120 Questions to Ask a Guy You Like That Will Blow His Mind

If there’s a guy in your life you want to get to know better, then you’ll have to employ tactics other than small talk and politeness. You need a great conversation starter.

To help you along the way, we’ve come up with a list of questions to ask a guy ranging from flirtatious, deep, personal, and then some.

What do you look for in a girl?

Find out if he’s more into looks or personality. Or perhaps something else entirely!


Do you have any family traditions?

Asking him about family traditions will open up an entire world of conversation topics.


If you fall for someone do you wait to say so until it feels socially appropriate, or do you just spill your guts?

This is also a good question to ask so you know not to overthink your situation with him.


What’s the most trouble you’ve ever gotten in with your parents?

Is he a bad boy or are his parents just strict? This is also another chance to find out more about his family without asking a more straightforward question.


Have you ever done anything illegal?

So, has he ever broken any laws? Maybe he never got in trouble at home because he’s never been caught.


What were you like in school?

Was he the class clown, jock, nerd, or just your average guy? This is your chance to learn more about a side of him you never met.