Ask A Guy You Like These 20 Cute, Amazing Questions

Ask A Guy You Like These 20 Cute, Amazing Questions

Have you ever met a guy you really like but feel clueless about what on earth you should talk to him about? Especially if you’re shy, when you meet a guy you like and don’t know what to talk to him about it can be absolutely horrible .

Or maybe you aren’t even shy, but whenever you actually like a guy, you all of a sudden feel shy, as if you don’t know what to say!

When you’re getting to know a guy you like for the first time, you want to have some interesting questions to ask him– so that you can learn more about him and he can learn more about you.

Plus – when you ask him the right questions, you’ll find out pretty quickly whether he’s someone you should really be letting yourself like, or whether he’s not the right guy for you .

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out if he likes you…

So with that in mind, here are 20 amazing, cute questions to ask that one guy:

1. What are your hobbies that you love the most?

Asking him this question is a great idea because you’ll be able to find out if you’ve got any passions in common with him that you can share and do together. Plus, you’ll find out what he really loves.

2. In your opinion, at what point do a guy and a girl become “intimate”?

This thought provoking and dare I say intimate question gets your guy immediately thinking about whether he’s intimate with you – and also gets him to reveal how he thinks about romance and intimacy (1).

3. What’s the first thing you notice when you meet a girl ?

This lets you know where his head is at when it comes to women – and what type of guy he is (2).

4. What’s the wildest, craziest, most insane thing you’ve ever done?

This lets him brag about the crazy stuff he’s done without actually having to brag about it, plus you get to see what happened in his past to make him who he is. Plus, you get to see how crazy he really can be.

5. What’s your favorite romantic thing to do on a date?

Sometimes, there’s nothing more different than a guy’s and a girl’s perception of romance (3). If he’s all about staying in and watching movies together, while you’re more of a go out and have a really nice dinner sort of gal, maybe it’s not meant to work out between you.

6. What was the scariest thing that ever happened to you?

This question gives you a glimpse of what your guy is really afraid of, and tells you more of the backstory behind why he is the person he is.

7. Who was the first girl you ever had a crush on?

You might make him blush – and you’ll definitely break the ice. This is just a cute question to ask him to get him to reveal more about himself.

8. Out of anybody, real or fictional, who’s your biggest hero?

This will reveal what a guy’s values are – what he cares about, what he thinks is right, and what principles he follows. Plus, he gets to talk about himself.

9. Want to hang out together more often?

This is a subtle way of letting him know that you’re interested – and that you want to spend more time with him.

10. Pop quiz: want to cuddle with me right now?

OK – on the cuteness scale, this is about a 10 (unless he says no). But if he says yes – then jackpot!

11. What’s your favorite type of food?

You find out more about his preferences – so you know what to surprise him with if you ever get him food! Plus, you know where to suggest on a date.

12. Do you have a favorite type of car?

A lot of guys are gear heads who love cars… but some aren’t. If he isn’t – no harm done. But if he is, he’ll love the opportunity to talk about something he’s truly passionate about.

13. Has a movie ever made you cry?

Most guys will usually say no to this – but if he’s more comfortable with his manliness then there’s a chance he admits that it’s true! (Fun fact – pretty much 100% of people have cried at a movie).

14. What’s the thing in your life that you’re most proud of?

This is another question that gives your guy a chance to talk about something that’s really important to him – something he considers a core part of his being. It lets you know what kind of person he is, and what he’s accomplished in his life.

15. What do you like to do with your family, and what are they like?

This lets him know you care about the people that he loves, and it gives you a good idea of how he treats his family, how they treat him, and what he thinks a family should be like.

16. Pretend we’re going out – how would we celebrate our 1 year anniversary?

Not only does this let you know whether he’s a romantic or not – it also gets him thinking about what it would be like to date you, and what it would be like to have been in a relationship with you for a year.

17. What’s your favorite sport?

The best part about this question is that guys will either answer which sport they love to play, or which sport they love to watch – and that tells you a lot about them. Either they like to sit on the couch and watch sports, or they like to get on the field and play them.

18. ok – you can go anywhere in the world… where is it and why?

This gives you a good sense of his wish list – where he would want to live, what kind of weather he likes, and what kind of culture he’s looking for… which is all pretty crucial information!

19. What’s your all-time favorite movie?

This will tell you a lot about what his interests are and where his sensibilities lie. If he’s all about action movies while you like quiet dramas, you’re probably not going to agree at the box office very often.

20. What’s something in this world that always makes you smile?

The answer to this question tells you a lot about what his personality is like and who he is. It also lets you know what his sense of humor is attuned to and what he does and doesn’t find funny. Plus, it will probably make him smile!

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out if he likes you…

Take The Quiz: Does He Like You?

In summary…

Cute Questions To Ask A Guy

  1. What are your hobbies that you love the most?
  2. In your opinion, at what point do a guy and a girl become “intimate”?
  3. What’s the first thing you notice when you meet a girl?
  4. What’s the wildest, craziest, most insane thing you’ve ever done?
  5. What’s your favorite romantic thing to do on a date?
  6. What was the scariest thing that ever happened to you?
  7. Who was the first girl you ever had a crush on?
  8. Out of anybody, real or fictional, who’s your biggest hero?
  9. Want to hang out together more often?
  10. Pop quiz: want to cuddle with me right now?
  11. What’s your favorite type of food?
  12. Do you have a favorite type of car?
  13. Has a movie ever made you cry?
  14. What’s the thing in your life that you’re most proud of?
  15. What do you like to do with your family, and what are they like?
  16. Pretend we’re going out – how would we celebrate our 1 year anniversary?
  17. What’s your favorite sport?
  18. ok – you can go anywhere in the world… where is it and why?
  19. What’s your all-time favorite movie?
  20. What’s something in this world that always makes you smile?

questions to ask a guy

34 comments… add one
  • kristen March 24, 2017, 8:07 am

    i like the 3rd question ..!!

  • Anastasia Lou February 5, 2017, 4:58 am

    I’ve try it before.But I’m kinda an innocent girl!he kept asked me to cuddle him all the time when I ask him that (10) question!

  • Kumar Abhishek November 17, 2016, 12:46 pm

    Another good one is, if you could change something you did in the past 24 hours, what would it be? This only worked cause I was with my crush all day yesterday, but he said the one thing he would change is that he would have kissed me.

  • Jack Evans August 4, 2016, 8:56 pm

    haha I asked these questions to a girl and she stopped talking to me

  • Lauren Meza January 23, 2016, 7:59 am

    I really like movies so I would probably ask #19 first.

  • Christopher Hall January 22, 2016, 7:10 am

    There is no doubt that men like to brag about things they did. I can remember a story that i go back to everytime I am asked things like this. Never fails, always gets a gasp :)

  • Kelsey Patterson October 7, 2015, 11:34 am

    I really like paranormal stuff, so getting to know a person by asking if anything scary has ever happened to them is perfect for me.

    • Paul Wallace January 23, 2016, 8:10 am

      Awesome, I am also into ghost and things like that. It is really hard to find a girl that is interested in the paranormal to the point they can hold a conversation.

  • Candace Myers October 6, 2015, 1:35 pm

    I always try to be cute. My last b/f was such a dick and hated it that I felt trapped and had to get away from that relationship. I am glad that I did, because the guy that I am with now, is much nicer!

  • Marilyn Pennington October 6, 2015, 12:06 pm

    I like to ask the car question. You can really learn a lot from a guy when he is willing to share things like that with you.

    • Carrie Morales October 7, 2015, 11:51 am

      I agree. Where I am from, asking about cars will really narrow down the selection.

  • Mary Johnson October 2, 2015, 10:36 am

    I like asking about the first g/f or crush. Most of the time it is a celebrity LOL.

  • Lucille Bryant October 1, 2015, 9:39 pm

    Being cute like this would be so nice for my guy. I am going to ask a few of these questions tonight.

  • Lisa Rider October 1, 2015, 9:30 pm

    These are awesome questions that would be cool for a first date. You could get to really know a person if you make it through a couple of these.

  • Patricia Hamby October 1, 2015, 9:10 pm

    Movies have made me cry before. The weird thing is that the same movies will not have that effect on me if I am with other people. What does that mean?

  • Janet Young September 29, 2015, 9:13 pm

    All very good questions and perfect for that first date or anytime you meet a stranger on the bus.

  • Sherry Mumford September 28, 2015, 9:14 pm

    I have found that asking about family can be a tough subject, so I would advice against that.

    • Ethel Kelley October 1, 2015, 9:19 pm

      LOL. I agree. Sometimes you just never know if it was a good childhood or something they are trying to forget.

  • Irene Rapel September 27, 2015, 11:15 am

    Great questions. My g/f’s and I were talking about things like this last time we met up and I wish I had seen this list before that. Some of these are very good!

  • Donna Pepper September 27, 2015, 11:05 am

    These are all great questions. Thank you for sharing them.

    • Robin Sims September 29, 2015, 9:22 pm

      I thought the same thing. A great way to get to know somebody and maybe even pass along the fact that you might be interested.

  • Mary Craft September 26, 2015, 9:16 am

    I like these questions. They are well rounded and should give you a nice glimpse into the person that is your man!

  • Melanie Woods September 25, 2015, 8:54 am

    I like this. The one thing I see as a possible issue is the fact that he might not think they are “cute”. Then what?

    • Jean Costello January 22, 2016, 7:22 am

      That is true. There are some men that are more annoyed with things like this, I think we have all been down that path.

  • Robert Warren September 25, 2015, 8:41 am

    I have been asked by a date what the first thing about her I noticed. After thinking about what NOT to say for a minute, I answered and I think she was surprised and happy :)

    • Stefania Moody October 2, 2015, 10:46 am

      I bet you were a little scared to even open your mouth huh? :)

  • Anne Gonzalez September 24, 2015, 8:48 am

    I was on a first, blind date one time and a few of these were being asked by me. It is a great way to keep the conversation flowing and the interest in the date on the positive note.

  • Veronica Nichols September 24, 2015, 8:38 am

    I think asking the hero question is a great way to learn about someone. Depending on the answer, you can really tell what type of person they might be.

    • Sandra Michaels September 26, 2015, 9:26 am

      That is right. I feel this would be perfect for a “blind” date, don’t you think?

  • Jennifer Boles September 22, 2015, 1:51 pm

    It would be interesting what kind of responses you get to “have you ever cried during a movie” LOL. All the guys I know are too tough for that.

  • Elise Burch September 22, 2015, 12:32 pm

    I like to ask questions about what type of “romantic” date they like. It kind of opens things up for the past without asking about the past directly.

  • Alison Jiminez September 18, 2015, 2:24 pm

    Guys that I hang around with would not see the cuteness in these questions. They are all the super jock football type and this type of thing would go right over their heads!

    • Cynthia Worthen September 28, 2015, 9:23 pm

      Guess it is time to move along and find a new “group” of guys to hang with!

  • Lynn Martin September 18, 2015, 2:00 pm

    I like the #2 question. That is one that is likely to have a different answer for each person that you might ask.

Leave a Comment