40 Personal Questions to Ask a Guy

By on April 13, 2014

Wanting to get a little closer to your potential man? Try out these 40 personal questions to ask a guy and you’ll find out the hysterical, surprising, and event steamiest hidden secrets he’s hiding inside.


1. What is the most embarrassing thing that has ever happened to you?

This questions might be filled with tons of giggles and laughter. But pay close attention to how he answers. If he’s OK with sharing an embarrassing story, it means he’s comfortable with you and probably has a silly personality. However, if he is unsure or avoids telling you an embarrassing story, he is either a closed, shy individual that doesn’t like to make himself look bad or simply isn’t comfortable with telling you.

2. What is the biggest lie you’ve ever told?

Beware of this question! It could be something simple, or it could be something that probably should break off the ties, such as him lying to his ex-girlfriend about cheating or damaging his parents car and not informing them.

3. Would you give up a poker night with the boys to take care of your sick girlfriend?

Hey, some men are the type that will always rather be with the boys than their girlfriend. This is obviously an important matter to find out early on the relationship.

4. What would you do if your ex-girlfriend suddenly wanted to get back together?

If he says he’d get back with her, then it’s obviously time for you to go running in the opposite direction. On the other hand, if he says he would politely reject her then it shows he’s completely over his past relationship and ready to meet someone new. If he says he would mention he’s ‘talking’ to someone (you, of course) then he’s definitely scored extra brownie points!

5. What is the most dangerous thing you’ve ever done?

Some like to play it safe. Does the guy you’re talking to think that ice skating is dangerous, or are you in the midst of an incredibly dramatic and enticing story that is built for an action film? There’s only one way to find out, and that’s with this question!

6. What do you think of open relationships?

It might be every guy’s dream to have multiple girlfriends at one time, but even if he does wish for that he shouldn’t tell you. (Unless you’re also into open relationships, in which case more power to the both of you!)

7. Who is the most important person in your life?

It could be his mom, it could be his dad. Perhaps a grandma, uncle, or best friend? This is a great question and will probably come with an interesting explanation as to why they chose the person they did.

8. What are you attracted to in a woman?

Every man has a different answer to this important, prying question, so obviously it’s a great one to ask! Plus, if you find out he’s into gamers with brown hair and you’re a blonde haired lady who despises video games, you might realize it’s not a match made in heaven after all.

9. Do you have any enemies? Why?

Who knows what this guy did to gain enemies. Egg their cars? Steal their girlfriend? Or maybe he’s so sweet and likeable that he has no enemies. How cool would that be? Ask him this intense question and wait for a very exciting answer!

10. On a scale of 1 to 10, how would you rate me?

Everybody loves to be rated, right? If you’re not afraid of the truth and really want to know how he feels about you, this is a great question to ask.


11. How did your last relationship work out?

Everybody loves to know about peoples past relationships, and it’s definitely an important thing to find out when you’re considering dating someone. You might find out that he’s an overly jealous and controlling man that drove his girlfriend away, or perhaps he was the victim of a cheater.

12. What is your dream tattoo?

You have to seriously like something to get it inked onto your body, so with this particular question you can find out what he’s really interested in or what he loves the most. Maybe it would be a tattoo of his mother’s name, or maybe it would be something silly like his favorite cartoon character.

13. Have you ever cheated on a girlfriend?

If he says yes to this question, we highly recommend you stop talking to this man. Once a cheater, always a cheater! (Although we do appreciate and respect his honest answer).

14. Have you ever had a one night stand?

If he has, it doesn’t always mean he’s a bad person. You know, these things just happen sometimes. But if he’s been a recurring one-night-stander, it may mean he’s only interested in you for one thing.

15. What’s your biggest fantasy?

Let’s just say this question could get very, very…interesting.

16. What is your biggest turn on?

Take note of the answer he gives you- you can use this information later on in the relationship to easily turn him on.

17. What is your biggest turn off?

Just like it’s great knowledge to know what turns him on, it may be even more important to know what turns him off. We suggest avoiding doing anything that turns your man off. (Um, duh!)

18. How many girls have you been with?

Surprisingly you can learn a lot about a man with this simple question. Just beware. men love to lie about this silly question. However, if he says a low number it could mean he’s into more serious relationships while a higher number typically means the man is a player and likes to sleep around.


19. Do you have any phobias?

He could tell you something that will make you laugh, such as a fear of butterflies, or it could be a more in depth question such as fear of death or something else serious.

20. What makes you angry?

If the little things in life tend to send him into an angry rage, then he might not be a good man to enter into a relationship with. On the other hand, it’s good to know what things set him off so you can avoid doing said things. Obviously a very important question that will help you during your time with this guy.

21. What is your deepest, darkest secret?

Here’s a fun one that can either make you laugh or make you scared. Either way, if he’s willing to share his deepest, darkest secret with you, he must feel pretty comfortable with you- and that’s a plus!

22. Have you ever wanted to be a woman?

If he says yes, let’s just hope he has a really good reason for his answer.

23. What is one question you absolutely refuse to answer?

There are some things we just don’t like to discuss or answer. You can find out what your potential mate doesn’t like to answer, simply by asking him this question. Just remember- you won’t be able to find out the answer to the question he refuses to discuss, so take note of this before asking him. It might just drive you nuts!

24. What are you most insecure about?

We all have things that we are insecure about, but is your guy so stuck up that he’s confident in every aspect? Or is he willing to admit that he’s insecure about his nose/eyes/personality/job? Whatever his answer his, reassure him that he has nothing to be insecure about and you love his _____.


25. What does love mean to you?

Everyone has a different answer for this, and it’s definitely an important thing to find out early on the relationship. We just hope he doesn’t respond with one of those, “I don’t believe in love” phrases. We hate those!

26. What are some of the morals you live by?

You can seriously find out a lot about a person by knowing the morals they live by. We guarantee this is a prying, personal question that is unlike any of the others.

27. What is your goal in life?

Another excellent personal question that will help you discover a bit more about his personality, wants, and needs.

28. Do you like the lights on or off?

This is just a fun question that you can save the answer to for later. (Wink wink).

29. Do enjoy one on one outings or do you prefer big groups?

You can discover a lot about a person’s personality with this simple question.


30. What is your favorite body part on a female?

If he says anything other than the breasts or butt, that’s huge brownie points for him. Shows that’s not ALL he thinks about!

31. What is one thing you don’t like about me?

He should say you’re perfect, of course! But in case he doesn’t, just be positive and don’t overreact to his answer.

32. Are you a virgin?

You will probably find out the answer to this with some of the above questions, but if you just want to flat out find out if he’s been busy or not, then ask him this straightforward question.

33. How many times have you been in love?

This is just one of those questions that you should be asking your potential lover. It’s important, as you’ll find out whether he’s quick to fall for someone or if it takes time.

34. Have you ever longed for a woman that was much older than you?

One of his sexual fantasies, perhaps?


35. What is the worst date you’ve ever been on?

Get ready for tons of laughter with this one!

36. What is a deal breaker for you?

Obviously this is something very important to know. If his deal breaker is a girl that doesn’t like football and you absolutely hate football, it clearly won’t be a very long-lasting relationship and you should probably let him know ASAP.

37. Are you religious?

The answer to this could either be really good or really bad, depending on where you stand.

38. What is your strangest habit?

We all have one, right? What’s his? You won’t know until you ask him!

39. Have you ever had a wet dream?

I think every man has had one, right? Well now’s the time to own up to it, dude!

40. Are you financially stable?

Of course we aren’t talking to him for his money (or lack thereof). Find out if your man has a secret stash in his bank account from all his hard work, or if he wants you by his side as he struggles through college trying to reach his dream career.


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