Couples Questions

195 Fun Questions To Ask Your Boyfriend

February 8, 2023

Whether you’ve only been with your boyfriend for a short time or the two of you have already reached milestone anniversaries, there’s always room to learn more about each other. Research shows disclosing our hopes, beliefs, turn-ons, mistakes, and more with our partner (self-disclosure) is linked to higher relationship quality and lower divorce rates (Finkel, 2017). That means the more questions you ask, the more you bond, which increases vulnerability (which is a good thing!) and trust between the two of you. Plus, having an open conversation about things the two of you have possibly never discussed beats yet another date night of takeout in front of the tv.

Below, we’ve provided some fun questions guaranteed to get your boyfriend talking, laughing, and sharing stories. Want more? Download Lovewick’s free couples card game for iOS and Android for 1000+ questions and hundreds of date ideas!

Note: Not all questions will be appropriate for every relationship, so feel free to mix and match questions according to your situation. Use these questions in various settings and situations: while waiting at the airport, sitting on the couch together, or even during a road trip.

Questions To Ask Your Boyfriend To Get To Know Him Better

Depending on the length of your relationship, you might think you know almost everything about the person you spend most of your time with. You may know his favorite movie, favorite drink, what kind of music he likes, his favorite animal, and even what toppings he likes most on his hamburger. If you don’t know these yet — hey, that’s ok, too!

That said, knowing favorites doesn’t get into the “why” behind them, so if you’re looking to go a layer deeper and beyond one-word answers, we’ve compiled a list of our favorite personal questions to learn more about your boyfriend’s life, his thoughts, and his values. Draw out interesting stories about your boyfriend’s past before you met (like embarrassing moments he might have forgotten) or unlock new aspects of his personality you perhaps haven’t seen yet.

Would you rather be able to temporarily turn off your thoughts or turn off your feelings?
Do you think people are born “good” or have to learn to be?
What does the world need more of right now: love, truth, or something else?
What’s the biggest thing holding society back right now?
How do you feel about having an emotionally charged discussion late at night vs. letting it go until the morning?
What was valued more in your family growing up: making decisions with your heart or with your head?
Do you see yourself as more practical or creative?
What fact did you learn at an embarrassingly late age?
What would be in your dream secret lair/private space just for you?
What’s the most embarrassing thing on your bucket list?
Who do you spend the most time with, and what do you think it says about you?
What’s more important to you: safety or freedom?
What’s the hardest thing you’ve ever done, physically?
Would you rather have free passes to all amusement parks or all concerts?
If you could do something dangerous just once with no risk, what would you do?
Who are you most afraid of?
What chore do you find most frustrating?
What chore do you absolutely love (or least find pleasure in)?
If you had to outlaw something right now, what would you choose for the betterment of the world?
What do you believe is more important: real-life experience or imagination?
What was your childhood nickname?
What is your earliest childhood memory?
What’s your least favorite holiday, and why?
What’s your useless hidden talent?
If you could have a button in your life that would do one thing every time when pressed, what would it do?
What was your most embarrassing moment?
If you got a billboard in Times Square for 48 hours, what would you put up there?
Where does “what’s mine is yours” cross the line for you?
Where would you go for vacation if money was no object?
Do you wish you had more or less freedom growing up? Why?
What’s one thing about you that you consider private, and you have to be very comfortable with another person to show/say?
What’s the most significant way you think other people waste money?
What’s the worst thing about being a wedding guest?
What are you really good at fixing?
If you could read one person’s mind, who would you choose?
What dish would you pick if you had to eat the same food for the rest of your life?
What are some reasons you would unfollow or block someone?
Which cartoon character were you obsessed with growing up?
What were you like in high school? Do you think we would have gotten along?
How did you feel about your first kiss?
For what things do you or would you spare no expense?
What personal habit are you most proud of?
What do you feel least insecure about?
Were your parents too strict, or not strict enough?
What’s your biggest pet peeve? What about the silliest pet peeve?
Do you prefer to be left alone or to have someone cheer you up when you’re in a bad mood?
How do you feel about picking out an outfit every day?
Which of your friends is most like you?
Do you think it’s fair to split bills 50/50 even if one person in the relationship makes significantly more money?
What was your weirdest wrong number text or call?
Would you rather have to speak in front of a huge audience every day or get a visible tattoo you really hated?
Were you raised to put your partner or your kids first?
What is the best advice you’ve been given about dating and relationships?
What always makes you laugh out loud?
What’s the most you’ve spent at a restaurant?
What’s the grossest thing you’ve found in your house?
What’s on your anti-bucket list, a list of things you never want to do again?
Would you rather be a food critic or a film critic?
What advice from a family member or friend has stuck with you the most?
Who in your life would you say has the most positive outlook? How so?
What does your “me-time” look like?
Would you rather be an amazing artist or a brilliant mathematician?
What music makes you feel alive?
What was your go-to childhood snack?
What’s something you used to be really into that you aren’t anymore?
In what way are you most predictable?
What does “quality time” mean to you? Is it more than being in someone’s company?
What are the first three things you’d buy for your dream mansion?
Would you rather know when you’re going to die or how you’ll die (you can’t change the time or method of death)?
What’s one thing that makes someone instantly interesting to you?
What’s the craziest thing you’ve done on a dare?
Would you rather go streaking or skinny-dipping?
What’s the weirdest thing you’ve ever witnessed a stranger?
What’s the longest you’ve ever been on the phone, and who were you talking to?
Would you rather have an unlimited international first-class ticket or never have to pay for food at restaurants?
Would you rather have endless time or endless money?
What do you believe should be free but isn’t? Why?
What crazy things have you done while out with friends?
What’s the most expensive thing you’ve ever held in your hand(s)?
What’s one of your family or friend group’s classic stories?
Do you think sexuality is a spectrum or more black-and-white? Where do you think that belief came from?
What’s the most disturbing thing someone has said to you?
What’s the most embarrassing thing you were doing ten years ago?
What tradition would you most like to pass on to your children?
What’s something that you feel is better to do alone?
Who was your favorite teacher in school, and why do you remember them so fondly?
What is your favorite unsolved mystery?
Apart from cheating, what is inexcusable in a relationship?
Is your default to be more inwardly focused or outwardly focused?
Has a stranger ever bought you a drink? What’s the story?
What are three things you think about every day?
If a stranger randomly texted you and asked for advice, would you give it or not reply?
What’s one difference you’ve noticed between you and your partner’s morning or evening routines?
What, if anything, would be worth taking out a loan for?
What movie sidekick would you most want for your best friend?
Would you rather be stuck in a library and have the ability to speed read or stuck in a casino with $10k to play?
Would you rather Instagram Live your whole day or be mute for a day?
Would you rather have a life rewind, pause, or fast-forward button?
In what ways, if any, was your family untraditional?
Have you ever hopelessly failed at something? If so, what?
If your personality were a store in the mall, which would it be and why?

Fun Questions To Ask Your Boyfriend About You

Part of the fun of asking your boyfriend these questions will be learning what he thinks about you. Even if he’s mostly open about his feelings, some questions and hypotheticals have likely never come up in conversation. Maybe you want to know how he felt the first time the two of you kissed or shared your feelings, or perhaps there are some fond memories he hasn’t reminisced about with you because he hasn’t found the right opening or opportunity yet.

Don’t worry; here are a few fun questions to get you started:

What’s something you do with me that makes you especially happy?
What’s your favorite memory of me so far?
How can I be a better partner to you?
When do you feel closest to me?
If I had a catchphrase, what would it be?
What do I do that makes you feel loved or cared for?
Does anything about me intimidate you?
Do you feel like I’m consistent enough at showing that you’re important to me?
If my personality were a musical instrument, which would it be and why?
What’s something new that I’ve helped you experience?
What’s the most attractive thing I’ve worn out?
What was your first impression of me?
What’s something I do that makes you feel safe?
What was the funniest thing you ever saw me do?
What’s my sexiest feature?
What could I do to make your day easier?
Do you ever dream about me?
When have you felt the proudest of me?
If you were to make a playlist about me, what kinds of songs would you put on it?
What’s something I do that always makes you feel loved?
What’s my best quality, and why does it attract you?
Which fictional character reminds you of me in real life?
Do I have any quirky habits that you find endearing?
What’s the best gift I’ve ever given you?
What’s the most stress-relieving thing I’ve done for you?
Do you remember the moment that you knew that you wanted to be with me or loved me?
What’s a question you’ve always wanted to ask me but never have?
What’s the best thing I’ve cooked or made for you?
What do you think I think most in a day?
What’s the picture of me you show your friends when talking about me?
Who else in your life do I remind you of most?
What’s your favorite way to spend time with me?

Fun Questions To Ask Your Boyfriend About Your Relationship

When you ask your boyfriend deep questions about your relationship, it helps open the two of you up to all sorts of different ways to communicate your feelings. You can learn what he likes about the relationship and what the two of you can work on to communicate better and be more open with one another.

If you were writing an autobiography, what would you call the chapter when our lives intersect?
What is your favorite thing about our relationship?
What makes us different from other couples?
What do you think your younger self would think of our relationship?
What movie title could describe our relationship?
What’s the biggest thing holding our relationship back from being happier?
How and when did you know we’d be a great couple?
What’s your favorite memory of us?
Why did you decide to start a relationship with me?
What do you wish I did more in our relationship?
Do you feel like we spend enough time with each other’s family and friends?
What single word describes our relationship?
What aspect of our relationship makes you the happiest?
If we met again for the first time, but with all the knowledge of our relationship up to now, what would you want to say to me?
How would you describe our first date?
Which habits have we picked up from one another?
What would be the best thing about growing old with me?
What does each of us do right in our relationship?
What quirky thing do you love about our relationship?
How would you describe our relationship to a stranger?
If you could relive one day together, which would it be?
What’s something you look forward to doing with me in the near future?
What’s one thing we always disagree on but also laugh about?

Flirty Questions To Ask A Guy

Whether you’re crushing, dating, or even married, flirting remains one of the best parts of a relationship! It’s a fun, playful way to bring excitement into your relationship.

What Makes A Good Flirty Question?

Flirty questions should be fun, engaging, and a little bit silly! Something that requires a little thought and creativity is usually the best. When choosing flirty questions, try to stay away from anything serious, negative, or inappropriate. Questions should have a little bit of sexual innuendo, but not too much. Flirting is all about balance!

If you’re looking for something a little spicier, we’ve included plenty of juicy questions for that later!

Flirty Questions

Here are some good flirty questions to ask your boyfriend:

Would you rather kiss in the moonlight or kiss in the rain?
Do you like cuddling or kissing more?
To what extent is hand-holding important to you?
What’s the most romantic movie scene you’ve watched?
What is your favorite place on your body to be kissed?
What’s your favorite physical feature of your own? Why?
Where would you like me to touch you more?
How do you feel about showering or bathing with me?
What’s something you love about how I kiss you?
What do you remember the most about our first kiss?
What outfit do you think I look the sexiest in? Why?
Do we cuddle enough? What’s your favorite cuddling position?
What area on your body (non-sexual) do you love getting massages?

Juicy Questions To Ask Your Boyfriend (NSFW!)

If you want to spice things up with more intimate questions, try these 13 juicy questions to ask your boyfriend. These questions are pretty revealing, so tread carefully. If he’s uncomfortable answering these, try to be understanding and not take it personally — people move at different paces. These questions are probably for couples who have been together for a longer time and know each other fairly well.

What’s your favorite place we’ve been intimate? Why?
What makes you feel our connection the most when we are being intimate?
Who would be the third in your fantasy threesome? Why?
How do you feel about role play in the bedroom? What’s a character, if any, that sounds fun?
Imagine a perfectly designed room for a sexy night for us together. What does it look like?
What’s your favorite part of foreplay? Why?
How do you feel about licking, biting, and pinching?
What’s your favorite part of giving? What about receiving?
Is there anything in the bedroom that we haven’t tried that you’d like to discuss?
Which of the five senses is the most sexual to you?
What’s your favorite sexy memory of us?
Ideally, how often would you like to have sex?
What “gets you in the mood” that I may not know about?

Romantic Questions To Ask Your Boyfriend To Make Him Laugh

Whether you’re together, killing time while you’re at work and thinking about him, or just bored and want to feel an awkward silence, we have questions for those situations as well!

Sometimes you want to ask questions just to be silly and laugh with each other because you’re bored, and that’s okay! Asking questions doesn’t always have to lead to some monumental reveal about their personality; sometimes, it’s fun to just, well, have fun. Here are some silly questions to get you started!

If we were together on any reality tv show, which one would you choose, and what would you do to win?
What were your silliest nicknames growing up?
Would you let me use your toothbrush?
How would we fare in a zombie apocalypse?
If our lives were a TV show, what tropes would we be?
What’s the cringiest “pet name” you can think of for me?
Is there a silly accomplishment in our relationship you’re secretly proud of?
What’s the most hilarious thing you’ve walked in on me doing?
Would you rather rescue me from aliens or the mob?
What would the class title be if you taught a university course about our relationship?
If we swapped bodies like in Freaky Friday, what would you do?
What would your family and friends assume you had done if you were arrested with no explanation?
What’s the most ridiculous, over-the-top date idea you can come up with right now?

Get 1,000 More Questions – Free!

Lovewick’s couples questions are the perfect way to get to know your partner on a deeper level! By answering questions that may not come up in day-to-day life, you and your partner can bond on a deeper level. Get Lovewick’s free relationship app for couples on iOS or Android, and start playing today!