100 Questions to Ask Your Boyfriend
These questions are for any couple, new or long term, who want to talk about more than what to eat tonight. Pick a group, ask one or two at a time, and let the answers turn into a real conversation. The last group works as a couple quiz to see how well he knows you.
Getting to know him better
- You get a free day with no plans and no phone. How do you spend it?
- When you are stressed, what do you need most from me?Example: space / a hug / advice / just listening
- What is something you were really into as a kid that you still secretly love?
- Who in your family are you most like, and does that make you happy or nervous?
- What is a small thing that can ruin your whole mood?
- You get a surprise bonus at work. What do you do with it?Example: save it / trip / gadget / treat us
- What did you want to be when you grew up, and how far off is it from today?
- Which friend knows you best, and what would they say about me?
- What is a skill you wish you had learned earlier?
- When do you feel most like yourself?
- How do you recharge after a long week?Example: sleep in / friends / gaming / alone time
- What is something people often get wrong about you on first meeting?
- What is the best advice anyone ever gave you?
- What is your favorite memory from school or college?
Fun and silly questions
- We swap lives for a day. What is the first thing you do as me?
- A zombie outbreak starts tonight. What is your role in our team?Example: leader / cook / runs first / makes jokes
- You can only eat one dish for a whole year. What do you pick?
- If our relationship had a theme song, what would it be?
- Which cartoon character are you most like, honestly?
- You win a free trip tomorrow, but you have one hour to pack. Where do we go?Example: beach / mountains / big city / anywhere
- What is the most embarrassing thing you have done in front of a crush?
- If you were a dessert, which one would you be and why?
- You can have one superpower, but only for small daily things. Which one?
- What is the weirdest food combo you secretly enjoy?
- If we had a pet together, what would it be?Example: dog / cat / fish / a very loud parrot
- Which song do you sing loudest when no one is around?
- What would your job be in a movie about us?
- What is your most useless talent?
Deep questions to ask your boyfriend
- You have a bad day and I ask what is wrong. Do you want to talk or be distracted?
- What is something you have never told anyone but would tell me?
- What makes you feel truly loved, more than words?
- When was the last time you cried, and what caused it?
- What scares you most about the future?Example: money / health / being alone / not being enough
- Is there a moment from your past you would change if you could?
- What does a good life look like to you at 60?
- How has your idea of love changed since your first relationship?
- What is one thing you are still proud of years later?
- What do you find hardest to forgive?
- When you feel low, how can I tell?Example: quiet / short replies / extra jokes / stay busy
- What is a belief you had growing up that you let go of?
- Who has shaped who you are more than anyone else?
- What do you need to hear more often from me?
Want to see if he really knows you? Turn these into a quiz.
About us
- We have a fight at night. Do you want to talk it out or sleep on it?
- What did you first notice about me, and what did you think?
- When did you know you wanted to be with me?
- I am upset but say "I am fine." What do you do?Example: ask again / give space / bring snacks / hug
- What is your favorite memory of us so far?
- What is one thing I do that makes you smile without me knowing?
- Is there something I do that bugs you a little but you never said?
- How do you most like to show love?Example: words / gifts / time / helping out / touch
- What is one thing we should do more often together?
- How do you feel when I spend a weekend with my friends without you?
- What do you think we are best at as a couple?
- What is a small habit of mine you would miss if I was away?
- If you could relive one date with me, which one?
- What is one thing you want us to work on together?
Future and big plans
- We get a job offer in a new city. Do we move or stay?
- Where do you see us living in five years?Example: same city / new city / abroad / a small town
- What is one trip you want us to take before we turn old?
- How do you feel about money: saver, spender or somewhere in between?
- Do you want kids someday, and how many?
- What does a perfect weekend look like when we are older?Example: quiet home / travel / family / friends
- How involved do you want our families to be in our life?
- What is one big goal you want to reach in the next three years?
- How would you want to split chores if we lived together?
- What is one tradition you want us to start?
- If money were no issue, what would you do for work?
- What would make you feel ready for a bigger step with me?
- One of us gets a dream job far away. How do we handle it?Example: long distance / move together / turn it down
- What is one thing you hope never changes about us?
Habits and little things
- Your alarm rings on a Sunday. What happens next?Example: snooze three times / up right away / back to sleep
- It is 11 pm and you are hungry. What do you eat?
- You get a text you do not want to answer. Do you reply late, never, or right away?
- You find a spider in the room. What do you do?Example: catch it / call me / leave the room / ignore it
- How messy is your room on a normal day, from 1 to 10?
- What is the first thing you check on your phone in the morning?
- You are running late. What do you do?Example: text / call / just show up fast / blame traffic
- How do you like your tea or coffee?Example: strong / sweet / milky / neither
- What is one thing you always forget, no matter what?
- How long do you take to get ready to go out?
- What do you do when you cannot sleep?
- Which chore do you hate most and why?
- What is your go-to comfort show or movie?
- What do you always order at a new restaurant?
Questions for a couple quiz
- I have a free evening alone. What am I most likely doing?Example: reading / series / calling a friend / sleeping
- What is my biggest pet peeve?
- What is my go-to order when we get food?Example: pizza / biryani / noodles / burger
- Which of my friends do I talk to the most?
- What do I do first when I come home after a long day?
- What am I most scared of?Example: heights / spiders / the dark / being late
- Which song do I play on repeat right now?
- What is my dream place to travel to?
- I get a surprise gift. What makes me happiest?Example: flowers / chocolate / handwritten note / a book
- What is the one thing I always carry in my bag?
- Am I a morning person or a night owl?Example: early bird / night owl / neither / depends on coffee
- What is my comfort food on a bad day?
- When I am angry, what do I usually do?Example: go quiet / talk fast / walk away / cry
- What is a show I can watch again and again?
- Who do I call first with big news?
- What is my favorite way to spend a rainy day?
Questions in our quiz
Our quiz has its own set of questions with ready answers to pick from. See the quiz questions.
More lists: Questions to ask your girlfriend, This or that questions, Questions to ask your crush.
Common Questions
How many questions should I ask my boyfriend at once?
Three to five is plenty for one talk. Deep questions need time, so pair one deep question with a few fun ones. You can come back to the list on another day.
Which questions are best to start with?
Start with the fun and silly group or the habits group, since they are easy to answer and get you both laughing. Save the deep and future questions for a calm moment when you both have time.
Can I ask these questions over text?
Yes. Fun, habit and couple quiz questions work well over text and are good for long distance. For deep questions, a voice or video call often feels better because tone matters.
What if he does not want to answer a question?
Let it go and move to the next one. Some questions need trust or the right moment, and it is fine to come back later. The goal is to feel closer, not to test him.
How do I turn these into a couple quiz?
Make a free quiz on this site with no account. You answer 20 questions about yourself, share the link with him, and he guesses your answers. His score, and anyone else who plays, shows on your leaderboard.
Make your couple quiz and send him the link.