Having a crush on someone is already hard enough. But when you don’t even know what to talk about with your potential boyfriend, the whole situation becomes even more stressful. Try out these 20 questions that will break the ice and help you get to know them better.

1. Are you seeing anyone?

This should always be the first question. If the answer is ‘yes’, then you clearly don’t need to continue with the following questions. Either move on, or take a risk and see if the current relationship fails.

2. What do you look for in a woman?

This question helps you to determine if you two are even compatible. Just remember: if you’re not his type, don’t change yourself just to please him.

3. How long was your longest relationship?

If his longest relationship was only 3 weeks, it may mean that he’s not looking for anything serious. On the other hand, if he’s been involved with someone for several years, it could mean that he’s a romantic man looking for love.

4. What is your worst habit?

An important question because it could potentially be a deal-breaker. For example, if his worst habit is smoking cigarettes and your an avid non-smoker, you might realize he’s not the one for you.

5. Who’s your celebrity crush?

Finding out his celebrity crush can give you an idea on what kind of woman he’s after.

6. What is your favorite television show of all time?

With this question you can find out a bit of his personality. A guy who loves television shows with plenty of action might be a tough guy, while a man obsessed with comedies might have a funny and cute personality.

7. Would you rather have unlimited love or unlimited money?

If he answers ‘money’, you might be dealing with a materialistic man who cares more about goods than his partner. On the other hand, a guy that picks unlimited love shows he is extremely caring and truly looking for his soulmate.

8. Snowboarding or surfing?

Finding out whether he’s a rugged snowboarder who fights against the snow-topped mountain peaks or a relaxed surfer gliding along the waves can really give you an idea about his personality type.

9. What’s your favorite genre of movies?

Another great way to find out more about his personality is to find out what genre of movies he enjoys. As an added bonus you’ll be able to know which movie the two of you can see together on a first date!

10. What’s the most embarrassing thing that’s happened to you?

Not only will this get a good laugh, but you’ll be able to see a different side of him: if he doesn’t share, he may be unconfident or simply mysterious. If he does share, he might be a joker who loves to mess around.

11. What is your weirdest deal-breaker?

Finding out what is an automatic deal-breaker for your potential man is just something you need to know to see your compatibility and also refrain from doing whatever it is his deal-breaker is.

12. What is your idea of a dream date?

With this question you can find out exactly what type of boyfriend he is: a romanticizer or a bore-fest.

13. What do you like about yourself the most?

See how confident he is in his own skin.

14. Does he think you’re cute?

This question might be a bit out there and upfront, but there’s no better way to see if someone is interested in you than to be completely honest. If he says yes, you’re in the running for next girlfriend!

15. Have you ever been in love?

If he says yes, than he will know a thing or two about romance. If he says no, he might be a bit immature when it comes to the love game. But you can change that, of course.

16. What is your biggest fear?

Find out whether he’s a total pansy afraid of butterflies or if his fears are much greater and deeper than anything you’d thought possible.

17. What is your favorite food?

Here you will find out if he is the adventurous type, diving into the realms of hot spices or whether he’s an all American man who enjoys a pizza and a beer.

18. What is your favorite color?

Colors can actually tell a lot about a person. If he chooses a subtle color like green or blue, he may be more relaxed while someone who chooses red may have a hot temper.

19. Why did your last relationship fail?

This particular question may be a bit too personal for some, but if he chooses to answer it can tell you a lot about his dating habits.

20. Is he interested in you?

Another straight-forward question that will let you know right there and then if he’s interested. If you feel like taking a risk and don’t want to wonder about the potential of you two dating, be upfront and ask him if he’s interested.

Image credit: Danique, bilge, thelle548

When getting to know the guy you are interested it, it’s important to have strong, cute and interesting questions to ask him to help the bond between the two of you develop. Asking all the right questions will help you get to know your crush and even help you decide if he is really someone you want to take the next step with. Here are 20 good and cute questions that you can ask the guy you like:

[ Read : 100 Questions to Ask Your Boyfriend ]

Question #1.) What makes you smile?

Why It’s A Good/Cute Question: Asking this to a guy you like let’s him know that you are curious as to what makes him happy. The answer will let you know how to make him smile in the future and helps you get to know him much better.

Question #2.) What’s your favorite movie?

Why It’s A Good/Cute Question: The answer to this question will help you both to discover if you have common interests when it comes to movies and the more you have in common the better!

Question #3.) If there is any place in the world that you could go, where would it be and why?

Why It’s A Good/Cute Question: This is another one of those ‘getting to know him’ type of questions. Maybe you both dream about the same places, who knows?

Question #4.) What is your favorite sport to watch/play?

Why It’s A Good/Cute Question: A lot of guys absolutely love talking about sports and this will get conversation flowing. Hopefully, you can retain some of that knowledge and maybe even get yourself invited over to watch the game! Asking this question also lets your crush know you are interested in his likes and dislikes and want to get to know him better.

Question #5.) If we were dating, how would you celebrate our first one year anniversary?

Why It’s A Good/Cute Question: Asking this benefits you in a way that the answer will tell you if he would do something you like. Answers to questions like these can help you figure out what type of romantic he is and if he cares enough to tell you!

Question #6.) What’s your family like?

Why It’s A Good/Cute Question: He’ll love the fact that you are taking the initiative to get to know the people he loves.

Question #7.) What about yourself do you find the most pride in?

Why It’s A Good/Cute Question: Whether the answer is about his looks, talents or personality, you are engaging him in conversation that implies you want to get to know him and what he takes pride in. Pride is a huge trait in most any guy and definitely something to be aware of.

Question #8.) Have you ever cried at a movie?

Why It’s A Good/Cute Question: Honestly, the answer to this question is usually a no, but if he does answer yes then maybe he has a really cute sensitive spot!

Question #9.) What’s your favorite car?

Why It’s A Good/Cute Question: This is another subject that most guys enjoy discussing. If he’s a car lover, he will adore you for asking and he will enjoy telling you all about what he likes.

Question #10.) What is your favorite food?

Why It’s A Good/Cute Question: The more and more you get to know him, the better a relationship will grow!

Question #11.) What do you notice first when you first meet a girl?

Why It’s A Good/Cute Question: This answer will also give you good insight to what kind of guy your crush is.

Question #12.) What is the craziest thing that you have ever done in your life?

Why It’s A Good/Cute Question: Not only will this give you a glimpse of his past, but it will also let you know how far this guys boundaries are and if you can keep up with them or if you want more excitement than what he is willing to do.

Question #13.) What is your favorite romantic activity?

Why It’s A Good/Cute Question:  A guy has a different view on what is romantic than a girl does. So, be careful about how you take your crushes answer. If he answers, “We would play video games all day and drink Mountain Dew” and that’s not your favorite idea of romance, maybe he’s not a right fit for you. On the other hand, if he at least puts a little bit of effort in and says, “We could have a picnic at the park” or “I would take you shopping” then maybe he is a keeper after all!

Question #14.) What was the scariest moment in your life?

Why It’s A Good/Cute Question: It’s nice to get to know a guy, what he’s afraid of and why.

Question #15.) Who was your first crush?

Why It’s A Good/Cute Question: This question is just a small ice-breakers and may have him blushing or you laughing, but it is a cute question to ask.

Question #16.) Who is your biggest hero?

Why It’s A Good/Cute Question: Asking this question to the guy you are interested in will help you get to know who he looks up to and who he aspires to be like. It is just another ‘get to know him’ type of question that can really warm you up to each other.

Question #17.) Would you like to hang out with me more often?

Why It’s A Good/Cute Question: This lets your crush know you are interested in him and seeing him more often. It is even cuter if he says yes!

Question #18.) What is your definition of intimate?

Why It’s A Good/Cute Question: Asking this question and receiving its answer will give you an idea of how your crush perceives intimacy and romance. The answer can be quite heartwarming and adorable!

Question #19.) Would you cuddle with me?

Why It’s A Good/Cute Question: Oh! The cuteness! Unless he says no, of course, then it is not so cute… But, if he says yes, it is definitely an adorable question to ask.

Question #20.) What are your favorite hobbies?

Why It’s A Good/Cute Question: Maybe when he answers you will discover that you both have a lot of common interests and can even do some of those hobbies together. This will help you to get to know him much better and discover what he truly loves doing.

Whether you want to crack a few smiles, really get to know him or just want to play an amusing game of 20 questions, the questions put together below can truly be hilarious to ask the guy you like! You and your crush will both be smiling by the end of every answer. Here are 20 funny questions for you to ask the guy you like:

Question # 1.) What would you do if you could be invisible for one whole day?

Why It’s Funny: Knowing most men, their answers would somehow probably include them snooping around the fitting rooms of that lingerie store in the mall! Surely, you’ll get a good chuckle out of whatever he answers with.

Question #2.) What’s your favorite joke?

Why It’s Funny: Whether this joke is actually funny or not, watching him trying to put it together and try to make it funnier so that you’ll like it as much as he does- priceless.

Question #3.) If you could be a woman for one day, what would you do in that day’s time?

Why It’s Funny: This one has got to hilarious! Men don’t understand women as well as we’d like and so they are truly fascinated and equally freaked out by women, so imagine what they would do all day…

Question #4.) What is the worst thing that somebody has walked in on you doing?

Why It’s Funny: Obviously it was an embarrassing moment for a reason and usually embarrassing moments are pretty funny!

Question #5.) What is the weirdest nickname people call you?

Why It’s Funny: Whatever he finds weird about the name will probably crack you up because it’ll be silly or embarrassing.

Question #6.) Do you think you’re attractive?

Why It’s Funny: There is almost nothing funnier than watching a guy feel a tiny bit awkward about the question and then try to puff out his chest and talk overly confident about himself.

Question #7.) Can you list three words that describe yourself?

Why It’s Funny: Well, when a guy pulls out three words like, “Sexy”, “Charming”, and “Awesome” you usually get a darn good laugh about it.

Question #8.) What would people hear if they could read your mind?

Why It’s Funny: Not only guys, but usually everyone has some weird and funny thoughts that pass throughout their heads all day long… but, guys are usually way funnier!

Question #9.) What’s your dumbest pet-peeve?

Why It’s Funny: Imagine him saying something like, “When my mom tells me to put my socks away while I’m playing Call Of Duty.” Plenty of guys have really silly pet-peeves that they get super mad about and their reaction may get anyone to chuckle a little bit.

Question #10.) Who is your celebrity crush and why?

Why It’s Funny: This is a funny question to ask because a guy will usually just name off a celebrity or celebrities with the biggest… well, you know!

Question #11.) What are you afraid of the most?

Why It’s Funny: Most dudes don’t like to discuss their fears because they think it makes them look weak. So, to hear a guy actually fumble for a less weak answer is pretty funny. Or, if he is honest and says something funny like, “Kittens” or “Bunnies” you might get a laugh out of it.

Question #12.) What is your biggest turn on?

Why It’s Funny: It is pretty amusing to ask awkward questions to guys and sometimes the answer to this question can be really funny to you!

Question #13.) What is your best talent?

Why It’s Funny: Sometimes, especially is you just met this guy, he might try to over-exaggerate to make himself sound cooler to impress you. So you may hear something like, “I’m totally amazing at driving race cars. I win  first place all the time!” When in reality, he probably just one the soapbox derby in 4th grade and received a blue ribbon.

Question #14.) Would you miss a sports game for me?

Why It’s Funny: Most guys are totally obsessed with sports, whether it be football, soccer, basketball… whatever… When asked he will probably get all flustered or even straight out say probably not. Come on, that’s pretty funny, right?

Question #15.) What was your most awkward sexual moment?

Why It’s Funny: I don’t think this one needs an explanation… if it was sexual and award… it’s probably going to make you laugh.

Question #16.) What was your most embarrassing moment?

Why It’s Funny: Usually, embarrassing moments are pretty funny and even funnier when the person who was embarrassed is explaining the moment.

Question #17.) What would you do if you won the lottery?

Why It’s Funny: Guys have a completely different way of thinking than women and some of the ways that they’d spend all that money… well, it’s ridiculously hilarious.

Question #18.) If you could commit any crime and get away with it, what would it be?

Why It’s Funny: Alright, so this probably isn’t true for just any guys, but sadly, answers like, “Steal the new Madden 25 game” or “Break into Jessica Alba’s house” have been given… Ha!

Question #19.) If you could see the future, what would you hope to see yourself doing in 5 years?

Why It’s Funny: It’s always something else to hear a guy talk about how he sees himself doing in the future… if he can think that far ahead!

Question #20.) What’s your perfect girl like?

Why It’s Funny: I can hear almost any guy going, “Well she’s got to have huge….!”

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