What are some deep questions to ask your boyfriend?

Ask about what shaped him and what he wants, for example: "What's something you've never told anyone?", "When did you feel most proud of yourself?" or "What do you need from me when you're stressed?"

How do I get my boyfriend to open up?

Ask specific questions instead of "How do you feel?", pick relaxed moments like a drive or a walk, listen without judging and don't push. Many men open up more when you're doing something together.

What are 21 questions to ask your boyfriend?

21 Questions is a game where you take turns asking each other questions. Mix light and personal ones, such as "What was your first impression of me?" or "What's your biggest fear?". The list below has 21 to start with.

150 Questions to Ask Your Boyfriend: Deep, Fun & Flirty

Asking your boyfriend questions is one of the best ways to get closer, whether you’ve just started dating or have been together for years. But if you’ve ever asked “What are you thinking about?” and got “Nothing”, you know that the question matters. Below are 150 questions, sorted by mood, plus a few tips from a guy’s point of view on how to ask them.

How to get him to open up

Most men don’t mind talking, they just don’t like being put on the spot. A few things make a big difference:

Talk side by side. Long drives, walks, cooking together or a late-night snack work better than sitting across from each other with a “We need to talk” face.
Be specific. “What was the best part of your week?” gets a real answer. “How are you feeling?” often gets “Fine”.
Start light, then go deeper. A fun question first makes the deep one easier.
Don’t punish honest answers. If he tells you something and you get upset, he’ll be more careful next time.
Answer too. Share your own answer. It turns questions into a conversation.
Pick your timing. Not in the middle of a game, right after work or when he’s hungry. Seriously.

Questions to get to know him

What was your favorite thing to do as a kid?
Who was your best friend growing up?
What were you like in high school?
What’s the best trip you’ve ever taken?
Which film can you watch again and again?
What’s a skill you’re proud of that most people don’t know about?
What did you want to be when you grew up?
Who taught you the most about being a man?
What’s your favorite way to spend a free Saturday?
What’s a hobby you’d love to try if you had more time?
What’s the best advice your dad or mom ever gave you?
Which friend would you call at 3 a.m.?
What’s the most spontaneous thing you’ve ever done?
What’s your comfort food after a bad day?
What’s something people often get wrong about you?

Deep questions to ask your boyfriend

Save these for quiet moments. Give him time to think before he answers.

When do you feel most like yourself?
What’s something you’ve never told anyone?
What are you most afraid of?
What’s the hardest thing you’ve ever been through?
When did you feel most proud of yourself?
What do you wish you had known five years ago?
What does success mean to you?
Is there something you regret not doing?
What do you need from me when you’re stressed?
What did your parents’ relationship teach you about love?
What’s something you’re still trying to forgive yourself for?
When was the last time you cried?
What part of yourself are you working on right now?
What’s a belief you changed your mind about?
Who has had the biggest influence on your life?
What makes you feel respected?
What’s a dream you’ve given up on?
What’s the best compliment you’ve ever received?
How do you know when you can trust someone?
If you could talk to your younger self for five minutes, what would you say?

Fun questions

If you could have any superpower for a day, what would you do?
What’s your most useless talent?
Which fictional character are you most like?
What’s the worst haircut you’ve ever had?
If you were a professional athlete, which sport would it be?
What would your last meal be?
What’s the most embarrassing song on your playlist?
If you won the lottery, what’s the first thing you’d buy?
What’s the weirdest food combination you secretly love?
Which celebrity would play you in a film about your life?
What’s the dumbest way you’ve ever hurt yourself?
If animals could talk, which one would be the most annoying?
What’s a trend you’ll never understand?
What would your entrance song be?
What’s the strangest dream you remember?
If you could master one instrument overnight, which one?
Which video game world would you want to live in?
What’s your go-to karaoke song?
What would you do with a whole day completely alone?
What’s the best prank you’ve ever pulled?

Flirty questions to ask your boyfriend

Playful questions that work best with a smile and the right mood.

What did you think the first time you saw me?
What’s your favorite thing about the way I look?
Which outfit of mine do you like best?
What was going through your head on our first date?
Do you remember our first kiss? What was it like for you?
What’s something I do that you find really attractive?
When do you think I look best?
What would your perfect night in with me look like?
What’s the cheesiest pickup line that would actually work on you?
Where’s your favorite place to be kissed?
What’s one thing you’d like me to surprise you with?
What do you think about when you miss me?
If we had a whole weekend with no plans, what would we do?
What’s the most attractive quality a woman can have?
What’s a compliment you’d love to hear more often?

Romantic questions

When did you first realize you liked me?
What’s your favorite memory of us?
Which day with me would you live again?
What’s something small I do that makes you feel loved?
What’s your idea of a perfect date?
Which song reminds you of us?
Do you believe in love at first sight?
What made you want to be in a relationship with me?
How do you like to be comforted?
What’s your love language?
What’s the most romantic thing you’ve ever done for someone?
Where would you like to travel with me?
What do you love most about our relationship?
What does “home” mean to you?
What’s something you’d like us to do together for the first time?

Questions about your relationship

These keep you close and help you spot small problems before they get big.

What do you think we do really well as a couple?
Is there something you’d like more of from me?
Is there something you’d like less of?
When do you feel closest to me?
How can I support you better when you’re stressed?
How much time with your friends do you need, and do you get enough?
How do you like to make up after an argument?
Is there something you’ve wanted to tell me but didn’t know how?
What’s one thing we should try as a couple this year?
What does a good weekend together look like for you?
How do you feel about my friends?
What makes you feel appreciated by me?
What’s a habit of ours you never want to lose?
Do you feel like you can be completely yourself around me?
How do you show love, and how do you like to receive it?
What’s a relationship you admire?
What does commitment mean to you?
What’s something I did that hurt you that we never talked about?
How do you feel about how often we see each other?
What’s one thing I could do this week to make your life easier?

Not sure what makes him feel loved? The love language test is a good start, and it’s fun to do together.

Questions about the future

Better after a few months together. Ask out of curiosity, not to pin him down.

Where do you see yourself in five years?
What’s a big goal you want to reach next year?
Would you rather live in the city or the countryside one day?
Do you want kids, and if so, how many?
How do you feel about getting married?
What would your dream home look like?
Which country would you live in for a year?
What kind of work would make you happy long-term?
Would you ever start your own business?
How important is money to you for feeling secure?
What do you want to experience before you turn 40?
What do you want to learn in the next few years?
What would you want our home to feel like?
What does your perfect retirement look like?
What do you want people to remember about you?

21 questions to ask your boyfriend

21 Questions is a simple game: you take turns asking, both answer every question honestly, and nobody is allowed to skip more than once. These 21 make a good round.

What was your first impression of me?
What’s your biggest fear?
What’s your guilty pleasure?
What’s the best day of your life so far?
What’s a secret talent you have?
Who was your first crush?
What’s the worst date you’ve ever been on?
What’s something you’ve never told your parents?
What’s your biggest pet peeve?
If you could change one thing about your past, what would it be?
What’s the most rebellious thing you’ve ever done?
What’s one thing on your bucket list?
What’s a habit of mine you secretly love?
What’s the last thing that made you really laugh?
What scares you about relationships?
What’s your most controversial opinion?
What’s a place you’d love to show me?
What’s the most important lesson a past relationship taught you?
What would you do if you knew you couldn’t fail?
What’s your favorite thing about yourself?
What do you think our biggest strength as a couple is?

Questions to ask your boyfriend over text

What’s the best thing that happened to you today?
What are you looking forward to this week?
What song are you listening to on repeat right now?
If you could teleport here right now, what would we do?
What made you laugh today?
What’s on your mind right now?
Which photo in your camera roll best sums up your week?
What’s one thing you want us to do this weekend?
What did you dream about last night?

Questions to avoid

Comparisons with his exes. “Was she prettier than me?” has no good answer.
Trap questions asked seriously, like “Would you still love me if I were a worm?”. Fine as a joke, bad as a test.
Questions you don’t want the answer to. If his honest answer would upset you, don’t ask yet.
Everything at once. Twenty deep questions in one evening feels like an interview.

Men and women sometimes hear the same sentence very differently. For a funny look at that, read what men say vs. what women hear. And if you’re looking for the opposite list, here are the questions to ask your girlfriend.