Looking to spice up your next hangout with some awkward and hilarious moments?
Sometimes, the best way to break the ice and create memorable memories with your friends is by asking questions that make everyone squirm a little.
Whether you’re playing a game, trying to make someone blush, or just in the mood for some quirky fun, these 110 embarrassing questions will do the trick.
From questions about crushes and embarrassing moments to the things we’ve all wondered but never dared ask, this list will keep everyone laughing (and a little uncomfortable).
So, grab your friends, get ready for some awkward silences, and dive into these hilarious questions!
Hilarious and Awkward Questions to Ask Friends for a Fun
1. What’s the most embarrassing thing you’ve done while trying to impress someone?
We’ve all been there, trying way too hard. Time to spill the beans!
2. Have you ever sent a text to the wrong person? What did it say?
Texting fails are classic embarrassing moments. Who was the victim of your accidental message?
3. What’s the most embarrassing thing you’ve Googled?
We all have that one embarrassing search history moment. Go on, admit it!
4. Have you ever accidentally walked into the wrong bathroom?
Oops! Hopefully, you caught it before anyone noticed…
5. What was your most awkward first date experience?
First dates are full of cringe-worthy moments. What’s your most memorable?
6. Have you ever had a wardrobe malfunction in public?
From ripping pants to unzipped flies, we’ve all experienced a wardrobe mishap.
7. What’s something you’ve done that you still can’t believe you did?
Everyone has those moments they wish they could erase. Spill!
8. Have you ever accidentally farted in public and blamed it on someone else?
Who hasn’t tried to play it off when nature calls a little too loudly?
9. What’s the most embarrassing thing you’ve ever said to your crush?
Crushing hard sometimes leads to saying the dumbest things.
10. Have you ever tried to act cool and totally failed? What happened?
Trying to be smooth and failing is a rite of passage. Share your stories!
11. What’s the weirdest dream you’ve had that you can remember?
Some dreams are so strange, they leave us questioning our sanity. What’s yours?
12. Have you ever gotten caught talking about someone, only to realize they were right behind you?
Nothing beats the feeling of realizing you’re talking behind someone’s back… and they’re right there.
13. What’s the most awkward situation you’ve ever been in with your parents?
From uncomfortable conversations to embarrassing incidents, parents can create the ultimate cringe moments.
14. Have you ever sent a risky text to your ex? What happened after?
We all have that one “oops” moment with an ex. Spill the tea!
15. What’s the most embarrassing thing you’ve ever done while drunk?
It happens. Maybe it’s time to come clean!
16. Have you ever had a crush on someone who had no idea you existed?
Crushing from a distance can be painfully awkward. Share your experience!
17. What’s the worst lie you’ve ever told to get out of something?
Sometimes, we have to get creative to avoid uncomfortable situations. What’s your best (or worst) lie?
18. Have you ever been caught singing in the car or shower, but didn’t realize someone was watching?
Let’s face it, we’ve all had our moments of thinking we’re rockstars.
19. What’s the most awkward thing that’s ever happened during a job interview?
Interview disasters are all too real. Any embarrassing moments you’d like to share?
20. Have you ever tripped in public and pretended like it didn’t happen?
Who hasn’t played it cool after a faceplant?
21. What’s the weirdest thing you’ve ever done for attention?
We all do strange things to stand out sometimes. What was your “look at me” moment?
22. Have you ever been caught texting something inappropriate to the wrong person?
Mistakenly texting something personal to the wrong person is a classic!
23. What’s the weirdest food combination you secretly love?
Sometimes our food cravings get a little… questionable. What’s your guilty pleasure?
24. Have you ever had a crush on someone’s sibling? What happened?
Crushing on a friend’s sibling? That’s a level of awkward nobody prepares you for.
25. What’s the most embarrassing thing you’ve done in front of a teacher?
We’ve all embarrassed ourselves in school—what’s your most cringe-worthy moment?
More Embarrassing Questions to Keep the Fun Going:
- Have you ever said something awkward during a speech or presentation?
- What’s the worst thing you’ve ever done to get out of a family event?
- Have you ever lied about being sick to avoid a hangout?
- What’s the most embarrassing thing you’ve done while meeting someone new?
- Have you ever been caught in an awkward silence with your crush?
- What’s something embarrassing that still haunts you to this day?
- Have you ever accidentally flashed someone?
- What’s the most embarrassing childhood memory you still remember?
- Have you ever called someone by the wrong name during an intimate moment?
- What’s the dumbest thing you’ve ever done to impress a friend?
- Have you ever fallen asleep in public and drooled?
- What’s the most embarrassing thing you’ve ever said to your parents?
- Have you ever tried to hide a fart by making another noise?
- What’s the most awkward thing you’ve overheard someone say about you?
- Have you ever been caught doing something you thought you were doing in private?
- What’s the most embarrassing thing you’ve done on social media?
- Have you ever used the wrong emoji in a text?
- What’s the silliest thing you’ve ever done because you were nervous?
- Have you ever kissed someone and realized it was a huge mistake?
- What’s the most embarrassing thing you’ve done at a wedding?
- Have you ever texted an emoji that didn’t match your mood?
- What’s something you’ve done that you wish no one would ever find out?
- Have you ever gotten caught staring at someone for too long?
- What’s the funniest thing you’ve done to make someone laugh, but it backfired?
- Have you ever been caught doing something you were embarrassed to admit?
- Have you ever tried to talk to someone with food in your teeth and didn’t realize?
- What’s the most awkward thing that’s ever happened during a group photo?
- Have you ever kissed someone and felt totally weird about it afterward?
- What’s the most embarrassing thing you’ve done while trying to be “cool”?
- Have you ever farted and tried to blame it on an animal or inanimate object?
- What’s the silliest reason you’ve ever gotten into an argument with a friend?
- Have you ever been caught singing loudly in public, thinking no one was around?
- What’s the worst haircut you’ve ever had?
- Have you ever accidentally sent a personal message to a group chat?
- What’s the most embarrassing thing you’ve done while trying to be romantic?
- Have you ever gotten caught trying to sneak food into a movie theater?
- What’s the weirdest fashion trend you’ve ever followed?
- Have you ever been caught texting someone you were gossiping about?
- What’s the most awkward moment you’ve had in an elevator?
- Have you ever had an awkward encounter with your best friend’s parents?
- What’s the funniest thing you’ve done to avoid awkward small talk?
- Have you ever used the wrong emoji, and it caused an awkward situation?
- What’s the most embarrassing thing you’ve done while under the influence?
- Have you ever laughed at something you didn’t really find funny, just to fit in?
- What’s the most awkward thing you’ve done in a job interview?
- Have you ever gotten caught picking your nose in public?
- What’s the dumbest thing you’ve done in front of someone you were trying to impress?
- Have you ever accidentally walked into the wrong room at someone’s house?
- What’s the weirdest thing you’ve done to try to make someone laugh?
- Have you ever had a crush on someone who turned out to be really embarrassing?
- What’s the most awkward thing you’ve overheard someone say about you?
- Have you ever had a cringy encounter with someone you used to date?
- What’s the weirdest dream you’ve had about a friend?
- Have you ever accidentally liked an old photo on someone’s Instagram while stalking them?
- What’s the worst text you’ve sent to someone in the middle of a fight?
- Have you ever tried to tell a joke and no one laughed?
- What’s the most embarrassing thing you’ve done while traveling?
- Have you ever been caught doing something you were trying to hide from your parents?
- What’s the weirdest thing you’ve done to try and get attention from someone?
- Have you ever sent a text that you instantly regretted?
- What’s the most embarrassing thing you’ve done while introducing someone?
- Have you ever been caught checking someone out in public?
- What’s the most awkward conversation you’ve had with a stranger?
- Have you ever done something embarrassing at a family gathering?
- What’s the silliest reason you’ve ever gotten mad at someone?
- Have you ever tripped over your own feet and pretended you were dancing?
- What’s the most embarrassing thing you’ve ever done in front of your crush?
- Have you ever accidentally said something inappropriate at a formal event?
- What’s the worst thing that’s ever happened when you tried to cook for someone?
- Have you ever gotten caught trying to sneak a nap in the middle of the day?
- What’s the most embarrassing social media post you’ve ever made?
- Have you ever forgotten someone’s name right after being introduced?
- What’s the most awkward encounter you’ve had while on a date?
- Have you ever been caught texting something meant for someone else?
- What’s the funniest thing you’ve said when you were really nervous?
- Have you ever gotten caught doing something embarrassing in front of a coworker?
- What’s the weirdest excuse you’ve used to avoid going somewhere?
- Have you ever told a lie to get out of an awkward situation?
- What’s the most embarrassing thing you’ve done at a party?
- Have you ever said something embarrassing in front of a large group of people?
- What’s the weirdest habit you have that you’re embarrassed to admit?
- Have you ever accidentally texted a compliment to the person you were talking about?
- What’s the worst thing you’ve done to get out of a commitment?
- Have you ever made a fool of yourself by sending a late-night text?
- What’s the most embarrassing thing you’ve done when you thought no one was watching?
Final Thoughts
Now you have 110 awkward questions to ask your friends!
From cringe-worthy texting fails to funny and embarrassing situations we’ve all experienced, these questions are perfect for sparking hilarious, albeit awkward, conversations.
Whether you’re looking to break the ice, create unforgettable moments, or just laugh at each other’s misfortune, these questions will definitely keep the fun (and the awkwardness) flowing.
So, grab your friends and start asking these awkward questions—you might just learn something new (or embarrassing) about each other!