30 Hypothetical Questions to Ask On A Date That Crush

He's asking some fun hypothetical questions to get to know her better

It’s a great idea to ask funny hypothetical questions on a first date. Good hypothetical questions help to lighten the mood and stop you from taking the date too seriously. A serious vibe only serves to ruin the fun and make you nervous, so it’s better to steer away from that and focus on enjoyable conversations instead.

The great thing about funny hypothetical questions is they also help you get to know each other. That’s what you’re supposed to be doing on a first date, anyway. Better yet, if it’s you asking the questions, it sets the frame of you testing to see if she’s right for you.

That’s a far better frame than trying to prove you’re right for her. If this woman really likes you, she might get a bit nervous thinking of a good answer for you.

In the guide below, there’s a list of 30 hypothetical questions, each with short explanations regarding why they’re good to ask on a first date. So, let’s dive in.

Funny Hypothetical Questions to Ask on a First Date

If you can make a woman laugh, you’ll help her to relax and that’s when attraction can begin to blossom. This list of hypothetical questions should help you to achieve this.

If she gives a serious answer, feel free to throw in a more playful suggestion instead.

1. If you were given the opportunity to live 24 hours as a man, what would you do?

The question is humorous enough, but it gives her the opportunity to give you a sexual answer. After all, most open-minded women would want to do something with their newfound genitals or perhaps experience what it’s like to flirt with women.

2. If you could attempt to eclipse any world record, what would you try to beat?

This is a fun way of discovering what a woman’s biggest hobbies and passions are. Rather than telling you she likes playing the guitar, she can say that she’d like to break the world record for the world’s longest guitar solo.

3. If you could be guaranteed any job in the world, what would it be?

Here’s another example of how exaggeration can create more exciting conversations and more enjoyable dates. Will she want to be the U.S. president or the new host of Saturday Night Live?  Either way, when you ask a woman to imagine any dream scenario, it creates a more positive vibe.

4. If you started a band, what would it be called and why?

Hopefully, she’s smart and playful enough to come up with a fun name based on her personality. Ask what genre of music they’ll play and what instrument she’d play too. This can lead to conversations about her favorite music artists and whether she does actually play any instruments herself.

5. If you were a famous rapper, what would your stage name be and what would you rap about?

This question brings similar vibes to the last one, albeit with an urban twist. Bonus points if she’s willing to spit some freestyle bars for you.

6. If a movie was commissioned about your life, what would it be called and who would play you?

This humorous question can give you plenty of insight into what this woman’s life has been like so far, in her eyes at least.

7. If you had to get a tattoo on your arm tomorrow, what would you get?

Another interesting and potentially amusing way of finding out what really makes this woman excited in life. It’s a great hypothetical question to ask if she has some little tattoos and is interested in getting more.

8. If you had to watch one movie on repeat for the rest of your life, what would it be?

This is a fun spin on the over-used getting-to-know-you question of “what’s your favorite movie?” Now, this woman has to consider whether it’s a smart idea to watch an action film or a horror movie endlessly until she dies. Surely a comedy or a romance might be more bearable?

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9. Would you rather be bald forever or never be able to cut your hair again?

“Would you rather” questions with two options are a commonly-used form of hypothetical question. This one will tell you about the importance of traditional beauty to her.

10. If the police stuck a warning sign on your back, what would it say?

Essentially, you’re asking to list her biggest flaw, but with this fun exaggeration attached to it. Perhaps it’s not a sign, but a red flag 😉

You can typically use exaggeration to add humor to any simple getting-to-know-you question - and this police sign question is no different.

Hypothetical Scenario Questions to Ask for Fun

The great thing about hypothetical scenario questions is that it’s easy to give them sexual or flirtatious connotations, as you’ll see from some of the suggestions below.

11. If you could date any celebrity, who would you choose?

This will give you a nice idea of her ideal “type”. Does she like tall rugged action heroes or the pretty-boy pop-star type? You’re about to find out…

12. If your celebrity crush walked in here right now, what would you do?

This is a chance for her to show you how good (or not so good) her flirting skills are. A nice question to ask if she doesn’t appear to be flirting with you at all yet.

13. If we could go on a date in any city in the world, where would you want to go?

This question will send her imagination running wild, and you’ll be able to find out what type of dates are her favorite. The cheeky thing is: if you can help roleplay about what you’d do on that date, it’ll feel a little bit like you actually took her there.

14. If you were gifted $5,000 but only had 24 hours to spend it, what would you buy?

You can learn about a woman by giving her a hypothetical blank cheque. Is she going the basic route by buying clothes, jewelry or handbags? Or does she have more original goals for her life? Once again, this question is sending her into a fun fantasy world, which can help her relax and enjoy herself.

15. If you knew you had 10 days left to live, how would you spend it?

This is more of a morbid fantasy world, but it gets her thinking about taking spontaneous actions and how life can be so short. This can be a good mindset if you’re trying to take her home that night.

16. If you could choose what animal to be incarnated as, what animal would you choose?

A more fun version of the classic “what is your favorite animal?” question. Now, she’ll have to consider what day-to-day life would be like as that animal.

17. If your crush was too shy to ask you out, would you ask him?

This is an interesting question because it highlights that you were brave enough to ask her out. (Bonus points if you did it in real life, rather than via a dating app).

18. Would you date a guy who was really shy if he was also really good-looking?

This is a not-so-subtle way if she thinks looks or personality are more important. Hopefully, it also helps remind her that you’re not shy and that’s why she likes you.

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19. If we were to have kids, do you think they would be cute?

A more flirtatious fun question that allows her to future-fantasize about starting a family. It’s probably best to wait until she’s complimented your looks to ask this question. If you want to know the answer to this question, there are actually apps that will predict what your kids will look like based on your selfies.

20. If you had to give up alcohol or sex for one year, which would you give up?

You can replace alcohol with anything else that she’s said she enjoys. Either way, if she chooses to ditch the alternative to sex, you’re on the right track. Until they get comfortable around you, most women will play the role of an innocent princess who doesn’t even like sex that much.

What Would You Do Scenarios to Talk About with a Girl

When you create fictional “what would you do” scenarios, it makes a woman think on her feet and gives you interesting insights into her personality. Here are some examples of great ‘what would you do’ scenarios:

21. What would you do with three wishes from a magic lamp?

Is she going to solve world hunger or fulfill her selfish desires? To make this question more flirtatious, remind her that (according to the film Aladdin) she can’t make anyone fall in love with her or kill anyone.

22. What would you do if you were given the opportunity to live one day all over again?

It’s one of those hypothetical questions that bring on nostalgia. Essentially, you’re asking her what’s the best day of her life, but in a more fun way that encourages her to relive it in her mind. Hopefully, she doesn’t choose an awful day that she regrets and would like to redo. That could murder the vibe.

23. What would you do if you had to choose between your best friend or your Instagram account?

She has to lose one forever. What would she choose? A particularly pertinent question for a woman with loads of followers and pictures on her profile.

24. What would you do if your boyfriend gained 100 pounds overnight?

Would she stay with him? Would she help him lose weight? Or would she ditch him for a more aesthetically-pleasing partner? Another scenario that tests how superficial she is.

25. What would you do if you had an opportunity to send an SMS to every phone number in the world?

An opportunity to get deep. What message does this entire world need to hear?

26. What would you do if your true love cheated on you? Would there be any way back for him?

How is her attitude to infidelity? How open-minded is she to this sort of thing happening? This can lead to questions of whether she’s been cheated on, or whether she’s cheated on someone else. It’s typically only people who have cheated themselves who would consider forgiving a cheater.

27. What would you do if we were locked in this venue alone for 24 hours? Would we enjoy it or drive each other crazy?

Another hypothetical scenario that tests how much she likes you. This question is more fun if you’re at an interesting date venue, like an amusement park or a zoo.

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28. What would you do if you had the magical power to seduce anyone? Would you use them?

It would be tempting to use these powers whenever you see someone you’re attracted to. But maybe she wants someone who chooses to love her for who she actually is.

29. What would you do if you were invisible for a day?

Another perfectly innocent question which she could turn sexual if she was in that sort of mood. After all, a lot of people would surely opt to sneak up on their crush in the shower.

30. What would you do if I kissed you right now?

Ok, this might seem a bit cheesy. But, if you’re seeing signs she wants to be kissed, this might be a smooth way to transition from hypothetical questions to making out.


That’s your list of hypothetical questions to ask a woman. The great thing is: you can throw these questions into the conversation whenever you want. Because they’re hypothetical, they’ll never run out. So, if you’re worried about running out of things to talk about on a first date, you can have a few of these questions prepared.

There’ll be no reason for an awkward silence ever again, plus you’ll be able to learn some cool stuff about how your date’s mind works.

For more ideas to ensure your first dates go really well, check out this list of expert first date tips.

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