These Are 23 Of The Most Uncomfortable Questions You Can Ask

There are plenty of awkward questions you’d love to ask people if given the chance. But unfortunately social queues and common decency require that you don’t, because you know that those questions are hella inappropriate.

Many people still don’t realize what questions should always be off limits. Like, you shouldn’t ask a woman if she’s pregnant in the off chance that she’s just fat. There are some that acknowledge questions like these are inappropriate and stay far away from them.

And then there are the people that don’t give AF, or just have no filter whatsoever. Sure, a lot of these questions are hilarious, but if someone actually asked you any of these 21 questions, you’d be awkward in a heartbeat.

But if you’re actually looking to make people uncomfortable on purpose (hopefully as a joke) then by all means, try out one of these bad boys. These are pretty hilarious.. until you get caught up trying to answer one IRL.

These are the 21 most uncomfortable questions you can ask someone:






Written by Alex Cogen

Alex is a New Yorker currently living in Austin. She loves cats, grass, and latex but unfortunately is allergic to all 3. She makes mom and dad jokes more than she cares to admit (jk she'll admit it loud and proud). She isn't as funny as she thinks she is. She is the founder of