60 Random Questions to Ask a Guy…

By on August 1, 2014

First dates can be nerve-wracking to say the least and awkward silences only make it worse. Fill in the gaps by asking him these random but fun questions that will give you a heads up on his personality and your compatibility!

1. What is your dream job?

An answer to this question will give you an insight to his goals and dreams. If he answers right away and can describe exactly what he wants to do, you know that he has thought about this before. However, if he fumbles and mumbles, you may want to steer clear. Who wants to go further with someone who has no dreams?!

2. What is your biggest pet peeve?

Everyone has something that grinds their gears. It is great to know your date’s biggest pet peeve because, who knows, it may be one of your bad habits. If you like him, you’ll know what not to do. On the other hand, if the date isn’t going well, you’ll know how to scare him off! *evil grin*

3. What is your favorite animal?


People tend to favor things that closely relate to them, so a person’s favorite animal can actually say a lot about their personality. Say for instance your date likes turtles, he may be an introverted soul that prefers to be alone. If he likes lions, he may be very outgoing. If he likes dogs…well, he’s probably awesome.

4. If you could live anywhere in the world, where would it be?

Think about the geographic makeup of your date’s dream home. If it is full of hills and plants, he may be a person who loves nature and silence. If it is full of sandy beaches and fun amenities, he may be a party animal!

5. What is your favorite hairstyle on a woman?


Even though  your hair may be your  pride and joy, men aren’t always too concerned about it. If your date is very descriptive when answering this question he is either very turned on by this style, or he has a “type”. If your date doesn’t have a preference, that’s great considering women often get bored and change their hairstyle.

6.    Who is your celebrity crush?

Get to know your date’s ideal woman and why he likes her. There is a thin line between a crush and an obsession though, so make sure he’s not into her in a creepy stalker kind of way. If your date claims not to have a celebrity crush, it may be a sign that he isn’t into celebrities, which can be great depending on your preferences.

7.  What is your opinion on a bromance?

Sometimes a guy’s relationship with his friends can be what ends a relationship. On one hand, you don’t want a loner who doesn’t have any friends. On the other, you don’t want someone who values his “bros” more than he does his girlfriend. The answer to this question can give you a real heads up about your possible future.

8. If you could have a closet full of any designer, who would it be?

Get an idea of your date’s style. If he knows and chooses a high end designer, he may be really into his looks. This may also mean that he takes longer than you to get ready for a date. If he chooses a simple designer or brand (or doesn’t pick one at all), he may be a “get up and go” type of guy who doesn’t care about being the next GQ cover model.

9. What is your favorite type of workout?


Find out what his preferred workout style is. If he likes yoga, it is smart to conclude he lives a holistic life. Those who practice cross fit or weight lifting may take a more “manly” approach to life. If he doesn’t workout at all, well, that could be a serious concern.

10. What is your favorite song?

This is a great way to determine your compatibility. Figure out what genre of music your date likes best and  if you haven’t heard his favorite song, ask him to play it and listen closely to the lyrics. It’s a great excuse to get closer and learn something more about him.

11. What would you do with one million dollars?

We’ve all thought about this one at some point or the other and it would be fun to know what someone you’ve just met would do with that kind of money. If he talks about spending it on material things, he’s probably shallow. Honest but shallow. If he talks about investing it or giving back to the community, he’s a catch!

12. Would you rather have money, or love?


Of course love would be the sweetest answer, but wouldn’t you prefer honesty? If the answer is money, don’t be so quick to judge. Ask him why and listen to his justification. After all, money does make the world go round. Or is that hope?

13. How do you want people to remember you when you are gone?

A legacy is one of the reasons people work hard (well, besides money). The way a person wants to be remembered speaks volumes about his morals and outlook on life.

14. Are you a family man?


Find out how close (or not) he is to his family. Ask about cool family traditions and share yours as well. If your date has any children, this is probably when he would (or should) tell you.

15.  What is your worst habit?

Watch out, his worst habit could be your pet peeve! If you can get through this one without discovering a deal breaker (provided he’s being honest of course), you could possibly be looking at something more than a casual date.

16. What is the most extreme thing you have ever done?

If your date is outgoing and adventurous, his answer will consist of something that is actually extreme (bungee jumping, skydiving etc.). If his answer is something that isn’t so extreme in your opinion, he may be a cautious guy. That doesn’t mean he’s boring though. Safe is sexy in its own way.

17.  What is your favorite day of the week?

Monday can mean your date loves the idea of a fresh start. If he happens to choose the weekend, ask him why. Maybe he loves to party or maybe he just wants to unwind at home with a book. Either way, this question will give you a better idea of how compatible the two of you are.

18. If you could be best friends with someone (dead or alive) who would it be?

See what type of person your date admires. If it is an influential person from history, this may mean he is an intellectual. If he likes to have fun, he may choose a celebrity. Irrespective of who he picks, you’ll get a peek into what kind of friends he seeks in life.

19. What is your biggest wish?


Most people wish for something they don’t have but want the most. It could be something as simple as getting his dream car or something totally crazy. Either way, it would be fun to know what his secret desires are.

20. What is your favorite book?

Personally, I can’t imagine being with someone who doesn’t read. If you’re like me, this is a great way to find out what his favorite book genres and authors are. It could even lead to a stimulating discussion about your respective favorites.

21. Do you have any regrets?

Learn about your date’s worst mistakes. Maybe you’ll have a laugh or two talking about embarrassing incidents from his past or maybe he’ll tell you he has none because he’s the kind of person who likes to live one day at a time and focus on the present, which can be a huge plus!

22.  Do you favor science or religion?

This question will let you know where your date’s faith lies. Knowing his beliefs is important when determining compatibility, especially if your own beliefs are extreme.

23. What is your favorite potato chip flavor?

To be honest, there is no “bad” flavor when it comes to potato chips (how could there be?!) but it’s a great question to keep things light and fun. I bet he hasn’t been asked this one before.

24.  If you could change one thing about yourself, what would it be?


If he answers this question, you may be dealing with someone who isn’t afraid to admit his faults. A guy who feels that he has no flaws may be conceited and could only be looking into your eyes to see his reflection. Run away as fast as you can!

25. What would you do in a zombie apocalypse situation?

These kind of questions are always fun because it gives you a peek into what his mind works like. The quirkier his escape plan, the better. Of course this would be a good time to promise that you wouldn’t eat each other’s brains if either of you’ll turned.

26. Are you a good dancer?

Men who can dance are such a turn-on! If he claims he can dance, challenge him to a dance-off! It would be a fantastic way to share a few laughs and connect.

27.  If you could walk around with a theme song playing in the background, what would yours be?

A theme song would describe your date in a nutshell (or the person he wants to be). Let’s hope he picks something fun and upbeat and not something like “Creep” by Radiohead.

28. Have you ever tried online dating?

A guy who has tried online dating may be afraid to admit it but it says that he still believes in love. Besides in this day and age, who hasn’t tried online dating? Make it fun by sharing a few of your horror online dating experiences.

29. What is your favorite childhood memory?

The type of childhood your date has experienced may define what type of parent he will be. If he has great memories,  he may be excited to have children, if they weren’t so great, he may have a few things to deal with.

30. What is your biggest turnoff?

If you like your date, you want to know what types of things turn him off . You know how you feel about your deal breakers, so pay attention to his!

31. Who is your biggest inspiration?

The person who inspires him is a direct reflection of the man he wants to be. Analyze his choice to figure out what kind of person he is working to become.

32. Tell me about your worst date ever.

His answer will reveal his like and dislikes. It will also give you a sneak peek into how he handles certain situations. Did he leave her to pay the tab, or did he take her home and never call again? This is once again a great opportunity to share a few laughs.

33.  If your food is bad at a restaurant, would you say something?

An assertive guy would speak up and let the staff know BUT without being a jerk about it. Being an ass to your server is a total no-no and a huge red signal! If on the other hand, he doesn’t choose to say anything he could be a pushover.

34. Can you cook?


Aren’t men who cook insanely hot?! If he says yes, you could be coy and say “Maybe you could whip me up something sometime”. If not, you could go with “Maybe we should try cooking something together someday”. Either way, this is a great way to leave things open ended for a possible future date.

35. What is your favorite sport?

This question will reveal your date’s hobbies. You might learn that he likes to actually play sports instead of just watching it on television. Or maybe you support rival teams when it comes to football, in which case you could always have a playful argument about which team is better.

36. UFC or WWE?

A guy who likes WWE may like things that are more dramatic, or full of entertainment. If he favors UFC, he may like more manly things without the extra bells and whistles.

37.  What is your favorite website?

Find out if your date is a social media junkie, or is he one of those rare humans who realize the internet is much bigger than Facebook, Twitter and Instagram.

38. How often do you look at your phone every day?

Dating someone with a phone addiction sucks! When you’re out on the town you don’t want someone who is easily distracted by their phone. On the other hand, if he is a man of business, you may not have a choice.

39. Which cartoon character/animal do you think I resemble most?

Here’s another fun question that will get the giggles going. Remember, don’t be offended by his answers. It’s just meant to be lighthearted fun.

40. Describe your life using one word


Now, this is a hard one so tell him to take his time and choose a word carefully. If he picks a positive word, that means he loves his life and doesn’t regret much. If however he picks something negative, you may want to find out more.

41. What is your dream car?

If a guy likes old school cars, he may be a guy with classic taste. If a guy chooses something newer, maybe something sporty, he may be more modern and adventurous.

42.  If you could be any cartoon character, who would it be?

Find out what type of cartoon your date most identifies with. It will say a lot about his sense of humor. If your guy chooses a villain, he may be a bad boy (hopefully with a good heart!)

43.  If you were ice cream, what flavor would you be?

Mmm ice-cream! If he picks something simple like vanilla or chocolate, he’s probably a guy of simple tastes. If he picks something like green tea or carrot mango, you know you’ve got a crazy one on your hands.

44. Do you own a pet?

If he answers no, ask him what his thoughts on owning one are. Men who are kind to animals are downright HOT!

45. What is your favorite magazine?

A guy’s favorite magazine will give you a closer look at his hobbies, likes, and dislikes.

46.  What language would you like to learn?

Does he pick something romantic like French, something more assertive sounding like German or something downright challenging like Japanese?

47.  What is your favorite snack?


Get an idea of his likes and dislikes when it comes to food. Pay close attention, you may have to cook for him someday!

48.  Describe the perfect woman.

When your date answers this question, try not to compare his idea of perfection to yourself. Afterall, no one is perfect! This question is only to give you an idea of what traits are important to him.

49. What super power would you love to have and why?

Does he choose invisibility so he can be “cheeky” whenever he feels like it? Does he choose the ability to fly? Does he choose teleportation or maybe a little time travel?

50.  You find a valuable item while walking down the street, do you turn it in?

Test your date’s honesty with this question. Most people would keep their findings but if he says he would turn it in, don’t automatically think he isn’t being truthful. Dig deeper and find out why.

51.  If you were gay, who would be your celebrity boyfriend?

Some guys may try and bail out after this question because it is one that separates the men from the boys. If your date can answer this question without getting offended he is very secure with himself. On the other hand if he gets defensive or worse, starts bashing gays, it may reflect his honest views on gay rights and let’s face it, discrimination is never sexy!

52.  Tell me your favorite joke

What a fun way to get the inside scoop on the type of humor your date is into and share a few laughs at the same time. If he continues with other jokes, you may have a clown on your hands. Let’s hope he’s not the kind of guy who’s into toilet humor. Eek!

53. Coffee or tea?

Figure out your date’s morning poison. Maybe you could surprise him with his favorite caffeinated beverage someday. Aww!

54. What is your greatest talent?

Find out if your date has any unique talents. A funny guy might come back with a silly response like curling his tongue or doing a wicked cartwheel. This may also be a great opportunity for you to show off your own talents.

55. If I took you on a karaoke date, would you perform?

A guy who is secure with himself will get on stage and break out his best performance. You know he’ll always be fun and spontaneous as opposed to someone who is worried about being judged.

56.  Have you ever been banned from somewhere public?

If you like bad boys, this is the way to find out if your date makes the cut. If he has been banned from a bar or club, it is safe to conclude he was involved in a confrontation. Make a run for it if he admits to being banned from a retail store though.  No one likes a thief!

57.  What do you think your worst physical flaw is?


Confidence is sexy, but cockiness is a turn off. If your date is a douche, he probably thinks he is a Grecian God.  At the same time, be wary if he has a list full of insecurities because that might mean he’s the jealous type who will make your life miserable.

58. Have you ever cried at a movie?

Being able to show emotion without hesitation can be a great quality in a guy. Most men will probably not admit to this one even if it has happened, so your date deserves brownies points if he says yes.

59. Are you a morning person or a night person?

If you’re the kind who’d rather stay up late like an owl and he’s the “Rise and shine at 6 am” sorts, you may clash when it comes to picking activities to do together. It’s not a deal-breaker though, as long as you’re both willing to compromise every now and then.

60. How tall are you?

Most guys secretly want to be taller so they may add a few inches to impress you. If he is clearly 5’10 but says he’s six feet tall, you’ll probably be asked on a second date. Whee!

There you have it ladies, 60 questions to make your date fun. Remember not to bombard him with all 60 though, not unless you want him to run away.

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