150+ Romantic & Funny Questions to Make Your Boyfriend Laugh

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Tickle your BF’s funny bone & start a sweet conversation with these clever questions

Co-authored by Alysha Jeney, MA, LMFT and Aly Rusciano

Last Updated: May 31, 2024 Fact Checked

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Flirty & Romantic Questions

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Funny Questions

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Dirty Questions

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Deep Questions

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Relationship Questions

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Personal Questions

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Tips for Flirty Communication

Gosh, you really like your boyfriend. Like, really like him, and you just want to hear his laugh all day, every day! Are there things you can ask him to get him to laugh more? Luckily, there are! From flirty remarks to funny scenarios, we have all the conversation starters you can ask him right here. We even chatted with relationship expert Alysha Jeney to bring you the best advice when it comes to flirting and talking to your boyfriend. Take a look at the list below to see what romantic questions you can ask your boyfriend to make him laugh.

Questions to Ask Your Boyfriend

What’s your favorite thing about me?
What’s your favorite memory of us?
What’s the worst pick-up line you’ve ever used?
What reality TV show do you think you would win?
What’s the dirtiest dream you’ve ever had?

Section 1 of 7:

Flirty & Romantic Questions to Ask Your Boyfriend

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Keep him on his toes with a question that’ll make him blush. If you’re feeling confident, toss him a flirtatious remark to make him smile. This is a great way to see if he’s also feeling flirtatious, all while inadvertently saying, “Hey, I still like you.” Try using one of these questions to get started:
- Do you think you’re a good kisser?
- Where is your favorite place to be kissed?
- When do you feel your sexiest?
- Do you have a go-to pick-up line? ^{[1]
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- What’s your favorite thing about me?
- How do you feel when I kiss you?
- What name do you secretly call me?
- What would you cook me for dinner?
- If you could ask me anything, what would it be? ^{[2]
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- Have you ever dreamt about me?
- Do you ever make the first move?
- If I were a flower, what flower would I be?
- Do you consider yourself romantic?
- What’s your favorite love song?
- What’s the perfect way to ask someone out?
- How do you envision our future together?
- What do you find attractive about me?
- What song do I remind you of?
- What’s your ideal night in?
- Have you ever fantasized about me?

Section 2 of 7:

Funny Questions to Ask Your Boyfriend

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Lighten the mood with a question that will make him chuckle. Think about the most absurd and random thing you can ask him, and then ask away! Not only is this a great conversation starter, but it’s also an excellent way to have fun together.
- What’s the weirdest thing in your search history?
- What’s the dumbest injury you’ve had?
- What’s the weirdest thing you believed growing up?
- What’s the strangest dream you’ve ever had?
- If you could only eat one food for the rest of your life, what would it be?
- What fictional character do you wish was real?
- What’s the funniest thing you’ve seen on social media?
- Do you have any weird talents?
- What’s the wildest fashion trend you tried?
- What’s the funniest text you’ve gotten? ^{[3]
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- Which Disney character are you most like?
- If you could have any pet, what would it be?
- Do you believe in aliens?
- Who would you haunt if you were an animal?
- What superhero powers would you have?
- Sneakers or sandals?
- Who would play you in a movie about your life?
- Which historical figure would you invite to dinner?
- Which celebrity would you want to go to a concert with?
- What’s the silliest video you’ve ever seen?
- If you could only have one app on your phone, what would it be?
- What’s your favorite meme?
- Mustard or ketchup? ^{[4]
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- If you were a sandwich, what sandwich would you be?
- What’s your least favorite word?
- What reality TV show do you think you would win?
- If you could live in another decade, what decade would you live in?
- What’s the most ridiculous thing you’ve ever bought?
- What’s the worst joke you've ever heard?
- What would you do if you won the lottery?
- Would you rather have a giant dog or cat?
- What would your last meal be? ^{[5]
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- If you went to prison, what would it be for?

Section 3 of 7:

Dirty Questions to Ask Your Boyfriend

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Get your boyfriend to laugh with a risque comment. What better way to keep him on his feet than with a question he would never see coming? Toss him a dirty joke, cheeky compliment, or frisky question if you’re feeling sexy.
- Do you sleep naked?
- Do you imagine me naked when we’re apart?
- What celebrity would you sleep with?
- Are you a part of the mile-high club?
- What’s the dirtiest dream you’ve ever had?
- Do you prefer the lights on or off?
- Which body part is your favorite?
- What’s your biggest turn-on?
- What’s your biggest turn-off?
- What’s your kink?
- Have you ever role played before?
- Have you ever played strip poker?
- What’s your biggest fantasy?
- What’s your favorite position in bed?
- What’s your favorite type of kiss?
- What’s your favorite toy to use in the bedroom?
- Where’s your favorite place to have sex?
- What’s on your sexual bucket list? ^{[6]
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- Do you prefer rough or gentle sex?
- What type of person turns you on?
- If you were a stripper, what would your name be?
- What’s the dirtiest thing you’ve ever done?
- Have you ever had a one-night stand?
- Have you ever been skinny dipping?

Section 4 of 7:

Deep Questions to Ask Your Boyfriend

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Dive under the surface to get to know him better. If you’re in a committed relationship, you may be past small talk. In that case, it’s totally okay to dig a little deeper—he may even be expecting you to! Think about what you really want to know about him, and then ask away (just be prepared to answer the same question in return).
- What do you wish people knew about you?
- Do you believe there’s life after death?
- What’s the best piece of advice you’ve gotten?
- What’s your favorite childhood memory? ^{[7]
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- Have you ever cheated on someone?
- How many times have you been in love?
- Do you believe in gut feelings?
- What makes you feel old?
- What do you wish you could change about yourself?
- Who’s your biggest role model?
- Do you believe in soulmates?
- When was the last time you cried? ^{[8]
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- Do you want to be more or less like your parents?
- Would you ever take back a cheater?
- What’s something you’ve always wanted to learn?
- What are you most proud of?
- What’s a habit you’d like to break?
- If you could go back in time, what would you change?
- What inspires you?
- What was your most embarrassing moment like?
- What’s your biggest fear? ^{[9]
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- What are you willing to die for?
- Do you believe in karma?
- Do you think you’re a good person?
- What would you do if you had 24 hours to live?
- What’s your opinion on social media?
- What’s your communication style?
- What’s your idea of a perfect life?
- What are your top 3 priorities?
- What are your goals for the future?
- What’s your definition of success?
- What’s your biggest regret?