40 Casual Questions to Deeply Get to Know a Guy You’re Interested In

How can you be sure if you’re suited to someone if you don’t know the small details about them? Learn some questions to get to know a guy and ask away!

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 we have just the way to do it. Memorize some questions and weave them into your conversation seamlessly; it works like a charm!

Okay, so admittedly this is something people do when they’re in their teens. When you’re in school, it’s easy to play “21 Questions” which ends up being anywhere from 10-60 questions!

But you can still ask a guy a few fun questions casually by slipping in a question or two now and then. Basically, you just ask each other questions until one of you tire of it, or you fall asleep while texting each other. [Read: 71 friendly and funny questions to get to know someone better in a happy way]

One of the best things about these questions to get to know a guy is that you can actually get to know the guy, and he can get to know you a lot better as well!

You either bond on an intimate level, or you discover this guy is a sociopath that doesn’t like puppies. Could go either way.

If you don’t like the idea of batting questions back and forth, you could simply be a little sneaky and direct the conversation towards specific things you want to know. It takes practice, but once you master it, it’s a great tactic to have in your dating armory!

[Read: 22 early warning signs of a bad boyfriend you need to leave ASAP]

Wait, don’t you get to know one another slowly over time?

Admittedly, yes, but having a little pre-information is never a bad thing. Why waste your time on someone you know that you’re not going to click with?

By asking some questions to get to know a guy, you can work out whether this is a guy who is worthy of your time and attention, or someone you should pass on.

Getting to know one another over time is a totally different type of familiarity. That’s about making memories together and growing as a new couple.

But by asking these pre-dating questions, you can work out whether you’re suited. Do you have the same values? Does he like animals? What is his favorite color? You know, the important things in life! [Read: How to get to know someone on a date]

Of course, one thing you shouldn’t do is make him feel like you’re interviewing him. That’s not cool or fun.

If you’re going to go down the quick-fire question game, fair enough, fire away, but make sure he knows it’s a game and not a grilling he wasn’t pre-warned about!

The best casual questions to get to know a guy and make him open up to you

Buckle your seatbelts, ladies! These questions will dig deep into this dude’s emotions, and future plans. Not intended for younger audiences. Just kidding, we’re 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.

Generally, this matters a lot, especially if you are career-driven as well. [Read: 50 relationship questions to test your compatibility instantly]

2. What about in ten 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?

This question tells you about how motivated they are, and WHAT motivates them in life. [Read: Stop being a wallflower and talk to the guy you like]

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. Who are you closest to in your family?

It says a lot about someone once you know whether they are closer with their mom, dad, sisters, or brothers, etc.

If they are closer with their mom or female family members, they could be more sensitive and respectful of women. If they are closer to their dad or male family members, they could be more masculine and have more difficulty discussing their emotions. Keyword though, “could.” [Read: Feminine men and 40 signs of a guy who’s more in touch with his softer side]

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. [Read: 20 good questions to ask a guy and find out who he really is]

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?

Everyone really likes talking about traveling, so he will adore this question. It also tells you a lot about a person in terms of the types of landscapes they like, the cultures they’re pulled towards, etc.

Let’s be honest, if they’re a ski and snow kind of guy and you can’t stand anything below 90 degrees, you’re just not a great match! [Read: 9 reasons traveling is a great test of compatibility]

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 you could 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. He may just laugh it off, go into explicit details *in the hope of making you horny!* or you may just find out he’s red-faced because he’s still a virgin! [Read: 28 awkward questions to ask a guy and the weird ones you never should]

14. What would you say is your biggest turn-on about a woman?

Does he describe something about you? SCORE.

15. Your biggest turn-off?

Again, does he describe something about you? Okay, maybe not a score this time. [Read: The biggest dating turn-offs for guys]

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 with this question to get to know a guy. So 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. [Read: Top 50 amazing first date ideas to wow your date]

19. If someone gave you a million dollars right now, what would you do with it?

Does he give some to charity? Does he keep all of it? Spend it all in a week? Ah, this question to ask a guy and get to know him is just so cliché but it still reveals his inner workings!

20. What’s your guilty pleasure?

Porn? Social Media? Dark movies and shows on Netflix? What is it? [Read: 33 guilty pleasures you should keep a secret]

21. How do you imagine your future family?

Does he want children? Can he envisage getting married? Could he imagine 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. Perhaps 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?

Are you a firm believer in the fact that every relationship teaches you 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 to get to know a guy because perhaps you align in this sense. Both morning people? You can wake up and have breakfast together.

26. What is your favorite animal?

Let’s be honest, a guy who loves animals is instantly more attractive than one who doesn’t. Is it a cute dog or a cat? Is he more about reptiles than cuddly animals?

27. What trait do you consider the most important in a partner?

Most people will say honesty or faithfulness but it’s interesting to ask. This is one of the more searching questions to get to know a guy because it tells you what is important to him. He might surprise you. [Read: 20 positive personality traits that can change your life forever]

28. Sex on a first date or not?

A cheeky one but it’s fun to ask! Most guys will say that they don’t want to have sex on a first date but most are lying. If you make it to a date, it gives you a few ideas on whether you want to go there or not!

29. What makes you super angry?

This can give you some very interesting insights into what he can tolerate versus what makes his blood boil. It’s always fun to learn these things and of course, tells you what to avoid!

30. If you could change one trait about yourself, what would you choose?

Nobody is perfect and the fact he can choose a trait tells you that he knows this and he’s working towards self-improvement, in some way at least. If he tells you he’s perfect and wouldn’t change anything, he’s lying. [Read: 33 traits of a good boyfriend you should always look for in a guy]

31. What is your favorite movie of all time?

His favorite movies don’t just reveal how he likes wasting his time, it actually talks about his core values and what makes him who he is. Use this question to get to know his favorite movies, and chances are, the lead male characters are people he associates with or aspires to be.

32. Who is your favorite actor?

Is it an action specialist? A deep and meaningful actor? A comedic genius? This is one of the questions to get to know a guy that will give you a real insight into what he finds entertaining.

33. Do you really like your job?

This is a loaded question and one that could take the conversation further. He may say that he loves his job and tell you why. Or, he may say he hates it or doesn’t enjoy it generally, and what he would like to do. [Read: Love or career? How to make the right choice]

34. If you could relocate and live somewhere else, where would you choose?

This is a little like the travel question, because it tells you about the types of locations he likes. Again, sub-zero temperatures could be a serious red flag for you!

35. What is your go-to song on karaoke night?

He’ll probably tell you he doesn’t do karaoke but that’s just his ego talking. Push a little further and he’ll buckle under the pressure and admit that he likes “I Will Survive” or something just as cheesy!

36. What was your childhood nickname?

Out of all the questions to get to know a guy, this one will make him smile and take him back to his childhood years. Just try not to laugh when he tells you what his mom used to call him! [Read: 50 cute things to call your boyfriend to create intimacy]

37. One pillow or two?

Another cheeky one because it gives you pre-information if things were to get intimate!

38. Ross & Rachel, were they on a break or not?

Even if he wasn’t an avid ‘Friends’ watcher, he is probably going to understand this debate and will probably also have an opinion on it. Does his answer match yours?

39. If you could have dinner with one famous person, who would it be and why?

Will he choose a beautiful actress just because he can, or will he choose a highly intelligent historian so he can pick their brains? Of course, there’s a huge amount of ground between those two examples! [Read: What to look for in a guy – 40 traits that make a man worth dating]

40. Is the glass half full or half empty?

Is he an optimist or a pessimist?

[Read: 60 fun get-to-know-you questions to know your new romantic partner]

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 someone better.