100+ Flirty Questions To Ask Your Boyfriend Right Now

So, you’re hanging out with your boyfriend, and you’ve run out of things to talk about—or maybe you’re just curious to dive a little deeper into who he is and what makes him tick. Either way, I’ve got you.

Whether you’re in a new relationship or have been together for years, asking fun, thoughtful, and sometimes even silly questions is such a great way to connect on a deeper level.

Now, I’m not talking about those intense, 3-hour-long life interviews (unless you’re into that!). I mean the kind of questions that spark laughter, open up meaningful conversations, and maybe even reveal something surprising about each other.

From playful “what-if” scenarios to real heart-to-heart stuff, there’s something kind of magical about hearing your boyfriend talk about things he’s never shared before.

So, if you’re ready to learn more about the amazing human you’re dating (and have a ton of fun doing it), keep reading. These questions are your secret weapon to making car rides, late-night texts, and coffee dates way more interesting.

Let’s get into it!

Here are 100+ flirty questions to ask your boyfriend right now!

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Flirty Questions to ask your Boyfriend

Here are some questions to ask your crush when you are already good friends.

• What was your first thought when you saw me?
• Do you ever catch yourself smiling when you think about me?
• What do you think is my most irresistible feature?
• What’s your favorite memory of us so far?
• If we were alone on a deserted island, what would we do first? 😉
• What outfit of mine drives you absolutely crazy?
• Do you like it when I make the first move?
• What’s one thing I do that turns you on instantly?
• Would you rather kiss me slowly for 5 minutes or passionately for 30 seconds?
• Have you ever had a dream about me? What happened in it? 👀
• What do you find sexiest about my personality?
• When was the last time I made your heart race?
• What’s your favorite way to flirt with me?
• Do you like when I tease you, or does it drive you wild?
• Would you rather cuddle under a blanket or go skinny dipping in the ocean?
• If I dared you to kiss me in public, would you?
• What’s something you’ve always wanted to do with me—but haven’t told me yet?
• Do you get jealous when other people flirt with me?
• What part of me do your eyes always go to first?
• If we were to have a “no distractions” date night, what would you want to do?
• What’s the most romantic thing you’ve ever wanted to do with me?
• Would you rather have a long night of cuddles or a passionate make-out session?
• What’s something you’ve wanted to say to me but felt shy about?
• What’s your favorite way to be kissed?
• If I showed up at your door right now, what would you do?
• Have you ever thought about us sneaking away for a weekend? Where to?
• What’s your favorite pet name I call you?
• If we were in a movie, what genre would our love story be?
• What’s something totally innocent I do that drives you crazy?
• If I dared you to write me a flirty text right now, what would it say?
• Do you like it when I play hard to get?
• Would you ever write me a love letter (even if it’s cheesy)?
• If I was your personal genie, what would your three wishes be?
• Have you ever imagined our first time? 😏
• What’s one song that always makes you think of me?
• Would you rather stare into my eyes or kiss my lips?
• What’s your idea of the perfect kiss?
• When we’re not together, what do you miss the most?
• Have I ever made you blush?
• What’s one thing you’d love for me to whisper in your ear?
• Do you like when I surprise you with flirty messages?
• What’s your favorite kind of physical affection?
• If I challenged you to a flirty game night, what game are we playing?
• Have you ever wanted to sneak a kiss when we were around others?
• What’s your favorite way I show you love?
• If we were dancing alone in a room, what song would you want playing?
• What’s something naughty you’ve imagined us doing together?
• What do you want to wake up next to tomorrow—besides me? 😏
• Would you rather have a hot kiss in the rain or under the stars?
• How do you want me to surprise you next time we meet?

Juicy questions to ask your boyfriend

Here are some deep questions to ask your crush.

• What was your first thought when you saw me?
• Do you ever catch yourself smiling when you think about me?
• What do you think is my most irresistible feature?
• What’s your favorite memory of us so far?
• If we were alone on a deserted island, what would we do first? 😉
• What outfit of mine drives you absolutely crazy?
• Do you like it when I make the first move?
• What’s one thing I do that turns you on instantly?

• Would you rather kiss me slowly for 5 minutes or passionately for 30 seconds?
• Have you ever had a dream about me? What happened in it? 👀
• What do you find sexiest about my personality?
• When was the last time I made your heart race?
• What’s your favorite way to flirt with me?
• Do you like when I tease you, or does it drive you wild?
• Would you rather cuddle under a blanket or go skinny dipping in the ocean?
• If I dared you to kiss me in public, would you?
• What’s something you’ve always wanted to do with me—but haven’t told me yet?
• Do you get jealous when other people flirt with me?
• What part of me do your eyes always go to first?
• If we were to have a “no distractions” date night, what would you want to do?
• What’s the most romantic thing you’ve ever wanted to do with me?
• Would you rather have a long night of cuddles or a passionate make-out session?
• What’s something you’ve wanted to say to me but felt shy about?
• What’s your favorite way to be kissed?
• If I showed up at your door right now, what would you do?
• Have you ever thought about us sneaking away for a weekend? Where to?
• What’s your favorite pet name I call you?
• If we were in a movie, what genre would our love story be?
• What’s something totally innocent I do that drives you crazy?
• If I dared you to write me a flirty text right now, what would it say?
• Do you like it when I play hard to get?
• Would you ever write me a love letter (even if it’s cheesy)?
• If I was your personal genie, what would your three wishes be?
• Have you ever imagined our first time? 😏
• What’s one song that always makes you think of me?

• Would you rather stare into my eyes or kiss my lips?
• What’s your idea of the perfect kiss?
• When we’re not together, what do you miss the most?
• Have I ever made you blush?
• What’s one thing you’d love for me to whisper in your ear?
• Do you like when I surprise you with flirty messages?
• What’s your favorite kind of physical affection?
• If I challenged you to a flirty game night, what game are we playing?
• Have you ever wanted to sneak a kiss when we were around others?
• What’s your favorite way I show you love?
• If we were dancing alone in a room, what song would you want playing?
• What’s something naughty you’ve imagined us doing together?
• What do you want to wake up next to tomorrow—besides me? 😏
• Would you rather have a hot kiss in the rain or under the stars?
• How do you want me to surprise you next time we meet?

Romantic questions to ask your boyfriend

• When did you first realize you loved me?
• What’s your favorite memory of us?
• How has our relationship changed you?
• What do you love most about being with me?
• What’s something special about us that you’ve never felt with anyone else?
• Do you believe we were meant to meet?
• What’s one thing you want us to do together that we haven’t yet?
• How would you describe our love story?
• What moment made you feel closest to me?
• Do you think we bring out the best in each other?
• What’s your favorite way to show love?
• What’s your favorite way I show you love?
• When do you feel most loved by me?
• Do you enjoy cuddling more in the morning or at night?
• What’s the sweetest thing I’ve ever done for you?
• What’s the most romantic thing you’ve ever wanted to do for me?
• What’s your favorite thing I’ve said to you?
• Do you like love notes or surprise kisses more?
• What do you feel when we hug?
• How often do you think about me during the day?
• What’s your favorite compliment I’ve ever given you?
• What’s something about me you’ll never get tired of?
• Is there a little thing I do that always makes you smile?
• What do you admire most about me?
• What’s one thing you think I don’t realize you love about me?
• What makes you proud to be with me?
• What do you think makes me beautiful inside and out?
• When you introduce me to people, what do you say about me?
• What’s your favorite photo of us?
• What’s one thing you’d never change about me?

• What’s your dream date night with me?
• Where do you see us in five years?
• If we could live anywhere together, where would you choose?
• What’s one future milestone you’re excited to share with me?
• Do you think we’ll grow old together?
• What kind of home do you imagine us building?
• What’s your dream vacation with me?
• What’s one tradition you’d love us to start?
• What do you want our love to look like years from now?
• How do you think we’ll celebrate our anniversary in the future?
• What does intimacy mean to you?
• When do you feel the most emotionally connected to me?
• Do you feel like you can tell me anything?
• What helps you feel safe in our relationship?
• What’s something you’ve told me that you’ve never shared with anyone else?
• Is there anything about love that you learned from being with me?
• When did you feel most emotionally vulnerable with me?
• What do you think brings us closer together?
• Do you feel like I truly understand you?
• What’s something you love about the way we communicate?

More Flirtly questions to ask your Boyfriend

• What would you do if I kissed you right now?
• What’s your idea of the perfect romantic surprise from me?
• If I showed up at your place wearing your shirt and nothing else, what would you say?
• What’s the most attractive thing someone could wear—to you?
• Do you like when I catch you staring at me?
• What’s one thing you’ve imagined doing with me but haven’t told me yet?
• If I said I wanted to kiss you all over, where would you want me to start? 😏
• Would you rather flirt over text or in person?
• What’s one thing I could say that would totally melt you?
• How do you feel when I call you mine?
• What do you think when I bite my lip—or is that just in movies? 😜
• Would you rather cuddle all night or sneak off for some trouble?

• What’s your favorite kind of flirting—playful, subtle, or bold?
• Do you ever think about kissing me in random places? Like the elevator or a parking lot?
• What’s the most romantic spot you’d love to take me to (and maybe steal a kiss)?
• Do you think I look cuter when I’m dressed up or in my pajamas?
• Have you ever tried to impress me without me knowing?
• If we had a lazy Sunday in bed, what would you want to do all day?
• What’s one compliment from me that always makes you blush?
• Do you like when I get a little jealous?
• What’s your favorite memory of us kissing?
• If I dared you to kiss me without using your hands, would you accept the challenge?
• What’s one place on your body you wish I’d touch more often?
• What do you think about when you miss me?
• If I let you plan a “no rules” date night, what are we doing?
• What’s the one thing I do that drives you crazy in the best way?
• Do you like when I playfully tease you—or does it make you want to get even? 😈
• What’s one secret desire you’ve never told me?
• If I whispered something naughty in your ear, would you keep a straight face?
• Do you like slow, intense kisses or quick, playful ones?
• What’s your guilty pleasure when it comes to me?

The Bottom Line:

And there you have it—some seriously fun and meaningful questions to ask your boyfriend that go way beyond “what’s your favorite color?”

Whether you’re cuddled up on the couch, killing time on a road trip, or just texting each other during a busy day, these questions are perfect for keeping the spark alive and really getting to know one another.

Remember, it’s not just about asking the question—it’s about listening to the answers, laughing together, and letting the conversation flow naturally.

Some answers might surprise you, some might make you laugh till you cry, and others might bring you even closer than before. That’s the beauty of it.

So go ahead, bookmark this post or save it for later—because anytime is a good time to spark a deeper connection with the person you love.

Got any cute or unexpected answers from your boyfriend? I’d love to hear about them—drop them in the comments!