15 Questions to Ask a Guy That You Like So You Can Understand Him Better


From open ended questions to the simple questions that could be answered with a simple yes or no, we’ve got 15 first date questions that will help keep the conversation rolling!

Some of these questions are simple, and some of them are intended to simply get to know him.

#1 Where Were You Born?

If he is from out of town, you could ask him when he moved here, what he remembers about his hometown, what his neighborhood was like, etc.

#2 Who Do You Admire Most?

This is a good indication of what is important to him. For example, if he says Mother Theresa, then you can bet he’s got a good heart.

#3 Do You Like Musicals?

If he says yes, you could ask him what musicals he’s seen, what theaters he’s visited and so forth.

#4 Do You Like Museums?

I know a lot of men who are huge history buffs!

#5 What is Your Favorite Kind of Art?

Art is such a broad subject, this will surely lead to some interesting conversations. If you are familiar with the style he mentions, you can talk about your favorite pieces, the artists, and so forth.

#6 Where do You Like to Eat?

Easy, simple, and everybody eats so you can’t lose.

#7 Can You Cook?

If he says yes, you could suggest a second date where he cooks for you. If he says no, you could offer to cook for him. It’s a win-win!

#8 Do You Like to Work on Cars?

If yes, he’ll talk about cars for the next hour.

#9 Do You Have Any Hobbies?

Most people have a hobby, even a failed attempt at a hobby. Who knows, you may even have a shared interest in kite flying or knitting scarves for kittens. You never know until you ask!

#10 Do You Ever go to Carnivals?

Not relative if you met at a carnival or you’re there with him now.

#11 What is Your Favorite Carnival Ride?

Some people may not even like carnival rides. If he does happen to like a ride (and you are actually at the carnival), you could suggest that you ride it together.

#12 What is Your Favorite Carnival Food?

He’ll probably say cotton candy, but extra points if he says Dippin Dots.

#13 Do You Like Concerts?

Believe it or not, some people don’t.

#14 Do You Like Rock or Country Music?

Hopefully, he likes the same type of music you do. If not, perhaps you could ask him to describe the music—or better yet if he has his phone on him and he offers to play a few songs that give you an idea of the genre.

#15 Who is Your Favorite Musician?

Again, hopefully, he doesn’t like some obscure bands that you’ve never heard of. Of course, if he has, maybe he will introduce you to someone new and you can bond over the awesomeness of this new band that he’s introduced you to.