150+ Awkward Questions To Ask A Guy You Like

Sometimes the best way to really know someone is by asking questions that make them squirm a little. Awkward questions aren’t about embarrassing someone — they’re about breaking down walls, sparking laughter, and getting real answers you wouldn’t hear otherwise.

Here’s a list of awkward questions to ask a guy — broken down into funny, flirty, and deep. Each one is designed to bring out unexpected, interesting, and sometimes hilarious responses.

Table of Contents

Funny Awkward Questions to Ask a Guy

These are the kind of awkward questions that get him laughing and admitting things he probably wouldn’t share on his own.

Have you ever lied about watching a show just to fit in?
What’s the most embarrassing thing you’ve posted online?
Have you ever sent a screenshot to the person it was about?
What’s the dumbest excuse you’ve used to avoid hanging out?
Have you ever had a crush on your friend’s girlfriend?
What’s the most random thing you’ve bought and never used?
Have you ever Googled yourself?
What’s the weirdest rumor you’ve ever heard about yourself?
Have you ever worn the same outfit twice on purpose because it looked too good?
What’s the worst text you’ve ever sent by mistake?
Have you ever practiced a conversation in the mirror?
What’s the most embarrassing thing you’ve been caught doing alone?

Have you ever lied about liking a song just to impress someone?
What’s the weirdest thing you’ve done when you were bored?
Have you ever been caught stalking someone online?
What’s the most awkward DM you’ve ever received?
Have you ever made a fake excuse and then got caught in the lie?

What’s the most embarrassing thing your parents have walked in on?
Have you ever tried to flirt and it completely failed?
What’s the dumbest injury you’ve ever gotten?
Have you ever waved back at someone who wasn’t waving at you?
What’s your most awkward school memory?
Have you ever been caught liking an old Instagram post?
What’s the worst haircut you’ve ever had?
Have you ever forgotten someone’s name right after they told you?
What’s the weirdest thing in your notes app?
Have you ever had to pretend you understood a joke you didn’t?
What’s the most awkward thing you’ve said on a date?
Have you ever lied about your age?
What’s the cringiest nickname you’ve ever had?
Have you ever laughed in a completely serious situation?
What’s the most awkward family gathering story you have?
Have you ever been caught talking to yourself out loud?
What’s the worst outfit choice you regret?
Have you ever lied to a teacher or boss and instantly regretted it?
What’s the funniest way you’ve embarrassed yourself in public?
Have you ever stalked someone’s profile way too far back?
What’s the weirdest text you’ve woken up to?
Have you ever had food stuck in your teeth all day?
What’s the most awkward compliment you’ve ever received?
Have you ever been caught staring at someone?
What’s the funniest rumor you’ve started (on purpose or not)?
Have you ever pretended not to see someone in public?
What’s the most cringe selfie you’ve ever taken?
Have you ever lied about being busy when you were just watching Netflix?
What’s the weirdest thing you’ve searched on Google late at night?
Have you ever been caught checking someone out?
What’s the dumbest thing you’ve done to try and look cool?
Have you ever been caught singing when you thought no one was listening?
What’s the most awkward silence you’ve ever had with someone?

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Flirty Awkward Questions to Ask a Guy

These ones walk the line between bold and teasing — guaranteed to make him blush a little.

When was the first time you noticed me differently?
Have you ever re-read our texts?
What’s one thing about me that distracts you the most?
Have you ever gotten jealous of someone I mentioned?
Would you kiss me if I asked right now?
What’s the most nervous you’ve felt around me?
Have you ever stalked my profile more than once a day?
Do you secretly talk about me to your friends?
What’s the most attractive thing I’ve done without realizing it?
Have you ever wanted to hold my hand but didn’t?
Do you like it when I tease you?
What’s the cheesiest thing you’ve wanted to tell me?
Do you smile when you get a text from me?
What’s one thing I do that gives you butterflies?
Have you ever thought about cuddling me?
Would you rather I made the first move?
What’s the most awkward crush you’ve had?
Have you ever dreamed about me?
What’s your favorite compliment I’ve ever given you?
Do you think I’d look good in your hoodie?
Have you ever wanted to kiss me in public?
Do you replay our conversations in your head?
Have you ever saved one of my photos secretly?
Do you like when I post selfies?
Have you ever gotten nervous sitting next to me?
What’s the most awkward thing you’ve done around me?
Do you ever wonder if I think about you as much as you think about me?
Would you cuddle me even if people were watching?
Have you ever wanted to text me something flirty but chickened out?
Do you think we’d make a cute couple?
What’s the most awkward thing you’ve wanted to ask me?
Do you notice when I change something about my look?
Have you ever been jealous of someone I was with?
What’s your favorite memory of us so far?
Do you get butterflies when I smile at you?
Would you kiss me on the first date?
Have you ever imagined what our first kiss would feel like?
Do you secretly like when I mess with you?
Have you ever wanted to compliment me but didn’t?
What’s one thing you hope I never find out you think about me?
Do you think about me when you listen to certain songs?
Have you ever been caught staring at me?
Do you find it hard to look me in the eyes sometimes?
Would you rather hold hands or hug?
What’s the most awkward way you’ve tried to flirt with someone?
Do you think I’m more attractive dressed up or casual?
Have you ever wanted to kiss me but didn’t?
What’s the most embarrassing thing you’ve done to impress a crush?
Do you think your friends would like me?
Would you get nervous if I leaned in close right now?

RELATED:

Deep Awkward Questions to Ask a Guy

These ones go beyond surface level — the ones that make him pause before answering.

Have you ever stayed in a relationship you didn’t want to be in?
Do you ever stalk your ex online?
What’s something you’ve done that you still regret?
Have you ever told someone “I love you” and not meant it?
Do you believe in “the one”?
What’s the hardest thing you’ve had to admit to yourself?
Have you ever hurt someone and not apologized?
Do you think you’re hard to love?
What’s one secret you’ve never told anyone?
Have you ever been jealous of a friend?
Do you ever feel like you’re not good enough?
What’s the loneliest you’ve ever felt?
Have you ever ghosted someone and regretted it?
What’s one thing you’d change about your past?
Do you ever pretend you’re okay when you’re not?
Have you ever been in love?
What’s your biggest insecurity?
Do you believe in second chances?
Have you ever ruined a friendship over a crush?
What’s one thing you’ve never told your parents?
Do you ever compare yourself to other guys?
What’s the scariest truth about you?
Have you ever lost feelings and kept it a secret?
Do you think timing matters more than love?
What’s your biggest fear about relationships?
Have you ever felt like someone settled for you?
What’s the hardest goodbye you’ve had?
Do you hide your feelings with jokes?
Have you ever stayed quiet when you wanted to speak up?
What’s one thing you regret saying to someone?
Do you forgive easily or hold grudges?
Have you ever been scared of how much you liked someone?
What’s the most vulnerable moment you’ve had?
Do you believe in love at first sight?
Have you ever been rejected badly?
What’s something you hope nobody ever finds out about you?
Have you ever felt like you weren’t enough for someone?
What’s the biggest risk you’ve taken in love?
Do you think people can really change?
Have you ever lost a friend and regretted it?
What’s one mistake you keep repeating?
Do you think about settling down?
Have you ever hurt someone without realizing it?
What’s the hardest lesson you’ve learned in love?
Do you believe in “right person, wrong time”?
Have you ever lied to protect someone’s feelings?
What’s the most selfish thing you’ve done in a relationship?
Do you think you’ve ever met someone too late?
What’s one thing you hope I never ask you?
Do you think you’ll ever meet someone who really understands you?

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Serena Hansen

Serena Hansen is the creative genius behind the captivating Instagram captions at Swag Captions. As the lead author and content creator, she brings her unique blend of creativity, wit, and insight to every caption, making Swag Captions a go-to destination for those seeking clever and relatable content for their social media posts. Her role at Swag Captions is not just about crafting captions; it’s about curating an experience that resonates with readers and helps them express themselves authentically in the digital world.