Questions to ask your boyfriend
From the deep ones to the flirty ones, here is what to actually ask him.
Some nights you want to know him a little better and the usual how-was-your-day runs out fast. These are the questions that go somewhere.
They are grouped so you can pick your mood: deep ones for a slow evening, fun ones for a drive, flirty ones for late at night, and a set that works over text. Ask one, then actually listen to the answer.
Boyfriend / Deep questions
What is something you are proud of that you never brag about?
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Deep questions
- 1What is something you wish I understood about you?
- 2When do you feel most respected by me?
- 3What is a fear you have never said out loud to me?
- 4What does being a good man mean to you?
- 5Who do you become when you are most stressed?
- 6What do you think you are like to love?
- 7What is something you are proud of that you never brag about?
- 8What did you learn about relationships from your parents?
- 9When was the last time you felt truly seen?
- 10What is a dream you have quietly given up on?
- 11What makes you feel safe with someone?
- 12What is the hardest thing you are dealing with right now?
- 13What is a compliment you wish you got more often?
- 14What are you still trying to prove, and to whom?
- 15What would you do differently if no one would judge you?
- 16What always makes you feel like a kid again?
- 17What part of your day do you most look forward to?
- 18What do you wish more people asked you about?
Fun questions
- 19What is the most fun you have ever had in one day?
- 20What would your perfect weekend with me look like?
- 21What is a hobby you would pick up if you had the time?
- 22What is the best purchase you have ever made?
- 23If you could be famous for one thing, what would it be?
- 24What is your go-to karaoke song, no shame?
- 25What is the weirdest food combination you secretly love?
- 26What would you do first if you woke up as me?
- 27What is a small win that made you way too happy?
- 28What movie could you rewatch a hundred times?
- 29What is your most irrational fear?
- 30If we had a free plane ticket right now, where are we going?
- 31What is a talent you wish you had?
- 32What is your favorite way to waste a Sunday?
- 33What is the dumbest thing you have ever cried at?
- 34What trend did you fully fall for at the time?
Questions about your relationship
- 35What was going through your head on our first date?
- 36When did you realize you wanted to be with me?
- 37What do you brag about me to your friends?
- 38What is a moment with me you keep coming back to?
- 39What do you think we should be better at?
- 40When do you feel most like a team with me?
- 41What is something I do that instantly relaxes you?
- 42What are you most grateful for about us?
- 43What do you hope people see when they look at us?
- 44What scared you most about falling for me?
- 45What do you never want us to lose?
- 46When have you felt proudest to be with me?
- 47What do you wish I did more often?
- 48What does home feel like to you now?
- 49What is one promise you want to make to me?
- 50What is a tradition you want us to start?
Questions about his past
- 51What were you like before we met?
- 52What was the hardest year of your life?
- 53Who believed in you when you needed it most?
- 54What is a lesson you learned the hard way?
- 55What did your first heartbreak teach you?
- 56What is a memory of your childhood home you love?
- 57Who did you look up to growing up?
- 58What is something from your past you have made peace with?
- 59What is the bravest thing you did before me?
- 60What friendship shaped who you are?
- 61What is a mistake you are actually grateful for?
- 62What did you believe about love before us?
- 63What is a place from your past you want to show me?
- 64What were your parents like when you were young?
- 65What version of you do you miss sometimes?
- 66What did you want to be when you grew up?
Questions about the future
- 67Where do you want us to be in five years?
- 68What kind of father do you think you would be?
- 69What does your ideal life look like at sixty?
- 70What is a goal you have not told anyone about?
- 71What do you want our home to feel like one day?
- 72What adventure do you want us to have next?
- 73What are you working toward right now?
- 74What would make you feel like your life is a success?
- 75Where do you want to travel with me before we are old?
- 76What is one thing you want to build together?
- 77What do you want to be remembered for?
- 78What are you most hopeful about lately?
- 79What would you do if this year had no limits?
- 80What do you hope we are still doing at seventy?
Flirty questions
- 81What was the first thing you noticed about me?
- 82What do I do that you find impossible to resist?
- 83What is your favorite way to be kissed?
- 84When do you find me most attractive?
- 85What outfit of mine do you love the most?
- 86What is a memory of us that still gives you butterflies?
- 87What do you think about when you miss me?
- 88What is the most attractive thing about my personality?
- 89What did you want to do the first time you saw me?
- 90What is your idea of a perfect date night with me?
- 91What is your favorite thing about waking up next to me?
- 92What is your favorite kind of hug from me?
- 93What is something you have been wanting to tell me?
- 94Where is your favorite place for us to sneak away to?
Questions for a new boyfriend
- 95What made you want to ask me out?
- 96What are you looking for in a relationship?
- 97What should I know about how you show you care?
- 98What is a dealbreaker for you?
- 99How do you like to be supported on a bad day?
- 100What does dating me feel like so far?
- 101What is something you want me to know early?
- 102How do you handle disagreements?
- 103What makes you trust someone?
- 104What are you hoping this becomes?
Questions to ask over text
- 105What is the best part of your day so far?
- 106What are you thinking about right now?
- 107What is something small that made you smile today?
- 108What do you wish we were doing right now?
- 109What is on your mind that you have not said?
- 110What are you looking forward to this weekend?
- 111What song are you playing on repeat lately?
- 112What would you order if I brought you dinner tonight?
- 113What is a memory of us that popped up today?
- 114What do you need to hear right now?
- 115What is something you want to do with me soon?
- 116What made you think of me today?
