Ten Interesting Questions to Ask a Guy Who May Be Shy

interesting questions to ask a guy
Are you wondering about interesting questions to ask a guy who may be shy?  Maybe there is a hottie in your life who you would like to know better or date.  It can be super challenging to interact with someone who is in the hottie zone and not know what to say or what to ask to help him open up and forge a bond.

You may feel like there are missed opportunities for connection, times when you could have opened things up between you that come and go.  This challenging process can even happen when you are first messaging a guy on a dating app, as well as IRL.   It is soooo very frustrating, I know!

So I have prepared ten great tips and questions designed to help a guy open up and start a real, heartfelt conversation with you.  Which can lead to a great friendship, a caring bond, a soulmate relationship and all kinds of wonderful outcomes!

Interesting Questions to Ask a Guy: Tip #1

If you see a hottie on a dating site or app, look at what he says he loves in his profile, validate his interest and ask for more info about it. You will tap into his passion and  he will respond as this is probably something he LOVES to talk about!  So for example, if he says he loves hiking in Waimea Canyon, you could say, “When did you discover Waimea?  It’s awesome!”  Or if he is a Philadelphia Eagles fan, ask him who his favorite player is.

Note, as with all these questions, if he does not respond he is not that interested or available and move on.

Interesting Questions to Ask a Guy: Tip #2

At the beginning of a messaging conversation, you can really open things up by throwing out three questions — two real ones and one funny one to lighten things up. One question is ok – but three, ending with a fun one really gets the conversation more interesting and memorable.  Something like, “Hey Joe I’m intrigued. I’d love to know a bit more about you! For example, where did you grow up? What kind of work do you do? And, most importantly, what’s your ultimate guilty pleasure/ favorite candy/ favorite movie of all time/secret talent/most spontaneous thing you’ve ever done?

Interesting Questions to Ask a Guy: Tip #3

You can also ask a funny questions like “Do you have a power animal?” or If you had a warning label, what would it say?”  “What’s your secret superpower 😉?”  Or, “What  would you do if you won the lottery”?  This differentiates you from all the other women out there.  It makes you stand out because you come across as much more interesting.  And it can really help a guy who may be shy to open up quicky!

Interesting Questions to Ask a Guy: Tip #4

Mine for more info about his goals You can ask questions like, “What brought you to Match (Tinder)?”  He may answer in a way that allows him to open up about his goals.  And this will tell you a lot!  Is he just looking to have fun?  Or to find a relationship?  If he says he is looking for fun or sends a bare-chested photo indicating he wants a hookup, believe him!  Move on!

Interesting Questions to Ask a Guy: Tip #5

A super starting point in either messaging, a casual encounter, or on a first date is to ask, “Do you like adventure?”  It can open up a whole conversation about the cool trips and crazy experiences you’ve each had, and his response also tells you how likely he is to be compatible with you.  Ideally, you want a partner with a similar level of adventurousness.

A more cautious planner type and a just-go-for-it thrill-seeker will generally have a hard time making it work.  So if you’re the type to jump in the car for some surfing at the beginning of a brewing storm and he prefers to prep and plan all the details for a trip ages in advance, you may not click as naturally as you would with someone who shares your appetite for adventure.

Interesting Questions to Ask a Guy: Tip #6

Once you are on a date, ask him to tell you something neutral about his childhood, such as “What’s one of your favorite childhood memories?” Or, “Did you like growing up in Chicago?” After he answers, you might say, “Oh do your parents still live there?” Share more your positive childhood memories. This opens the door to give you more information and ask a follow-up question about his upbringing, such as “Oh, what are your parents like?” If he does share, you can validate him to encourage him to share more.  Say something like, “That sounds so interesting.”

Interesting Questions to Ask a Guy: Tip #7

So after a few dates with a guy who may be shy, a deep question to ask is  “What was the best and worst part of your childhood? The goal is to tease apart a guy’s past in a way that doesn’t feel nosy. So use a casual tone, and only ask him after sharing something about your own upbringing.  If he answers this question honestly, he will start to feel very close to you!  Learning about how he grew up will also clue you into his earliest template for love relationships. If a person is from a difficult background, that often indicates there is trouble coming down the pike. We’re not saying it’s an automatic deal-breaker if his family life was less than ideal, but it is a sign that you may have to deal with some issues in the future.   Listen carefully to his responses.


Interesting Questions to Ask a Guy: Tip #8

The question, “What are you most grateful for in your life?” can really help a guy who may be shy open up to you! This question will reveal loads about his value system and whether it fits with yours. For example, the guy who says he’s thankful for doing his health is quite different from the one who says he’s glad he snagged a big promotion at work.

Interesting Questions to Ask a Guy: Tip #9

“If you could have anything you wanted, what would your dream life be like?” This is a great question because you want to make sure your visions for the future sync up. Here’s how to get at that in a way that doesn’t feel loaded. Is he a free spirit or career-driven? Family-oriented or a bachelor for the long haul? In fact, all of these questions are key things to know.

Interesting Questions to Ask a Guy: Tip #10

After you have had a few dates, a great question to ask is, “What’s the best and worst part of your last relationship?” You can share something like, “I’ve learned so much about myself in my last relationship,” to get the ball going.  Then ask, What’s the best and worst part of your last relationship? Use his answers to assess self insight, blame, narcissism and whether he has an overall negative belief regarding love.

Here’s what you’re looking for: a guy who is willing to open up to you, and as he does, feels like he could be an authentic, solid, caring friend. If possible, one who has a positive outlook on committed relationships.  And for sure, someone who shows he really is into you.

So the next time you wonder, what are some interesting questions to ask a guy, go for it and give these tips a whirl!

You will learn so much, right off the bat!

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  1. Adam Hancock on December 23, 2020 at 4:59 pm

    As a guy who’s been shy at different stages of my life, I can honestly say that the women who made the attempt to ask questions are the ones I eventually opened up to. And through those relationships – the more meaningful ones in particular – I was able to develop more self confidence and share more about myself more openly.

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