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125 Things to Ask to Keep You Talking

You might worry about spilling wine on your dress, or choking on your pasta, but more often you worry about keeping the conversation going.

Most women find themselves talking more than their date, and for good reason. Guys tend to clam up when they’re nervous. It’s the “deer in the headlights” effect. They see a beautiful woman in front of them and BAM! There goes their brain.

Because of this, ladies, it’s up to us to keep the flow going, and the only way to do that is to ask your guy questions. There are two types of questions in this world: Open-ended and closed-ended. A closed-ended question can be answered with a simple “yes” or “no” and leaves no room for conversation.

However, if you ask a series of open-ended questions, you and your guy could be chatting away for hours on end.

For those who need help coming up with ideas, I’ve created the Ultimate Guide of questions to ask a guy. Some of these are first and second date questions…and some of these are further in when you’re ready to open up physically and want to know all your man’s hot spots!

So here you have it! All the questions you’ll ever need for the dating scene and everything you need to keep the conversation going. Good luck and happy dating!

Questions to Ask a Guy to Get Him to Open Up

Questions to Ask a Guy to Get Him to Open Up
Questions to Ask a Guy to Get Him to Open Up

Sometimes we meet a man who is everything we want in a guy, he’s funny around friends, he’s intelligent and he’s easy on the eyes. The problem is, this guy might be great in a crowd, but once you get him alone he has no idea what to say or how to say it. How do you get him to be less shy around you? You ask him these questions.

The first set of questions is for a casual conversation. They can be used on a date, but it isn’t necessary to wait until then. In fact, you can ask these anytime you meet a guy you’d like to try and get to know. Met him on a bus or plane? These questions will work for that! Met him on the treadmill beside yours at the gym? Again, we’ve got you covered!

The trick to casual conversations is to make sure you keep the conversation going. Ask him an open-ended question (see questions below) and listen intently, then follow up with an open-ended question about his answer. For example:

  • You: So, what is your favorite gaming platform?
  • Him: I miss the old ATARI
  • You: Me too! I loved Pac-Man and Pitfall. What games did you like?

Do you see how that flowed? You asked an open-ended question, he responded, and you kept the conversation going with a response that reflected his answer while giving a little tidbit of information about yourself as well. These twenty-five questions to ask a guy will keep it casual and flowing without getting too personal (just in case you don’t like his answers).

#1 Where Were You Born?

This is a good date question. (It would sound a little creepy as the very first thing you ever say to him.)

#2 Do You Have any Brothers or Sisters?

This one is also a good question for later in the conversation.

#3 What’s Your Favorite Movie?

You can’t go wrong with this conversation starter.

#4 What’s Your Favorite Food?

Don’t ask this one at the gym.

#5 What Do You Think About (insert random sports event)?

Sports are a safe conversations starter, and if he doesn’t watch sports you can always follow up with, “Oh, what kind of things are you interested in?”

#6 What Do You Do for a Living?

Great for sitting next to a hottie on a long flight.

#7 Are You a Night Person or a Day Person?

Random and a little spontaneous.

#8 If You Could Have One Superpower, What Would it Be?

Always a good question; most people WANT to answer this one.

#9 Are You Allergic to Anything?

Save this one for the date.

#10 Do You Like Red or White Wine?

Also a date question unless he’s ordering a drink on his long flight.

#11 Who’s Your Favorite Author?

Endless possibilities.

#12 What’s Your Favorite Book?

A great way to make conversation if he’s reading something.

#13 Who’s Your Favorite Movie Star?

Ways to tell what kind of movies he likes.

#14 What is Your Favorite Kind of Car?

Most guys love to talk about their car.

#15 Do You Golf?

A lot of men golf. I don’t understand it myself, but there it is.

#16 Do You Play Video Games?

Probably a yes questions…to be followed up with:

#17 What is Your Favorite Video Game?

If he said “no” to the above question, ask him this:

#18 Do You Like Board Games?

Or, you can ask him this:

#19 Can You Play Poker?

Very convenient if you’re on a trip and you happen to have a deck of cards with you!

#20 Can You Play Chess?

A good intellectual conversation starter.

#21 Do You Know Any Magic Tricks?

This is especially fun if YOU can show him a magic trick!

#22 Do You Like Tea or Coffee?

A safe long trip or date question.

#23 Do You Have any Pets?

You can ask this one anywhere.

#24 Have You Ever Had any Pets?

Only use this one if he says “no” to the question above.

#25 What is Your Favorite Animal?

A date question. Not a particularly good opening question, so save it for the date.

Any question you would be willing to ask a stranger on a long bus ride is a potential question to ask a guy in order to get him to open up and talk to you. These are the opening lines, in a manner of speaking. They’re also particularly geared towards men who are shy and don’t know how to make conversation or who don’t know how to talk about themselves and their own interests.

One of the most important things to remember about these questions to ask a guy is that you must respond with a little bit of information about yourself. It really isn’t enough that you’re letting him talk about himself; you also need to be open about your own interests so that he gets to know you. While it can sometimes feel like men only want to talk about themselves, the truth is any man who is even remotely interested in you will want to hear what YOU have to say as well.

Questions to Ask a Guy On a Date

Fashionable young urban couple going out on a date

What happens when you sit down in front of him over your plate of pasta and glass of wine and he looks blankly at you as if you’ve never even met before? How will you keep the sparks flying (or the conversation going) if your dear has become a deer?

Date questions are a little bit different than “stranger” questions. By the time you get to the point you’re going to go on a date with each other, you should already have a few sparks flowing between you. That’s how it should be! You should feel some sort of mental chemistry from the first set of “getting to know him” questions above.

But now, it’s time to take things to a different level.

These questions can be used for the first couple of dates so that you and he have something to talk about as you two continue to get to know each other. You should be lighthearted and have fun when asking and answering the next set of questions with your guy.

Don’t be put off if he doesn’t have the same interest as you. In fact, at this point in the blossoming relationship, you should just have fun and keep the words flowing. I highly recommend taking advantage of any opposing hobbies or ideals to learn something new.

For example, if your guy likes playing the guitar and you are not musically inclined in the least, invite him to show you a couple of chords sometime or ask him to play something for you. If you’re an avid knitter and your guy has no interest in knitting, offer to show him something you made or give him some strange knitting trivia he likely wouldn’t know. The right kind of guy doesn’t have to like what you like, but he does have to like you (and all of your interesting little tidbits as well).

#1 If You Could Work Anywhere, Where Would it Be?

Maybe you both wanted to be an astronaut when you were little!

#2 Who Do You Admire Most?

An easy way to learn more about him as a person without having to ask him something personal.

#3 Do You Like Musicals?

If yes, you can talk about Oklahoma all night! If no…move to the next one.

#4 Do You Like Museums?

I know a lot of men who are huge history buffs!

#5 What is Your Favorite Kind of Art?

If he has any kind of brain, he’ll like some kind of art form. It could be anything from comics to Claude Monet.

#6 Where do You Like to Eat?

Easy, simple, and everybody eats so you can’t lose.

#7 Can You Cook?

Ooooh, maybe he’ll say YES!

#8 Do You Like to Work on Cars?

If yes, he’ll talk about cars for the next hour.

#9 Do You Have Any Hobbies?

Most people have a hobby, even a failed attempt at a hobby.

#10 Do You Ever go to Carnivals?

Not relative if you met at a carnival or you’re there with him now.

#11 What is Your Favorite Carnival Ride?

He’ll either name one or he’ll say they all make him sick.

#12 What is Your Favorite Carnival Food?

Funnel cake is the most common answer.

#13 Do You Like Concerts?

Believe it or not, some people don’t.

#14 Do You Like Rock or Country Music?

We can only hope he likes the same music as you.

#15 Who is Your Favorite Musician?

With any luck, you’ll have heard of the band he names!

#16 What’s the One Thing in The World You Want Most?

If he says “you” on a first date, it’s time to be creeped out.

#17 Do You Have any Tattoos?

You know you’ll have to probe for details if he answers “yes”.

#18 Do You Have any Piercings?

See above.

#19 What was Your Worst Job?

Oh, the stories you’ll hear!

#20 What Job Was the Most Fun for You?

A quick way to make him smile – unless he’s always hated his jobs.

#21 What is Your Favorite Color?

Remember it for later dates, but don’t wear it on date two.

#22 Do You Have a Favorite Superhero?

Most likely…some guys really aren’t into superheroes, though.

#23 What Kind of Junk Food Do You Like?

The man MUST have a weakness!

#24 Have You Ever Met Anybody Famous?

If he says no….ask:

#25 Have You Ever Met Anybody Infamous?

Smile when you ask him, maybe he’ll laugh at your humor (if not, do you really want a guy with no sense of humor?)

Remember, make sure you follow up with a few interesting facts about yourself or else he’s going to think you’re interviewing him (which is not attractive at all!). Also, for the first few dates, you’re definitely going to want to keep the conversations light and easy. These questions should be friendly and upbeat! Do not use the sexy set of questions for your guy yet (those will come out later), and don’t give him the third degree about his religious or political beliefs. Use these for fun and friendly conversation.

Questions to Ask a Guy to Get to Know Him Better

One of the most difficult parts of any budding relationship is trying to get to know a guy better (outside of Facebook stalking him and following him on Twitter).  It’s hard to know what questions are appropriate and what questions a man might find too personal. Some men think that a first date should be full of inquiring questions about his past and his family, while there are other men who won’t even talk about their previous relationships until well into dating you.

Every man is different.

Still, there are always those questions to ask a guy that are inquiring and yet still neutral enough not to cause offense. The following questions are great ways to not only find out a little more about your fella’s past, but also an excellent way to satisfy your curiosity about him without being outright intrusive. Men can be very sensitive when it comes to their secrets.

#1 Where Did You Grow Up?

An excellent conversation starter.

#2 Have You Ever Traveled?

If so…

#3 Where Have You Lived?

You can compare places.

#4 Who is Your Favorite Person?

Hopefully it’s his mom.

#5 What is Your Horoscope Sign?

A test of true compatibility…

#6 Do You Believe in Horoscopes?

Okay, maybe not.

#7 What Are Your Parents Like?

AKA is his family as crazy as yours?

#8 Do You Have a Bucket List?

If not, perhaps he has a short “To Do” list?

#9 Name One Thing on Your Bucket List?

See above.

#10 Did You Go to College?

Do you have rival teams?

#11 What Was Your Favorite Subject in School?

A key insight into who he really is.

#12 Do You Like the Ocean?

He might be more of a mountain man.

#13 Do you Like the Summer or Winter Better?

Plenty of ways to keep this conversation going.

#14 Do You Play Any Sports?

If no…

#15 Do You Watch Sports on TV?

If yes…

#16 Who is Your Favorite Team?

If you don’t know them, just say “Ah, cool.” And move on.

#17 What’s Your Favorite Cereal?

Everybody has a favorite cereal.

#18 What Makes You Relax?

If he says “drugs” or “alcohol,” it’s time to walk away.

#19 What’s Your Favorite Thing to Snack On?

Hopefully something more interesting than celery.

#20 If You Could Change Your Name, What Would You Make It?

Now THIS one will make him think!

#21 Would You Rather Be a Good Guy or a Bad Guy in a Comic/Movie?

I’m not sure I’ve ever met anyone that said “good guy.”

#22 Who’s Your Favorite Villain?

Lex Luthor, Doctor Octopus…there must be a villain he likes?

#23 What Was Your Best Day?

He shouldn’t take too long to think about this one.

#24 How Did You and Your Best Friend Meet?

Sometimes it’s a fascinating story…sometimes it’s “we met at work.”

#25 What Were You Like as a Kid?

Always a good insight into a guy! Plus, you’re now imagining him all cute and mischievous, aren’t you?

Remember, getting to know someone comes with time. I know partners who have been together for decades and are still finding things out about their lover. People are such fascinating creatures, aren’t they?

If you want to speed up the process of getting to know him better (or if you just need to find something else to talk about), here are twenty-five more questions to ask a guy that will help you get to know him on a more personal level (thereby knowing the “real” him). None of these questions should be considered too much information to give, so you can feel completely comfortable asking them.

Questions to Ask to Determine if He’s the Right Guy

Profile view of an attractive young couple sitting staring intently into each other eyes

There are many different things that even the most incompatible couples can move past. For instance, most people can generally agree on where to live, or even what type of home to purchase for that matter. You can even make things work if he’s a sports fanatic and you’re a bookworm.

But there are certain things you cannot ignore when it comes to finding Mr. Right. If you dream of living on a farm in Kansas with twelve kids and a cow, but your guy longs to live in an upscale flat in New York city with no kids and no pets, then one of you would have to do some major sacrificing in order to make your relationship work.

Sometimes, no matter how much you love someone, you just can’t spend your life with them.

The next set of questions to ask your guy is designed to really delve into the kind of future your man has planned and whether or not you can see yourself with this person. You’ll ask questions about his goals and his dreams and you’ll be able to compare them to your own.

You’ll also use this section in order to really delve into his past a little bit more. Knowing your partner’s plans for the future is one thing, but you also need to know his history. There are a few reasons to know your guy’s past before fully committing to this relationship. The following twenty-five questions are the ones you’re going to want to ask your guy before you sleep with him and before you decide to commit to him.

#1 Do You Like Kids?

It’s an honest question.

#2 Do You Want Children?

Definitely an important question if you’re planning a long-term commitment. You want to make sure you’re in agreement.

#3 What are Your Religious Beliefs?

This is very important to some people.

#4 Have You Ever Been in Jail?

Might be a deal-breaker…might not.

#5 How Often Do You Drink Alcohol?

Another potential deal-breaker.

#6 Have You Ever Tried Illegal Drugs?

You might be okay with the answer, or you might find out he’s a crack addict. Best to find out now.

#7 Do You Smoke?

#8 What Are Your Political Beliefs?

This could cause problems if you’re both very passionate about opposing sides.

#9 Do You Save Money or Spend Money?

You don’t want to be with a man who is going to sponge off YOUR money!

#10 How Do You Feel About Women’s Rights?

Believe it or not, some guys don’t think women should have any rights.

#11 Are You a Go-Getter?

Remember, lazy is bad.

#12 Do You Believe in Monogamy?

Make sure your views match. Trust me on this one.

#13 Do You Believe in Marriage?

Again, he’s not likely to change his opinion.

#14 Are You Romantic?

Ask, but pay more attention to his actions than his words.

#15 What Do You Look for in a Partner?

If he’s looking for a supermodel, you might want to be wary.

#16 Have You Ever Stolen Anything?

As an adult, a pack of gum from the shop when he was five really doesn’t count.

#17 Have You Ever Had to Tell a Lie?

Again, use the right context; little white lies to get out of a ticket don’t count.

#18 What Was Your Best Relationship?

Pay attention.

#19 What Was Your Worst Relationship?

Pay even more attention.

#20 Do You Believe in Love?

If he says “No,” you need to walk away.

#21 Are You Temperamental?

Pay attention to his answer, but pay more attention to his actions.

#22 What is Your Biggest Pet Peeve?

You wouldn’t believe some of the answers to this one!

#23 Do You Gamble?

You might not want a guy who’s at the casino every other day.

#24 What is Your Best Trait?

He might say his hair – it happens, just go with it.

#25 What is your Worst Trait?

Always an interesting answer.

By knowing his past, you’re going to be able to delve a little deeper into his psyche. For instance, is he a recovering drug addict? Has he ever had a criminal record? These things do not automatically eliminate him from the list of “good guys,” but they can be pretty important if your own history includes drug addiction recovery or an abusive upbringing.

Also, knowing a man’s past is a way to make sure he’s honest with you. If you don’t know anything about your guy, then you have no idea who he really is as a person. You can’t build a relationship on that kind of secrecy.

Fun, Crazy, Dirty, and Flirty Questions

young couple smiling at each other during a romantic date in the forest

Now that you and your guy have been dating a little while, and you’re sure that he wasn’t an axe murderer in his past, you have probably reached the steamy point in your relationship where you’re ready to get him naked as quickly as possible.

That’s completely understandable. After all, what better way to build up the intensity and the heat than to wait until you and your guy have gotten to know each other before doing the naked tango?

But now that you have gotten to know him better, and you have decided that he’s the kind of guy you want to wake up next to in the morning, there’s an entirely different set of questions to ask your guy: The naughty kind.

The next set of questions to ask your guy focuses on sex. That’s right: This is the “everything you want to know about him naked” section, and there are a couple of ways you can ask him these questions.

What I suggest, however, is to wait and ask him these questions after you’ve already slept with him. Let’s be honest, first time sex is always going to be awkward. There really isn’t any way of getting around that. When two people get nude for the first time and then have no idea whether or not to be creative or romantic…well, it’s kind of a recipe for disaster, really.

Because getting naked can be so weird the first time, use these questions as a sexual ice-breaker. One way to do that is to talk about a sexual preference or fantasy of your own. For example:

  • You: Do you have any secret fantasies?
  • Him: Yeah, doesn’t everybody?
  • You: I think so. Personally, I’ve always wanted to have sex outdoors. It just sounds so thrilling and fun! Have you ever wanted to try that, too?

You see? Asking him flat out what his sexual interests and preferences are might give him the wrong impression. However, asking him a question, giving your own answer to that question, and then waiting for him to respond is going to have a much smoother transition.

You can even ask a closed-ended question after you tell him something sexual about yourself (as I did in the example). Sometimes it’s easier to answer sexual yes or nos than it is to actually give an open-ended answer about your sex life.

Actually, before diving deeper with dirty questions, you should read Felicity Keith’s Language of Desire, the best-selling guide to talking dirty. It’ll really deepen your understanding of the way men think, what makes them supremely aroused and the type of questions to ask that will show you his secret desires.

As for timing, make sure to ask these questions in a curious, but non-judgmental manner. Many people are very private about their sexual history and preferences (especially if they tend to like things a little “out of the norm”). Don’t force him to answer; just ask pleasantly and curiously.

You don’t have to ask every single one of these questions. Seriously, leave something to the imagination or to find out by yourself as time goes by.

Also, if he answers a question and you don’t like his answer, keep it to yourself. You’re probably not always going to agree with his past or his preferences, but unless he’s putting you in harm’s way (or trying to bore you to death), it’s perfectly okay (and very, very normal) to have a different sexual history than your guy. Don’t stress over this one.

#1 When did You Get Your First Kiss?

This isn’t too much to ask, in fact, if he can’t answer this one, then don’t move on with the next ones.

#2 What Was Your Best Kiss?

He better say, “Yours.”

#3 What Was Your Worst Kiss?

He’d better NOT say, “Yours.”

#4 Boxers or Briefs?

The ultimate underwear question….

#5 Would You Ever Visit a Nude Beach?

More importantly, would you be nude on that beach, too?

#6 How Old Were You When You Lost Your Virginity?

Don’t judge.

#7 Secret Turn-On Places?

He may ask you to find out for yourself!

#8 Do You Like Being Tied Up?

Please say yes, please say yes, please say yes!

#9 Do You Enjoy Food with Sex?

See above.

#10 Have You Ever Had a Threesome?

Don’t judge.

#11 Do You Like Playing with Sex Toys?

If he says he doesn’t know, introduce him to some of yours.

#12 Have You Ever Been Attracted to Another Man?

This is a legit question, and if he says yes, then he’s probably very comfortable with his sexuality, which is a good thing!.

#13 What’s Your Favorite Position?

Oh, the options!

#14 Where is Your Favorite Place to Have Sex?

You might want to show him someplace new.

#15 Where Was the Worst Place You Ever Had Sex?

Be prepared to cringe; this answer isn’t always pleasant.

#16 What’s Your Darkest Fantasy?

Should not be so dark that you want to get out of there as fast as possible and call the authorities.

#17 Do You Prefer Women in Lingerie?

If he says, “No,” don’t worry; it just means he likes you better naked.

#18 Do You Like Morning Sex?

If so, then you have a keeper.

#19 Do You Like Sex in the Shower?

Particularly after morning sex.

#20 Where Have You Always Wanted to Have Sex?

Hope it matches yours.

#21 If You Could Sleep With One Person, Who Would it Be?

This one always has an interesting answer.

#22 Where Do You Like to Kiss a Woman?

I think I just blushed.

#23 Where Do You Like to be Kissed?

I bet HE just blushed!

#24 Do You Like to be Spanked?

Please say yes, please say yes, please say yes!

#25 What’s the Kinkiest Thing You’ve Ever Done?

Brace yourself: You have no idea where this one’s going!

While I’m a firm believer in dating conversations taking a route of their own, these are not going to be restaurant appropriate questions. You can ask them as you’re walking down the road hand in hand (and there are no children nearby to eavesdrop on you). You can ask him over a private dinner in your own apartment (or his) after you’ve opened up a bottle of wine and turned on the Barry White CD.

A little bit of advice. When you’re asking your guy these questions, make sure to only choose those questions that you yourself wouldn’t mind answering. If you can’t answer the question, then don’t ask it to him.

Final Thoughts

Two couples shot through window enjoying coffee

Getting to know each other is a major part of the relationship process. In fact, this is what your entire relationship is all about. If you don’t know who your lover is, then how can you be sure you really love them?

Here are a few guidelines to follow with these questions to ask a guy.

1. Always be attentive to his answers and respond with the appropriate enthusiasm or concern. 

If you ask a question to find that suddenly your date is pouring his heart out to you and sobbing over dessert, then you definitely have to pay attention. You can’t skip out and leave by pretending to go to the restroom. If it’s a sad story, be sympathetic. If he’s over excited about his pet snail, be excited with him. If you want to date this guy again you have to be respectful and pay attention to his answers.

2. Always ask open-ended questions whenever possible so that he HAS to answer you and keep the conversation going.

Remember, if you ask a closed-ended question your guy can simply say yes or no and be done with the conversation. That’s all there is to it. However, if you ask open-ended questions, they’ll soon drag him out of his shell and force the guy to open up to you. When he opens up to you, you have a better chance of catching and keeping him (as well as getting to know him better).

3. Never ask anything you wouldn’t want to answer yourself!

If you are going to ask your guy a question, first ask it to yourself. If you would not be able to comfortably give a response to your guy (or anybody else for that matter), then skip the question. One thing I can practically guarantee is that most people return the same question to you in order to get your opinion and views on the matter at hand. If you wouldn’t answer it then don’t ask.

4. Respect his opinion even if it differs from your own.

You might be a liberal-minded woman who lives green, doesn’t own a car, and lives out of a tent, but if your guy hunts whales for a living, owns a Porsche, and stays in a city flat you might be tempted to lecture him. Don’t. Even if this isn’t the kind of guy you would date, never end a potential friendship if you and your guy don’t see eye to eye. Who knows? Maybe he has a friend who is exactly like you he’d like to introduce you to.

5. Respect it if he refuses to answer.

Once again, not all men are comfortable talking about themselves early in the relationship. You are probably going to have to go through a few quiet times and some unanswered questions simply because that’s just the way things go. Don’t keep pushing him for an answer.

Wait until later in the relationship to ask sexy questions!

There are lots of good reasons why I recommend getting to know someone before your sleep with them, but most importantly is that if you want a relationship with the guy, wait to have sex with him. Think of sexy questions as sex itself, something you want to wait on.

These questions to ask your guy should keep the conversations flowing smooth and going strong. So, the only question left is: What are you going to ask him first?

 

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