Questions · For your boyfriend
100 questions to ask your boyfriend
Three months in or ten years in, there’s always more to find out. These 100 questions to ask your boyfriend start fun and random, then go deeper: who he is, where you’re both headed, the two of you, and a few flirty ones for later. Every one is written to get more than a one-word answer.
By The Couples Company100 questions8 min read
How to use this list
Make it two-way: you ask the pink numbers, he asks you the teal ones.
- Start with the fun ones. Save the deep questions for a slow evening, not a quick text.
- Follow up before you move on. “What happened next?” turns an answer into a story.
- There are no wrong answers, and either of you can pass.
Fun and random
Questions 1 to 25
Easy openers for a long drive or a lazy Sunday, and nobody can get them wrong.
- 1
What’s a food you only pretend to like?
- 2
What could you teach a class on tomorrow with zero preparation?
- 3
What’s your most useless talent? Demonstrations are encouraged.
- 4
Which fictional world would you move to, and what job would you have there?
- 5
What’s the most ridiculous way you’ve ever gotten hurt?
- 6
What’s a tiny, unimportant opinion you would defend to the end?
- 7
What did you believe as a kid that turned out to be completely wrong?
- 8
If you could only eat at one chain restaurant for the rest of your life, which one wins?
- 9
What would your pro wrestling name be, and what’s your entrance song?
- 10
What’s the worst haircut you’ve ever had? Is there photo evidence?
If there’s a photo, you need to see it. This part is not optional.
- 11
Which animal do you think would be the rudest if it could talk?
- 12
What movie could you act out a scene from right now, word for word?
- 13
If you could be instantly great at one hobby without practicing, which would you pick?
- 14
What’s the best thing you’ve ever found in an old coat pocket?
- 15
What song do you secretly know every word to?
- 16
If you could ban one mildly annoying thing forever, what goes first?
- 17
What’s a job you think you’d be surprisingly good at?
- 18
You get a highway billboard for a month. What does it say?
- 19
What smell takes you straight back to being a kid?
- 20
What’s the weirdest thing you’ve ever bought online?
- 21
Which reality show do you think you could actually win?
- 22
What’s the weirdest dream you still remember?
- 23
If you owned a boat, what would you name it?
- 24
If we swapped jobs for a week, how long would you last in mine?
- 25
Would you still love me if I started clapping when the plane lands?
A proud member of the would-you-still-love-me family. There are plenty more where it came from.
Play would you rather next
Deep questions
Questions 26 to 50
For a slow evening: who he was, who he is and what he doesn’t often say out loud.
- 26
What’s something you did as a kid that you’re still proud of?
- 27
Who shaped your idea of the kind of man you wanted to be?
It might be a dad, a coach or an older brother, or someone he decided he’d never be like. Both answers tell you a lot.
- 28
Where are you when you feel most at ease: a place, a person, a hobby?
- 29
What moment changed the direction of your life, even if nobody else noticed?
- 30
What do you wish people asked you about more often?
- 31
Who have you forgiven, and how did you get there?
- 32
How did your family show love when you were growing up?
- 33
What’s a fear that has quietly shaped your choices?
- 34
What are you still trying to prove, and who are you proving it to?
- 35
What does a really good day look like for you, start to finish?
- 36
What’s the best advice you ever ignored?
- 37
When was the last time something moved you to tears?
If he’d rather not say, let it go. Asking already tells him it’s safe to answer one day.
- 38
Which friendship from your past do you miss the most?
- 39
What part of yourself are you working on right now?
- 40
What do people get wrong about you when they first meet you?
- 41
Is there a decision you still aren’t sure was the right one?
- 42
What’s something you need but find hard to ask for?
- 43
Who do you call when things go wrong, and why them?
- 44
What does success mean to you now, and has that changed?
- 45
What’s a belief you grew up with that you’ve since let go of?
- 46
What makes you feel respected?
- 47
When you’re stressed, what do you actually need from the people around you?
- 48
What’s the hardest thing you’ve ever done?
- 49
If you could ask your younger self one question, what would it be?
- 50
What do you hope people say about you when you’re not in the room?
The future
Questions 51 to 70
Big plans, small hopes and where he pictures the two of you landing.
- 51
Where would you live if work and family weren’t part of the equation?
- 52
What’s on your list of things to do before you get old?
- 53
What would you do with a fully paid year off?
- 54
If you could switch careers tomorrow with zero risk, would you? To what?
- 55
Do you see yourself as a parent someday? If so, what kind?
Yes, no and maybe are all fair answers for now. If it’s a big open question for you two, give it its own evening.
More questions on kids and family - 56
What kind of home do you picture us in: a city apartment, a house with a yard, something unusual?
- 57
What’s a skill you want to learn in the next few years?
- 58
What’s something you’re looking forward to that you haven’t told anyone about?
- 59
Which holiday traditions from your family do you want to keep, and which would you happily drop?
- 60
What would you need in place to feel truly settled?
- 61
Where in the world should we travel together first?
- 62
What are you saving up for, or wish you were?
- 63
Do you want to live near your family, far from them, or somewhere in between?
- 64
How do you want to celebrate your next big birthday?
- 65
What do you want to be really good at by the time you’re 70?
- 66
What kind of old man are you planning to be: the gardener, the traveler, or the one who argues with the TV?
- 67
Is there a big risk you want to take in the next five years?
- 68
What’s one thing you’d like us to be doing differently a year from now?
- 69
How do you feel about marriage, in general and for us?
No pressure on the answer. This one is about understanding each other’s view, not setting a date.
- 70
Who do you hope is still in our lives thirty years from now?
About us
Questions 71 to 90
The romantic ones: how it started, what he notices and what keeps getting better.
- 71
What was your honest first impression of me?
- 72
When did you know you wanted to keep seeing me?
- 73
What’s your favorite memory of us so far?
- 74
What do I do that always makes you laugh?
- 75
Which of my habits seemed strange at first but grew on you?
- 76
What’s the best way for me to show you I love you: words, time, help, gifts or touch?
Take the free love language quiz - 77
What do you think we do better than most couples?
- 78
What small thing could I do more often that would make your week?
- 79
Which song makes you think of me?
- 80
Which date of ours would you repeat exactly as it was?
- 81
What did you tell your friends about me after our first date?
- 82
What’s something you’ve learned from me?
- 83
How have we changed since we met?
- 84
What’s something about me you’d brag about to a stranger?
- 85
What’s a habit of ours you hope we still have in twenty years?
- 86
When I go quiet, what do you assume is going on, and how often are you right?
- 87
Where do you think we’re most alike, and where are we most different?
Try the couples compatibility test - 88
On a scale of one to ten, how well do you think you know me?
Test it with our free quiz - 89
When were you proudest to be with me?
- 90
What’s a small way I’ve changed your daily routine since we met?
A few flirty ones
Questions 91 to 100
Light, a little cheeky and best asked with a smile.
- 91
What was the first thing about me you found attractive?
- 92
Which outfit of mine do you secretly love the most?
- 93
Where would you most like to kiss me that we haven’t yet?
- 94
What do I do that you find irresistible, without me realizing it?
- 95
If you planned our perfect date night, what would happen?
- 96
What’s the best compliment I’ve ever given you?
- 97
Do you remember what I was wearing when we first met?
- 98
When do you think I look my best?
- 99
What’s a romantic thing you’ve always wanted to do but never told me?
- 100
What’s the flirtiest text I’ve ever sent you, and what did you think when you read it?
Play it as a game
Think you know him? Prove it.
WhoIs? is our card game for couples. One of you reads a card, the other says who it describes, and if you agree, the card is theirs. Make a bet before you start: most cards wins it.
167 question cards · 12 answer cards · 2 to 12+ players
From the deck
- Who is:Funnier?
- Who is:The one who controls the TV?
- Who was:The first one to say “I love you”?
