Good questions to ask a guy when you’re stepping into the crazy and exciting world of dating can be very intimidating. You don’t want to be too nosey or pushy, but if you don’t establish some sort of emotional connection right up front, boredom will set in or he’ll just find the next fish in the sea.
Your quest is to see if you’ve got any connection, if there are any deal-breakers, and if your dating intentions match. Maybe he’s looking to date a couple girls and nothing serious and you are hoping to find that guy who wants a committed relationship?
Understanding what to ask and when is vital for successful dating.
On the flip side…
You need to learn what not to say when you are trying to figure out whether this hottie is right for you or not. There aren’t any guarantees but the more you know about what to ask and what to steer clear of when you are on the dating scene, the better.
It’s all about making sure you are having fun but at the same time you need to make progress. This means you’ve got to ask the right questions to find the logical balance that triggers some emotions and trust, and gets the answers you are looking for.
Good Questions To Ask A Guy You Like
1. How many girlfriends have you had in the past year?
This is going to give you great insight as to whether or not this guy is a serial dater or someone that likes to focus on one girl at a time. If the guy says he’s had 5-6 girlfriends in the past year that’s a negative pattern. Stop where you are no matter how charming he is and look elsewhere. This guy is just guaranteed to give the gift of heartache, according to Healthy Living experts.
2. Are your mom and dad still married?
Another top notch question because this gives you a signal about his family life. If he tells you his mom and dad have been happily married for 25 years, that’s a great signal for you. Just means this guy knows two people can commit to each other because he’s lived it and that’s a great place to start.
If on the other hand he tells you that he lived in foster homes all his life and the people that finally adopted him when he was 12 just got divorced, that’s not good news for you. It doesn’t mean he can’t be good boyfriend material, just be wary.
3. Ask him what his passions are?
The way he answers this will tell you lots. If he tells you he really doesn’t get too excited about anything but he does like sleeping in, you’ve likely got a lazy dude on your hands that you just don’t need. Not unless you’re a lazy “dudette” and then you’re a match made in heaven.
If he tells you he loves animals and traveling, and playing sports every chance he gets, in line with you, then he’s worth pursuing.
It’s not that you have to love everything he does, but you should at least have a genuine interest to learn more.
4. Psychology Today says you should ask about his friends.
What’s important to know is if you are going to be entering a relationship with a guy, it will involve his friends. To get him to tell you a little bit about his friends, you can get a better picture of his character and what he likes.
Remember, we are all products of our environment.
5. What sort of hobbies does he have?
If you are a total bookworm and he’s a major jock, and you’ve zero interest in “jock stuff,” then chances are you’re not a match. Relationships are tough and you need at least a few things in common if it’s ever going to work.
6. Are you a morning or night person?
This is really only crucial if you are in the extreme. If you get up at the crack of dawn and literally crash at 4 and he sleeps as long as possible and never gets to bed till 1 or 2 am, then you’ve got an issue. Sounds like even when you do find time to spend together, one of you will surely be sleeping!
Just be sure you are compatible here.
7. Are you close with your family? How big is your family?
Again, this will tell you a lot about him. If he comes from a big loving family, then you’re good to go. If he has a dysfunctional family where his sisters are pregnant and single and living at home, and his mom is an alcoholic. Or he doesn’t know his father, it doesn’t look like he’s had a chance to learn some of those social and familial traits you’re likely searching for.
Probably is best if you steer clear of this guy no matter how cute you think he is.
8. Do you do drugs, smoke, or drink?
This is a really good question to ensure you end up with someone compatible. If smoking is a deal-breaker for you and a guy tells you that he smokes occasionally, you need to stand firm in your decision. Don’t stray from the important qualities you are looking for in a guy.
You can tell him exactly how you feel and leave the ball in his court. Just be true to you.
9. Do you have any dietary restrictions?
Trust me, you can get yourself into trouble if a guy is all anal that he eats only organic food, or follows some other crazy impossible and inflexible diet plan. It’s great you have an eating plan but it turns negative quickly if it alienates you from the rest of the world, according to Women’s Day.
Before you agree to get to know each other any better make sure you ask him his food preferences.
10. Are you religious?
This isn’t usually a problem unless of course it’s in the extreme. For instance, if you are a relaxed Catholic and he’s a practicing Jew; follows all the holidays and does Sabbath every Friday night religiously, you’re into a whole whack of conflict before you even start. I learned through experience that a devout Jew often has a negative perception to start toward anyone that isn’t Jewish. Even if you are Jewish and aren’t keeping up with your studies, the devout Jews will frown upon you.
It is very difficult to coordinate schedules because this religion has all sorts of restrictions. Many you can’t be involved in unless you are naturally Jewish. They frown against conversions and make it very difficult.
Just be sure you make sure you are compatible in the area of religion before you go any further.
11. What type of movies or television shows do you like?
This is another question that will tell you pretty quick if you have any common ground. If you both love adventure movies there will be lots to talk about. And there’s nothing wrong with having a first date at the movies!
12. What’s your favorite restaurant?
An excellent question that opens the door to cuisine. From here you can ask him what his favorite food is. What does he like for breakfast? And maybe what’s the best meal he’s ever had?
All clues to how you can make this guy fall head over heels for you through his stomach!
13. Are you dating anyone else?
It’s important to know whether this guy is a player or if he’s a one woman kinda guy. Not that you should believe everything he says just yet, but it’s a good start to hear him tell you that he isn’t dating anyone else. Do you really want to be sloppy seconds?
If he is dating someone else, just kindly let him know if things change, he can come find you. Gives him something to think about anyway.
14. What was your best drop the mic moment?
I’m sure your guy would like to tell you an awesome story about himself. This will give your guy a chance to shine and get him talking and open up. You will also learn about what kind of things he likes and is into or what he considers important.
15. If you wake up suddenly in the middle of the night, what would be the scariest sound to hear?
This question can reveal what he is potentially afraid of or he could simply make you laugh and turn this question into a joke. Either way, it’s a great question to ask your guy and it surely will get the conversation going. You can also talk about a scary movie you have both seen or talk about the fears you might have in common.
16. Who or what is your nemesis?
Everyone has people or things they dislike or hate. I’m pretty sure your guy has them too. This question is great for getting to know what things annoy him. It reveals a lot about a person. Listen carefully, there may be answers that you might not like or appreciate.
You can also turn this question into silly or funny answers like disliking websites that don’t load fast enough or jars that won’t open. This question doesn’t need to be serious if you are not comfortable with it.
17. What childish things do you still enjoy doing?
We all have silly childhood things that we carry over to our adulthood. I’m sure your guy is no exception. He may not want to admit it but he probably still likes building sand castles or wrestle with siblings. This is a cute question to ask and will likely get you some sweet answers.
18. What movie can you watch over and over again?
Most people have their favorite movies that they don’t get tired of watching. This is a great question to ask so you can learn about his favorite movies and why he likes them. You will also learn what genres and shows he likes watching. This question can be easily expanded upon because you will both end up sharing your favorite TV shows and movies as well the shows you dislike.
19. If you built and designed a tree house, what would it look like and what would be in it?
What kind of a guy doesn’t like a tree house. I’m sure they all secretly would like an impressive get away tree house. You’ll learn about your guy’s fantasy and creativity of a perfect tree house. Either be it with drop down ladders or massive bridges. There is a reason guys wish to build a tree house for their kids. It’s not for the children, it’s for them.
20. What is the most useless thing you know how to do?
This question reveals if your guy has any hidden talents. You may be surprised by his talents. It’s also fun because most likely he can just show you. This is a great way to take the edge off the seriousness of the questions. We all have some silly talents and now is your opportunity to learn about his!
21. What is the highest pressure situation you have experienced and how did you handle it?
This question is somewhat similar to the drop the mic question and this one will give your guy an opportunity to tell you about a story that is important to him. Just be prepared that there will most likely be some embellishment and exaggeration happening when telling his story, even if he doesn’t really mean to. Memory is surely a funny and flawed thing after all!
22. What events made the biggest impact on who you are today?
This is one of my favorite questions to ask a guy. It’s a bit more serious question and it will let you know more about his past, what he considers important and how he views himself. The question is also very useful because there are endless follow up questions you can ask about his answers and events in his life.
23. What’s something you were really stressed about, it turned out to be no big deal?
Another great and informative question to ask. You’ll learn what things stress him out and how he deals with his stress. This question will also create a chance for a story, and who doesn’t like telling stories about themselves.
24. What’s the biggest doubt you have?
Most people have doubts. Either these doubts are about themselves or the world we live in. This question can lead to serious conversations. Moreover, sharing each other doubts can be a good way of creating a strong bond between you two.
25. Who are some people you only met once but they left a big impression on you?
Another useful question to get to know your guy a little better. Now it’s your time to learn if he has met someone that changed his outlook on life?
26. Who is your favorite author?
It may seem a bit generic question but you can actually learn a lot. You can find out how much he is into reading and what type of genres are his favorites. You may even find out that you are into the same fiction stories or autobiographies. If he is not into books and does not have a favorite author that’s also useful to know!
27. When you are day dreaming, what do you dream about?
Everyone dreams from time to time. We all have our secret dreams. This question helps you to find out what goes on in his mind when his eyes glaze over.
28. What was the weirdest habit you had as a child?
Most kids do all kinds of silly or weird things. I’m sure your guy had some weird habits when he was younger. So now you can learn about silly and embarrassing things he did in childhood.
29. What’s the most unusual but fun experience you’ve had?
This is a fun question to ask. Why? Because most guys can do some dumb things in order to have fun. Well, now is the time to learn more about the guy you like.
30. What signs make you think someone will go on to be successful?
This seems like a simple and straight forward question, but it actually tells you a lot about what traits he values in other people. And it can also tell you a lot about what he thinks success is.
31. What do you believe even though you know it’s probably wrong?
This question can lead to some interesting and unexpected answers. I believe it’s a deep question and will make him think a little. I think everyone should question about their beliefs from time to time. The answers may end up a bit serious and dark but they will help you know more about the guy you are interested in; and that’s what these questions are for.
32. What did you think was silly until you tried it?
This question reminds me of green eggs and ham. I am pretty certain that your guy has experienced a green eggs and ham moment at least once in his life. It’s a fun question to keep the conversation going.
33. What was the worst purchase you’ve ever made?
This question is sort of random but may lead to interesting answers. It’s a casual question, however, you may end up learning about something you should not spend your money on.
34. If you could become the number one expert in one field, what would it be?
It’s a perfect question for finding out more about his goals and interests in life. You’ll learn something new about him and who knows, you both might even share the same interests in particular field. Or you’ll learn something new you haven’t known before.
35. What stories from your life would you like to tell your future children?
An awesome question to ask that can lead to some interesting stories about his life.
36. What is your closest close call?
This is another question that makes him to tell you a story. It will help you know more about him. However, it can also dig up some unwanted memories about an incident so use this question with caution.
37. What is the one question to ask someone to find out the most about them?
This question requires a little thought but is great on a lot of levels. It would make the question even more fun and useful if you guys both come up with one question and both answer it. It can lead to some interesting conversations and you’ll both learn more about each other.
38. If you died today, what would your greatest achievement be?
This is a hypothetical question that everyone should occasionally ask themselves. Life is supposed to be lived because eventually we all die. So we should enjoy the time we have now. With this question, you’ll learn more about him and what he thinks his biggest accomplishments are as of now.
39. If you had to choose one cause to dedicate your life to, what would that cause be?
This is another fun question to ask and get to know your guy a little better. We all have some causes that are important to us. Now is your chance to learn what causes are significant to him and if he is active with volunteering or charity or if he wants to be.
40. What do you think you know a lot about but probably don’t?
Most people like to think they are all experts at a lot of things. However, most of the time that’s not true. We are actually average or even below average. For example, many believe they are above average drivers etc. It’s a fun question to think about. You may even get a good laugh out of it.
41. What would you do and not do for 5 million dollars?
That’s a fun question for both of you to answer. Not all questions need to be serious. Moreover, this question can actually tell you a lot about the character and what the guy is about (what morals and activities he finds most important and what are least important).
42. Which celebrity would make the worst president/leader of a country?
This is an entertaining question to think about. I’m sure you’ll both get a good laugh of thinking about different celebrities and what laws they would enforce and what not. Keep switching out the celebrities and keep the conversation flowing.
43. What is the most interesting piece of trivia you know?
Great question that gets him to show off some of his knowledge, and hopefully you get to learn some new stuff. Try to get him to tell you things about a topic you don’t know well. In this case, it would be a win win for both of you..
44. What movie do you wish life was more like?
This is an unique question that would bring out some interesting answers. This is a fun way for both of you to dive into some great movies and think about how your life would change.
45. What long shot have you taken that really paid off?
This is a deeper question and most likely needs time to think about. You have the chance to learn more about his life and aspects you didn’t know about him.
Check out our other article: How To Flirt With A Guy.
46. How old were you when you kissed a girl for the first time?
This is a quite innocent question to ask a guy to get some fun pieces from his past. The answer doesn’t necessarily mean too much but it can break the ice and get you two talking.
47. What do you notice first when you meet a new girl?
This question helps you get a better idea what type of girls your crush likes. It can also reveal a lot about a guy. If he notices girls only for their physical appearance or comments on their particular body parts, you may want to think twice if you want to get to know this guy some more.
I’m not going to lie that most of us notice the physical appearance first but if this is the most important quality a guy treasures, then you might want to choose differently.
48. How would you describe your “dream” date?
This is yet another fun question to ask to get an idea of what your crush likes to do on a date. It can reveal many things about a guy, either if he likes outdoors, romantic picnics on the beach or if he’d rather drink beer and watch a movie at home.
However, don’t take this question too seriously. Guys and girls have usually different ideas of romance. As long as if it’s a quiet place where the two of you can talk to each other and get to know each other better, is all good.
49. Do you like to work out and how often do you work out?
This question shows you if your crush likes to be active and how important this is for him. If you both like to work out then this is something you can enjoy doing together.
Be aware though, if he needs to work out everyday for 3 hours, you may have a hard time dating him. Just make sure you are important to him and he makes time for you too. If he only hangs out with you when he doesn’t need to go to the gym, you may want to ditch that guy.
50. What makes you happy?
It’s a simple question but it can reveal a lot about the guy. Most people’s goals in life are happiness. However, happiness can mean different things to different people. Some would like to be rich, land a dream job or start a family. People work their entire lives to pursue their happiness so this is your chance to ask your guy what things make him happy.
Keep In Mind There Are Some Things You just Can’t Control – Ease The Pressure
A. You BOTH need to take responsibility for the flow of the conversation. It’s a give-take deal and if you have to pull teeth to get him to talk and you’ve given it some time, you’re going to have to decide whether or not to call it quits. After the little bit of awkwardness is out, you need to be able to converse fairly smoothly. It’s definitely not going to get any easier.
B. You can only control his reactions to a limited extent. Don’t be too careful with what you say or it will backfire and that’s not fun.
C. Take everything with a grain of salt. Until you learn better how the other communicates, there’s bound to be some miscommunication up front. Keep your mind open to this.
These are just a few questions you’re going to want to ask your guy before you open yourself up to getting too attached. That way you’ll at least have a decent shot at picking the guy that “fits.”
Don’t Ask Him These Questions
1. So how come you’re single?
According to Time, there’s no better way to make a guy feel like a failure than to ask him why he’s single. This also puts him in a tough situation on how to answer it? Should he tell you he’s picky and very selective? Or should he try and fill you full of hot air telling you that he’s been waiting for you! He could tell you that because he’s in no rush for a major commitment, the girls get bored and move on.
None of these responses will serve him well or change that fact he is indeed single. Think of it this way, if he wasn’t single you wouldn’t be asking him any questions.
2. You’re really cute. I’m wondering why someone hasn’t snatched you up already?
Again, this is the perfect way to make him feel crappy about being single. Nice that you paid him the compliment but why did you have to stab him after? Keep the questions positive and informational; and ball-kicking isn’t positive.
You could comment that you are really lucky someone hasn’t snatched him up already. That would make him feel good.
3. What kind of girls do you like?
Really? Did that just come out of your head? What if he tells you his last girlfriend looked like Selena and you look like plain Jane? All you’re going to do is feel insecure. In fact no matter what he describes if it’s not exactly like you, it’s going to make you feel crappy. So do yourself a favor and don’t ask him this.
It really doesn’t matter his “type” because it’s you he has his eyes on.
4. So do you like skinny/black/big breasted girls?
When you ask a guy about a specific feature in a girl, you are asking for trouble. There’s a zillion ways to skin a cat and it takes more than one “feature” to make a girl. The guy knows you are either trying to see if he’s okay with you not having big boobs or a stick figure body, or maybe that you’re insecure about having particular features.
Either way it’s fishing for information negatively. Just don’t ask the question.
5. How come your last relationship ended?
Slow down here because if all goes well and you actually make it to dating status, you’ll get to ask the question and you’ll likely get a nice straight up answer. It’s better not to make things too serious out of the starting gate.
6. Tell me, do you live alone?
This one is even worse if it’s the guy asking the girl – talk about tacky! However, it’s best not to ask him if he lives alone upfront. What happens if he is living with his mom? Do you really want to go down that road off the hop?
7. Are you a good kisser?
Talk about a subjective question. Even if he’s a crappy kisser he’s not going to say, “Well I’m a pretty crappy kisser.” On the flip side, if he’s an amazing kisser he’s not going to tell you this. Do yourself a favor and skip the kissing question and you may have a shot actually finding out for yourself!
8. How many sexual partners have you had?
EEEEK! Are you kidding me? This sort of question might come into play after you get to know each other and are comfortable and really opening up. What if he’s had 50 different partners? Do you really want to know that? I think not!
Don’t open up a can of worms that’s only going to put him on the spot and create a negative taint at best. You may be curious but leave this one alone.
9. Is Google right about you?
According to Goodmenproject.com you just don’t talk about that sort of stuff when you are testing the waters with a guy. Sure, most girls will do a Google search when they’re researching a prospective guy. However, talking about your top secret findings is a no-no.
If you’ve found something out on Google that you’re curious about, make sure you cleverly scoot around it to probe further but don’t ever ask him directly about doing the custom search; that’s tacky.
10. How much money do you make?
This is another classless question. All it does is leave you looking like you’re basing your impression of him on how much money he makes. Sure, money may be important to you but it’s not something you ask when you are just getting out of the starting gates in the dating department. Hold off on this one until you’re sure there’s some sort of connection. And if this is the kind of question that’s a potential deal breaker for you then you are in for some serious trouble in the dating world regardless.
11. Are you friends with any of your ex’s?
This can be a great question or a crappy one, depending on your personal experiences. Let me explain. If you’re a drama queen and talk trash about all your ex’s, then if he tells you that he’s friends with his, you’re going to be wondering what the heck is wrong with him. Naturally, you will use your personal experiences to cast judgement on him. Not fair but that’s the way the mind works.
Does it really matter if he’s friends with his ex’s or not? You either choose to trust him or you don’t. For many people an ex is an ex for a reason and they just won’t ever go down that road again no matter what the circumstances are.
12. How come you haven’t friended me yet?
Here comes the social media stuff where you can watch his every move. This is just not a good idea when you are figuring out whether or not this guy is a good catch. If you bombard him and steal all his personal space, infiltrate into his personal circles, and make him feel like you are crowding him too fast, there’s really no way he’s going to see that as a positive sign.
Relax on all the personal media stuff and wait until the right time comes to bring it up. Perhaps a month or two from now if this one sticks!
13. How old were you when you first had sex?
What does it matter? This is going to put the guy on the spot and make him worry about what you might think before he even really knows you. It’s best to start in the now and not worry about what happened long ago. Maybe he was 13 and lost it to his neighbor and childhood friend? What good does it do you to know that now?
Perhaps he can’t remember or it hasn’t happened yet?
That’s choosing to travel down a very dangerous road – steer clear of it for now.
14. Do you think size matters?
Just don’t! This tells him that size does matter to you and it’s a subjective question so please just keep it above the belt. There’s no need to embarrass him…again.
15. Do you ever want to get married and have kids?
The fastest way to turn a guy off is to ask that question. People are allowed to change their minds, so what he tells you today might be completely different 6 months from now. This is a “future-date” question. Keep it under wraps until you have connected and feel you might have a future together.
16. What are your thoughts on religion?
This is much different than asking him about religion to try and figure out whether or not he is extreme in his beliefs. We all know that religion is fuel to the fire. It’s a place where logic and emotion intermingle and more often than not create biased and absolute stress. Just don’t go down that road when you are initially figuring someone out; not if you don’t have to anyway.
17. What do you think about abortion?
Healthy Living says you are totally messed up to ask this question. Talk about one of the most controversial subjects on the planet. It’s safe to say if you ask this question you really don’t want a relationship, just someone to argue with.
18. Are you a fan of love at first sight?
This is another cliché you just don’t want to ask. All this does is put external pressure on the situation because he’s now thinking you are expecting it to be love at first sight. Just another question that’s going to push him away before you even get started.
Do yourself a favor and just don’t ask it.
It’s critically important to know good questions to ask a guy when you are looking for the perfect date. But it’s equally important to know what not to ask to turn him off. Make sure your questions are genuine and although you need to push the boundaries a little bit to tap into some emotions; essential to see if there’s a connection, don’t open the flood gates!
Find your balance and learn by doing it and it won’t be long before you find a keeper!