25 Revealing Questions to Get to Know a Guy You Are Interested In

25 Revealing Questions to Get to Know a Guy You Are Interested In

questions to get to know a guy


Brett Larabie

Asking specific questions to get to know a guy is a great way of determining whether or not they are relationship material. It’s my secret weapon.

The best way to learn more about a guy? Asking the right questions to get to know a guy is the most straightforward way to get there. And I have just the way to do it.

Okay, so admittedly this is something I did when I was 16, and I still do it because I think it is fantastic. We played “21 Questions” which ended up being anywhere from 10-60 questions. Basically, you just ask each other questions until one of you tire of it, or you fall asleep.

It’s great. You get to know the guy, and they get to know you. You either bond on an intimate level, or you discover this guy is a sociopath that doesn’t like puppies. Could go either way.

25 questions to get to know a guy you are interested in

Buckle your seatbelts, ladies! These questions will dig deep into this dude’s emotions, and future plans. Not intended for younger audiences. Just kidding, I don’t care, I’m not your mom. Look all you want, kids.

#1 Where do you see yourself in five years? This is a great question because it is relatively soon, but not too far. You will find out if he is ambitious and motivated in his career. Personally, this matters a lot. I’m incredibly motivated by my career success, so I need someone that also values this in their lives.

#2 What about 10 years? This question is a little bit more intense, because depending on how old they are at the time, this means they will be a real adult, doing adult things. If you are even asking, it means you are thinking long-term with this fella. Proceed with caution.

#3 What is your biggest accomplishment? It tells you about how motivated they are, and WHAT motivates them in life.

#4 What is your favorite childhood memory? This is one of those questions to get to know a guy that gives you some insight into what their childhood was like. Without digging for answers, you could potentially learn if they had a fantastic childhood, or if it was rough. This allows them to give up as much or as little as they choose.

#5 Are you closer with your mom or your dad? It says a lot about someone once you know whether they are closer with their mom or dad. If they are closer with their mom, they could be more sensitive and respectful of women. If they are closer to their dad, they could be more masculine and have more difficulty discussing their emotions. Keyword though, “could.”

#6 What is your biggest fear? This could be a funny answer, like mice, or a deep answer, like being forgotten.

#7 What is one thing that you would never want your parents to know? Again, this could be something funny, like they had sex in their bed in high school, or it could be that they were addicted to cocaine. Could go either way at this point.

#8 Describe your dream life. This is literally the perfect question because you can hear how they envision their future, and you get to decide if you could imagine yourself sharing that life with them or not.

#9 If money wasn’t an issue, where would you travel and why? I just really like talking about traveling, so I adore this question.

#10 What is the stupidest thing you have ever done? This one is just fun.

#11 Do you have any regrets in life? Their answer could be “I have no regrets in life, because everything happens for a reason” which I would love, or they could tell you some deep, personal things.

#12 Share your first kiss story. Just embarrassing, awful, and hilarious.

#13 Share your first “time” story. Well, you might get a surprise here. One time I asked this question and the response I got was a red face and avoidance of eye contact. He hadn’t had it yet, and I personally thought that was adorable. #14 What would you say is your biggest turn-on about a woman? Does he describe something about you? SCORE.

#15 Biggest turn-off? Again, does he describe something about you? Okay, maybe not a score this time.

#16 What is the hardest thing, mentally you have ever had to go through? He might describe the death of a family member or his best friend… Just be prepared here, because it could get very emotional. You might be opening up a fresh wound. Proceed cautiously.

#17 Describe your perfect partner. He is basically going to hand you everything he is looking for in a partner in a pretty pink box with a bow on it. Does he describe you? Perfecto.

#18 What is your ideal first date? This question gives you insight into his romantic side. Also, this will tell you if he is a down-to-earth guy that just wants to go to the beach or order pizza and watch a movie. OR if he is extravagant and wants to take you out to a nice dinner with candlelight and such.

#19 If someone gave you a million dollars right now, what would you do with it? Does he give some to charity? PLEASE TELL ME HE GIVES SOME TO CHARITY. Ah, it’s just so cliché. I adore it.

#20 What’s your guilty pleasure? I don’t know, guys, I really like watching Dr. Phil and eating Ben N Jerry’s… But that’s just me.

#21 How do you imagine your future family? Does he want children? Does he want to be married? Does he want to have family dinners every night?

#22 Who is your role model? Knowing who he models his behavior after is super important. This will shape the relationship that you might possibly be entering into.

#23 How would you describe “love”? Maybe he has never actually experienced love. Maybe you’ll be his first. Maybe his idea of love is a very superficial, shallow definition. You will learn it all with these questions to get to know a guy.

#24 What is one thing that you have learned about yourself from past relationships? I’m a firm believer in the fact that every relationship teaches us SOMETHING. If he hasn’t learned anything from his past relationships, then perhaps he lacks personal insight, i.e., he does nothing wrong.

#25 Are you a morning person, or a night person? This is just an interesting question because perhaps you align in this sense. Both morning people? You can wake up and have breakfast together.

Now that you have a lengthy list of questions to get to know a guy, you can test them out on that new relationship—or even one you are already in! It’s always fun to get to know somebody better.


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