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: September 22, 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?

Section 5 of 7:

Relationship Questions to Ask Your Boyfriend

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Reminisce about your relationship to make him smile. If you’re not sure what to ask, opt for a question about your current or past relationship. This can be a great way to take a walk down memory lane and learn about his priorities within a partnership. Plus, we bet the flow of memories will make you both giggle and blush!
- What was your first kiss like?
- What do you consider couple goals?
- Have you ever had a friend with benefits?
- What was your most awkward date like?
- What’s the worst pick-up line you’ve ever used?
- What’s the most ridiculous thing you’ve done to impress someone?
- What’s your favorite memory of us?
- What’s your idea of the perfect date?^{[10]
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- Do you have a type?
- What’s the most romantic thing you’ve ever done for someone?
- What’s your idea of a perfect proposal?
- Where do yourself in 10 years?
- Do you want kids someday?

Section 6 of 7:

Personal Questions to Ask Your Boyfriend

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Ask about his hobbies, hopes, and loved ones. When in doubt, go for a question that’ll teach you something new about him. Personal questions are great conversation starters. Plus, questions like these can help him open up more. Who knows? Talking about a memory or interest may even bring on a smile.
- What’s your favorite Disney movie?
- Who’s your favorite superhero?
- What’s your favorite musical?
- What’s your favorite book?
- What’s your favorite holiday?^{[11]
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- What’s your favorite movie?
- What’s your favorite food?
- Who’s your favorite artist?
- What’s your favorite season?
- What’s your love language?
- What’s your zodiac sign?
- Where did you grow up?
- What are your aspirations?
- Are you a night owl or an early bird?^{[12]
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- What’s your most obscure hobby?
- How did you meet your best friend?
- What’s your relationship like with your parents?
- Are you a religious person?
- What’s your biggest guilty pleasure?
- What’s one thing you couldn’t survive without?
- What’s your worst habit?
- What do you think is the most interesting thing about yourself?
- What’s one place you’d like to visit?
- Are you an introvert or an extrovert?
- Would you rather stay home or go out?
- What’s your biggest dream?
- What’s your earliest childhood memory?
- What’s your idea of a perfect day?

Section 7 of 7:

Tips for Flirty Communication with Your Boyfriend

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Communicate early and often. Relationship expert Alysha Jeney recommends communicating your romantic needs to your boyfriend right away. Talk to your boyfriend about what turns you on, and ask him what turns him on in return. This way, you know what you both need to do to satisfy each other.
- If you didn’t communicate your needs to him before you became official, do so now. The sooner you talk to one another, the closer you can become.
To show that you’re feeling flirty, Jeney suggests locking eyes with your boyfriend. When your eyes meet, hold his gaze longer than you would an ordinary friend. Think of it as sending a silent plea to make a move or pull you off to be in his arms. The longer the eye contact, the more sexual you feel.
Be spontaneous! When asked how to be romantic with your boyfriend, Jeney responded, “I think spontaneity is always really romantic.” So, ask your boyfriend that random silly or frisky question to keep him interested and engaged. The more you keep him on his toes, the more invested he’ll be in you and the relationship.