55 Interesting Questions to Ask a Guy Online

We’ve all been there. You find a profile of a guy you like and you start chatting. But then you run out of things to say and the conversation stalls. Our advice? Have a list of interesting questions to ask a guy in your back pocket. 

Do you hate awkward silences? Or need a helping hand to start a conversation with your crush? 

Having some of these questions in reserve is like having conversation insurance. It’s a safety net you can reference to keep the conversation moving naturally. 

So here are 55 interesting questions to ask a guy online, ranging from standard get-to-know-you questions to deep ones about life. 

The Most Interesting Questions to Ask a Guy Online

The Basic Questions

Let’s start with some basics. These questions lay down a steady foundation for the rest of the conversation. 

1.  Where are you from originally?
2.  Where do you live now?
3.  What do you do for a living?
4.  Do you have any siblings?
5.  Do you have any pets?

Get-to-Know-You Questions

Simple but necessary, the following category provides some background information on who your crush actually is. 

1.  Do you speak any foreign languages?
2.  What’s your favorite part about your job?
3.  Do you have any nicknames?
4.  Where’s your favorite place you’ve ever lived?
5.  Do you have any tattoos?

Childhood Questions

A person’s childhood can tell you a lot about them. So when you’re thinking of interesting questions to ask a guy, these are an absolute must.

Maybe he was a total math nerd? Or was he always very driven as a kid? Uncover it all with these questions.

1.  What’s your favorite childhood memory?
2.  What did you want to be when you grew up?
3.  What was your favorite subject in school?
4.  Who had the biggest impact on you as a kid?
5.  Who was your favorite teacher?

Personal Questions

We’re getting into more intimate territory with the following numbers. If the conversation is flowing nicely, ask him these. Understand what makes him tick.

1.  What’s your biggest fear?
2.  Are you close with your family?
3.  What accomplishment are you most proud of?
4.  What do your friends think is your best quality?
5.  What do you think is your best quality?

Dating History Questions

Sharing details about past relationships is a necessary milestone for every couple. But it’s also quite time-sensitive.

Wait until you two feel comfortable chatting before asking him about his romantic past.

1.  When was your last relationship?
2.  Are you usually the dumper, or the dumpee?
3.  What’s your biggest dating pet peeve?
4.  Would you describe yourself as a romantic person?
5.  What’s the most romantic thing you’ve ever done?

Fun Questions

When you’re thinking of interesting questions to ask a guy online, it can be tempting to only include heavy-hitting ones. But sometimes serious questions can get boring.

Remember, you want to date him, not hire him for a job! So don’t be afraid to get silly! Having fun is key to a great relationship.

To lighten the mood, throw a few of these fun questions his way. 

1.  What’s a place you’ve always wanted to travel, but haven’t been yet?
2.  What one thing always makes you laugh?
3.  If you could have one superpower, what would it be?
4.  Have you ever seen a ghost?
5.  What was your first car?

Personality Type Questions

Are you looking for a partner who matches your personality type? Or one who is the yin to your yang?

Discover what kind of this guy he is with these questions.

1.  What’s your zodiac sign?
2.  What’s your Myers-Briggs personality type?
3.  What’s your love language?
4.  What’s your enneagram type?
5.  Which Hogwarts house would you belong to?

“Favorites” Questions

When you’re getting to know someone, uncovering their passions is vital. See what you two have in common with the following numbers.

1.  What’s your favorite cuisine to eat?
2.  If you could only watch three movies for the rest of your life, which ones would you choose?
3.  What’s your favorite book?
4.  What’s your go-to drink order?
5.  What TV show could you watch over and over without getting tired of it?

Deep Questions

Men are like onions. To see what’s inside you have to peel off all their layers. Our deep questions peel back the layers from your crush so you can see who he truly is. 

1.  Do you believe in life after death?
2.  What’s something you could talk about for hours?
3.  If you could go back in time and start over, knowing what you know now, would you do it?
4.  Who or what inspires you?
5.  Do you have a mantra you try and live by?

Flirty Questions

Are you always wondering how to flirt with your crush online? The following numbers promise to spice things up.

1.  What was your first impression of me?
2.  What do you like about talking to me?
3.  What made you want to chat with me?
4.  What compliment would you give me right now?
5.  What would you do if we were having this conversation in person?

“Would You Rather?” Questions

Sure, it may sound juvenile, but this category is always a crowd-pleaser! Make the options as silly or serious and you’d like.

1.  Would you rather read the book, or watch the movie?
2.  Would you rather have the power to fly, or the power to be invisible?
3.  Would you rather always be early, or always be late?
4.  Would you rather be able to see your future or somebody else’s past?
5.  Would you rather have free food for life or free airfare for life?

And there we have it! 

Remember, these questions are here to keep the conversational lulls to a minimum. Not to grill him. So resist the temptation to list off all 55 of these interesting questions to ask a guy online in a row. 

Instead, choose the topic that feels most appropriate and ask your favorite questions from it. Before you know it the conversation will be flowing naturally and you two will be hitting it off. Good luck!

About the author: Elizabeth Entenman

See more articles written by Elizabeth Entenman