Home Love & Relationship 40 Flirty Would You Rather Questions to Ask a Guy

40 Flirty Would You Rather Questions to Ask a Guy


When you are in a relationship, you have to find a way to keep the love alive. Whether you are just bored or want to learn more about your boyfriend, these flirty would you rather questions can help. They can help spice up your romance and give you deeper insight into what your boyfriend is thinking. At the very least, they will help you find something fun to do with your boyfriend. If you need some ideas to get you started, check out these 40 flirty would you rather questions to ask a guy.

1. Would you rather see me naked or have me see you naked?

This is a steamy question to ask right away. You may want to warm up with a few of the other questions first if you are playing this game with your crush. If you are playing with your boyfriend though, he may really like this question.

2. Would you rather save your mother or father from a house fire?

This question can be extremely illuminating about your boyfriend’s relationships with both of his parents. No one will hopefully ever be in this type of situation, but it is good to know what he would actually choose to do and why.

3. Would you rather argue and be right or forgive and tell her she is right?

Basically, would he rather stop arguing and be thought of as wrong or would he rather continue to argue just to make his point. This answer could be illustrative about future arguments in your relationship.

4. Would you rather stick to one girlfriend or play the field?

Listen to his answer closely! If you are not dating yet, this answer will show you if he can even commit to being with one person right now. If you are already dating him, he had better say that he wants to be with one girlfriend. If he would rather play the field, then the future does not look very good for your relationship.

5. Would you rather remain a virgin until 50 but get to sleep with your soulmate or lose your virginity early to someone that you don’t care about?

This question could tell you how honest he is. Most people would probably say that they would rather get to have sex early and, in reality, few people would actually wait until 50 to find the perfect person to sleep with.

6. Would you rather have a sexy girlfriend or a brainy one?

This all comes down to his personal feelings. It will also tell you what your chances are with him. If he likes you, he will pick the answer that describes you the best.

7. Would you rather keep searching for true love and keep getting heartbroken or give up after the first heartbreak?

No one likes to go through heartache, but it is the only way to really find the one person who will actually be the perfect match for you. With any luck, you won’t have to have such a stark chose in real life.

8. Would you rather tell your girl the bitter truth or comfort her with lies?

Again, this answer will show what you can expect in your relationship. There is no right answer though—some people would rather hear a comforting lie during a difficult time, and others would rather have their partner be brutally honest.

9. Would you rather have a short-term or a long-term relationship with a girl?

This is another one without a right answer. If you are looking for a fling, then it could be a good thing if he just wants a short-term relationship. If you want to have a more committed relationship though, a short-term relationship would not be what you are looking for.

10. Would you rather make love in the kitchen or the dining room?

You could also mix this question p by picking two random places like in the woods, on a carousel, on the beach or in an alleyway to see what he would say.

11. Would you rather take your girlfriend for a fancy date on a Valentine’s Day or stay home for a romantic evening?

Both activities could be nice. A fancy dinner date is always fun and it gives you a chance to spice things up. Of course, staying at home and cuddling up are nice as well. If he does not like dressing up or does not have a lot of money, he will most likely choose the second option.

12. Would you rather cuddle or make out?

What would your answer be to this one?

13. Would you rather cheat on your lover with your ex or with a stranger?

Ouch. This is going to be a difficult question for him to answer. An ex is the easy answer because you have been with them before, so it is easier to make that transition again. At the same time, it is probably the worst option because you could actually have feelings for your ex. Unless your crush moonlights as a diplomat, he is going to have a hard time extricating himself from this one.

14. Would you rather be single or in a relationship?

If you are in a relationship with him, he should obviously say that he wants to be in a relationship. If you are playing this with your crush, then this question will help you see if it is even possible to have an actual relationship with him for now.

15. Would you rather choose to stay with your girlfriend if it meant you lost out on a chance to become rich?

This is interesting. Wealth can make life more comfortable, but would he be willing to give all of that potential comfort up to just be with you?

16. Would you rather love a disabled lady who loves you back or love a hot lady who does not return your love?

If he says the second option, he might be a jerk.

17. Would you rather be the one caressing a girl or be caressed by her?

You can modify this question to include other things like would he rather go down on you or have you go down on him. You could even switch it to whether he would rather be on top or bottom if you are feeling particularly flirtatious.

18. Would you rather save your mom or your girlfriend if you could only save one of them?

Don’t hate him if he says his mom—after all, she gave birth to him.

19. Would you rather fall in love with someone older or younger than you?

While most guys date someone younger, this does not mean that you have to lose hope if you are slightly older than him.

20. Would you rather cry or stay stoic when faced with a serious problem?

Most people have cried for some reason or another. Let’s see if your crush can be honest about how he actually reacts to a problem.

21. Would you rather make the first move or wait for her to do it?

If you are playing this with your crush, listen closely to the answer. Some guys are extremely shy and would be more than happy if the girl made the first move. If he says that he would rather wait for the girl to make the first move, this could be your hint that he wants you to make a move because he is still not sure if you like him or not.

22. Would you rather make love for hours but only once a week or have short, 5-minute sessions every day?

While the hours-long sessions sound good, their infrequency makes them less than ideal. Tough choice.

23. Would you rather live in the country or the city?

If you are already dating, this question is just another way for you to get to know him better. Plus, it will help you figure out if your future dreams and goals are actually compatible or not.

24. Would you rather have sex with the lights switched on or off?

This is a good thing to know before you guys get too intimate. Plus, it could reveal how he thinks about mood lighting or how comfortable he is about his body.

25. Would you rather marry a doctor or an athlete?

Another follow up question would be to ask him if he would rather magically become a doctor or a professional athlete.

26. Would you rather kiss a girl on the first date or wait until you know her better?

If you are playing this game with your crush, this is a good question to ask. This will also give him a hint that you could be interested in him and would like to kiss him.

27. For a simple fling, would you rather get intimate with a fat lady or a slim girl? What about for a relationship?

This could tell you a lot about his honesty as well as what he wants in a woman.

28. Would you rather fall for a sexy married woman or a widow?

Hopefully, he chooses a widow. Of course, it would be hard to live up to the memory of the widow’s late husband, but it would not have all of the negative social and moral implications.

29. If you discover that the girl you love has had an abortion, would you rather stay with her or break up?

This will tell you a lot about his personal beliefs and the lengths that he is willing to go for his partner. If he hates abortions but would stay with the girlfriend, then he must really like her.

30. Would you rather eat a meal cooked by your mom or a local diner?

This is just a question to get to know him better and is more for fun than anything else.

31. If you are aroused, would you rather wait for your lover to return home a week later or do it with a stranger now?

Hopefully, he chooses the former option and not the latter.

32. Given the choice, would you rather have sex at dawn or at dusk?

Some people are morning people, others are late night owls. Which one are you?

33. Would you rather date a girl who is taller or shorter than you?

Thankfully, the societal norm of having a shorter girl with a taller guy is gradually going away. It’s always better to love the person who is right for you instead of their height.

34. If your soul mate is HIV positive, would you rather continue dating her or call things off?

This is a tricky question. Everyone is naturally adverse to diseases like HIV, and many people would not be able to handle dating someone who has the disease.

35. Would you rather lose your eye for a girl you love or lose it for money?

One option gives you a morale boost, but the other actually gives you a tangible benefit.

36. Would you rather sleep naked or in pajamas?

This could be a good question to learn for your future relationship.

37. Would you rather date a hot girl with a bad personality or an ugly girl with a great personality?

Again, this helps you to understand what he is looking for from any relationship.

38. Would you rather be with a lady of the same race or a different one?

Thankfully, society has changed so that both options are now possible.

39. If you are a virgin, would you rather sleep with a fellow virgin for your first time or not?

If he already lost his virginity, you can always ask him if he would rather have the opposite option.

40. Would you rather build a good house or buy a Ferrari if you win the lottery?

A house is a more logical option, but a Ferrari would be fun.

Ready, set go! It’s time to play a game of “would you rather” and see if you can learn something about your boyfriend that you didn’t know before. And if you are just playing with a crush, then these questions should help to clue him in that you could be interested in him.


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