40 Flirty Would You Rather Questions To Ask A Guy

By on May 26, 2014

Oh, great. Another boring game of silly “Would you rather?” questions. Or…is it? Not with these enticing and totally flirty questions! Amp up your game and surprise your crush with these incredibly flirty “Would you rather?” questions he will actually enjoy answering!

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1. Would you rather kiss a girl or be kissed by a girl?

Some men like to be dominant while others like a girl who can step up to the plate and make the first move. This question will let you know a bit more about his personality, and hey- who doesn’t love to talk about kissing?

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2. Would you rather have one partner or several at once?

There are those guys who love to pamper their girlfriend and love her like no other- and then there are the ones who wish they could have 7 different girlfriends, one for every day of the week. What type of relationship does he prefer?


3. Would you rather have a long term relationship or flings?

Again, this is not only a fun and flirty question, but it also gives you a few hints into what type of man he is. A guy who would prefer flings is probably not somebody you want to get involved with in the future (for obvious reasons, unless of course you’re looking for a fling too) while someone who loves long terms relationships will probably treat you better.


4. Would you rather have a hot girlfriend or an OK girl with a great personality?

If he takes the hot girl, he might be shallow. If he wants the girl who’s not overly good looking but has an amazing personality, he is someone who looks beneath the surface. This is definitely a fun question you’ll want to know about the guy you’re talking to!


5. Would you rather check out a girl from the front or the back?

Is he a ‘boob guy’ or a ‘butt guy’? Maybe he’s a ‘stomach guy’? Or maybe he’s one of the rare few that prefers to see a woman’s smile over anything else? You won’t know what he likes until you ask him this cool and flirty question.


6. Would you rather go out for your date or stay in?

Does he prefer romantic nights cuddled on the soda with your favorite movie, or would he rather go out and about on the town for dinner, drinks, and a show? This not only says a lot about the kind of guy he is, but can get you excited about a potential date with this guy!9dc87f996b5e537f1cfd8ba120ffc87e

7. Would you rather find true love or be rich?

Some people aren’t into the love game- some people don’t even believe it exists. Is the guy you’re talking to looking for love or would be rather get his happiness from wealth?


8. Would you rather kiss a girl on her cheek or her lips?

He might be the kind of guy who just likes to give his girl a cute and sweet little peck on the cheek, or he might want to devour her with his lips. You won’t know until you ask him!b365691167cbe5ca9ca389c43f87bcbb

9. Would you rather date someone older or younger than you?

This is just a fun question. I mean, you could find out he likes ladies over 20 years older than him (maybe that’s his fetish) or that he likes them around his age group. The more you know, the better.


10. Would you rather see a girl in a short dress, shorts, or a skirt?

Every guy has different tastes in what they like to see women wear. Find out what he prefers and wear it around him to really catch his attention!


11. Would you rather your girlfriend wear red lipstick or pink lipstick?

Does he like that red hot woman with lots of attitude, or does he enjoy a sweeter more innocent style? This is a great, flirty question to ask and you can find out what kind of makeup you should wear around him.


12. Would you rather do it in a bed or in a car?

Hey, some guys like a little adventure in their sex life! Are you talking to one of them?


13. Would you rather kiss a girl on the first date or wait?

He might be old fashioned, or he might be quit to jump into it with his lady friend. Find out what kind of guy he is with this easy question.


14. Would you rather get back with your ex or find someone new?

Some guys are still holding on to old flames. If that’s the case, you might want to forget about trying to be with him. But if he says he is looking for someone new, then keep asking him plenty of questions- you could be his next love!


15. Would you rather date me or be my friend?

This is a personal one- and we have to warn you, be ready for the answer. You might find out he has a secret, passionate love for you, or he just simply thinks of you as a great friend. Wouldn’t you like to know how he feels while still asking in a flirty and fun way? Of course!


  1. Would you rather give a massage or receive a massage?

Some men really love making sure their woman is relaxed and loves to treat them like queens. There are some who enjoy being the one treated like royalty, but it’s good to find a balance between the both of you. Figure out if he is the type to pamper by asking him this sensual would you rather question.


17. Would you rather a girl or a guy make the first move?

Getting the answer to this question is important, especially if neither of you have made any moves. We already asked him who he prefers to initiate the first kiss. Now you can get a feel for what he prefers when it comes to making the first move on things like the first time you two make a date. Is he a shy type or does he just prefer confident girls? Maybe he wants to make the first move. Find out by asking!


18. Would you rather a girl wear lingerie or just be completely nude?

Does he like it when you get dressed up or dressed down? Become a little bit more flirty by talking about what he likes when it comes down to the bedroom. These types of questions seem to ignite a man’s interests,  keep things heated between the two of you and build the right kind of tension with him.


19. Would you rather cuddle or makeout?

This question is definitely one of the flirtiest. It gets him thinking about you the two of you spending time together in the most intimate ways and his answer might bring a smile to your face. Is he a soft cuddly type or a more hands on guy? You would like to know, wouldn’t you?


20. Would you rather sleep naked or with pjs?

You’re pretty much asking if he is the kind of guy who likes to let it all hang out with no worries or if he likes to stay comfortable and clothed at night. It will give you a look into what you would be dealing with if you share a bed. Maybe you like to sleep naked, too. It is good to be sure you are both on the same page, although we highly doubt he would have a problem with you sleeping in the nude either way.


21. Would you rather have kids first or get married first?

It seems like a silly thing to ask, we know. But it is a good question, especially if you are really trying to get to know each other. Is he more traditional or does he want to break outside the box. Where do his responsibilities lie? Although it’s not the most lighthearted question, it is a good one to ask a potential partner.


22. Would you rather cook or be cooked for?

Maybe he has the skill of a young, hot Gordan Ramsey when it comes to the kitchen. Asking if he cooks is a light, flirty question because it gives him an idea of the two of you doing something intimate together like cooking. Maybe he likes picturing you cooking supper for him or vice versa. Food and cooking generally tend to help bond people, so it’s a great subject to touch on.


23. Would you rather be purely physical or make a commitment?

Does he want to take things to the next level or is he trying to keep it casual? Obviously bringing up sex in any question keeps flirtatious levels to the max, but who says you can’t get an idea of if there is a future there or not. Maybe he really likes to smoosh but isn’t ready to be boyfriend material. You’ll never know unless you ask!


24. Would you rather be with a short girl or a tall girl?

Just like the boobs or butt question, this question will give you an idea of what type of girls he is into.


25. Would you rather go camping or stay in a hotel?

Start daydreaming together by discussing what you would do on potential future dates. Is he an outdoorsy type or does he want to take you for a night in the city? It’s sexy to think of romantic getaways, don’t you think?


26. Would you rather go on long walks or long drives?

Again, discussing what you two would do on your dates gets the gears turning and gives you two a look at what being together would be like. Keep the blushing coming by asking each other questions like these.


27. Would you rather date a good girl or a bad girl?

The answer may surprise you. Does he picture himself with a bad to the bone man-eater or a down to earth good girl? Get his wildest fantasies out in the open and watch the flirting get taken to a whole new level.


28. Would you rather cuddle and watch movies or go out and adventure?

Does he love the idea of spending a day inside curled up with you? Or does he want to take you out on a grand adventure? Either way the answer should get you feeling all warm and tingly inside, not to mention get you both excited for days like that to come.


29. Would you rather we talk through text, calling or social media?

These days it is hard to know right off the bat what someone’s preference for communication is. You may want to ask this question so you know the best route of talking with each other. Usually apps where emojis and gifs are available are preferred because it brings in visuals when you’re flirting.


30. Would you rather date a good kisser or a good lover?

Mmmm always a flirty idea to bring up kissing or being together romantically. It will build tension between you and let him know what you have on your mind. This question is more to the silly side because hopefully he will think you are both a good kisser and a good lover. But, if he had to choose, which would it be?


31. Would you rather break up with someone or be broken up with?

Maybe he is a bit sensitive and can’t handle the task of breaking it off with someone when the time comes. Get a feel of how he handles a serious situation by asking.


32. Would you rather give up your favorite food or give up sex for six months?

This question is sure to get some laughs out of the two of you. Would he give up his favorite food for you? It’s important to know, right?


33. Would you rather be with a girl who has a great work ethic or a girl who plays hard?

If he had to choose one, which would it be? Does he prefer a girl who works extremely hard or one who has a good time. Maybe he really wants both.


34. Would you rather take a vacation with me or a vacation with your friends?

Hopefully he doesn’t screw this one up by answering incorrectly. Sure, taking a vacay with his friends would be fun, but the goal is to make sure he wants to take you on a vacation! If he does answer correctly, it opens up the door for you both to reminisce what getting away together would be like.


35. Would you rather date a girl who surprises you or a girl who is blunt?

Pick his brain a little bit so you know in the future what he prefers. Some people really love being surprised by things while others truly detest it.


36. Would you rather be with a girl who loves your friends or one who loves your family?

In a perfect world, the answer would be both. Unfortunately, that is not always the case. Sometimes you just can’t get along with the crew and the fam both. So dig in and figure out what one is more important to him. Also, consistently bringing up dating is definitely the right flirtatious route to take if you really like this guy.

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37. Would you rather have a shotgun wedding or a large, planned out wedding?

We know, we know, you probably aren’t anywhere near ready for marriage. But, this is a fun question to ask and get an answer for. You both can talk about your dream weddings and if he isn’t into it, move on to number 38!


38. Would you rather be rich and famous or be a nobody yet be happy?

This is a great would you rather question, while also giving the conversation some sentimental aspects.  It gives you an idea of where his priorities really lie and if he is the right man for you.


39. Would you rather eat at a restaurant or eat at home?

They always say the way to a man’s heart is to his stomach, so figure out where the right place to feed him is, while keeping the conversation flirty and fun at the same time.


40. Would you rather give or receive in the bedroom?

Spice things up with this racy question and get a feel of what he’s going to be like in the bedroom. The two of you will love talking about how to please each other and it is sure to get your blood boiling in all the right ways!



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