lives with one of your friends for a week, who would it be?
- 47What's a food combo you love that most people find disgusting?
- 48What would your walk-up song be if you were a pro baseball player?
- 49What's the most embarrassing thing you've done to impress someone?
- 50Which fictional character do you secretly relate to the most?
- 51If I ran your social media for a week, what would you be scared I'd post?
Would you rather questions for your boyfriend
Quick picks that start a debate. Want a longer list? Try our would you rather questions.
- 52Would you rather go on a road trip with no plan or a vacation where every hour is scheduled?
- 53Would you rather I cook you dinner or plan a surprise night out?
- 54Would you rather have a lazy morning in bed or an early hike to watch the sunrise?
- 55Would you rather always know when I'm upset or always know how to cheer me up?
- 56Would you rather live in a tiny apartment in the city or a big house in the middle of nowhere?
- 57Would you rather give up your phone for a week or coffee for a month?
- 58Would you rather have a big wedding with everyone or a tiny one with five people?
- 59Would you rather see your favorite band live or your favorite team win a final in person?
Questions about your relationship
A gentle check-in on how you're doing as a couple. Ask with curiosity, not as a test. More in our questions for couples.
- 60What's one thing I do that makes you feel really appreciated?
- 61What's something you need from me that you rarely ask for?
- 62How do you prefer to make up after an argument?
- 63What's something we used to do that you miss?
- 64What does feeling respected by me look like day to day?
- 65What's a behavior that breaks your trust quickly?
- 66How do you like to be comforted when you're upset?
- 67What's something you'd like us to do more often?
- 68What part of our relationship do you think we're getting really right?
- 69What's a habit of mine you've gotten used to but still secretly find annoying?
Questions to ask when it's getting serious
The practical side of a long-term relationship. Better to talk it through early than to find out later.
- 70What does commitment mean to you in everyday terms?
- 71How do you feel about living together, and what would make it work for you?
- 72How did your parents handle conflict, and what did you learn from it?
- 73What role do you want your friends and family to play in our life together?
- 74How do you picture splitting chores, money and plans when we share a home?
- 75How do you feel about marriage, and has that changed over time?
- 76How do you feel about having kids someday?
- 77What's a dealbreaker for you in a long-term relationship?
- 78What would you need from me if one of us got a job in another city?
- 79How do you want us to handle big decisions we disagree on?
Questions about the future
For when things are getting serious and you want to know if you're heading the same way.
- 80Where do you see us in five years?
- 81What kind of traditions do you want us to build?
- 82What's one thing you want to do differently than your parents?
- 83What's something you want us to learn or try together this year?
- 84What does a good life look like to you at forty?
- 85How do you feel about the way we handle money right now?
- 86Which city could you see us living in if we moved somewhere new?
- 87What would make you feel ready for a bigger commitment?
How to use these questions
- Pick three, not thirty. A few questions with real follow-ups beat a rapid-fire quiz.
- Let follow-ups do the work. "What made you think that?" and "What happened next?" turn a short answer into a conversation.
- Match the moment. The funny and flirty sections are great over text or on a drive. Save the deep and future ones for a quiet evening together.
- Answer them yourself too. It's a conversation, not an interview.
- If he gives a one-word answer, don't push. Share your own answer first and come back to it another time.
Play them as cards instead
DeepTalk deals questions like these one card at a time, with 20 decks and over 2,000 questions for couples and friends.
Frequently asked questions
What are good questions to ask your boyfriend?
Good questions are specific and open-ended, so he can't answer with a single word. "What's a small thing that can turn a bad day around for you?" works better than "Are you happy?" Mix a few light ones with one or two deeper questions, and ask follow-ups instead of moving straight to the next question.
What are some deep questions to ask your boyfriend?
Try questions about how he has changed and what shaped him, like "What's a belief you held strongly at twenty that you've since let go of?" or "Who do you go to when things fall apart, and why them?" Deep questions land best in person, when neither of you is in a hurry.
How do I get my boyfriend to open up?
Start light, go first, and don't treat his answers as a test. Sharing your own answer makes it easier for him to share his. Side-by-side settings like a walk or a drive often feel less intense than a face-to-face talk.
Can I ask these questions over text?
Yes. There's a whole section of questions to ask your boyfriend over text, and the funny and flirty ones work well there too. Questions about trust, your relationship or the future are usually better in person, where tone and body language don't get lost.