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Fun Things To Ask Him When You Play ‘20 Questions Game ’

Isheeta Sharma | May 18, 2022

For those who don’t know, ‘20 Questions’ is a fun game you can play with your boyfriend! The basic idea is that your partner thinks of a place/ object/ person and you have to guess that in 20 questions or less with him answering in just ‘yes’ or ‘no’.

20 Questions Games To Ask a Guy or Your Boyfriend

However, with time, there have been several variations to the game and, since we can’t read your boyfriend’s mind, we bring you one such variation. We have a list of 20 questions that he can answer in either ‘yes’, ‘no’ or single word answers. No asking for details, ladies! This will help you two get to know each other better, so get ready for an interesting session of a twenty questions game with your S.O.!

20 Questions Games To Ask a Guy or Your Boyfriend

Be it flirty or entirely playful, we bring you 20 questions ideas that will fit your every mood!

1. What do you prefer – ordering in or eating out?

A very important question to ask if you see a future with the guy. After all, you don’t want to be fighting over where to eat every day, right?

Also read: interesting questions to ask your crush

2. Do you check me out when I walk away?

This is something sweet and sexy that guys do that will give you an instant confidence boost. To know that someone looks at you the way the hero looks at the heroine in a movie when she is walking away… Wow! This will also give him an insight on how to play 20 questions!

Also Read: Couples drinking games ideas

3. Have you ever been suspended from school?

It shouldn’t all be related to your relationship. If you really want to get to know the guy then you should also know about his life before you, right?

Also Read 52 Dumb Charades Movies That’ll Always Ensure You Win!

4. What’s your favourite part of a girl’s body?

One of the very sultry of our 20 questions ideas, make sure that you make the most of it! Also, ensure he names only one! Anyway, this is just FYI. Well, it doesn’t hurt to know, right?

Also read: Truth and dare question to ask your boyfriend

5. Are you a superstitious person?

His beliefs or the lack of them for that matter won’t seem to matter right now but eventually, they will seep into your relationship. It’s better to know beforehand what you are getting yourself into.

Also Read: Dirty this or that questions

6. Do you like talking dirty?

Chances are he’ll say that, of course, he does. But it’s always better to confirm anyway!

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7. Have you ever thought about marriage seriously?

Yes, it might be too early in your relationship to be talking about marriage but this question talks about marriage in general. Has he ever considered it? Does he believe in it? His one-word answer would be enough to know, definitely one of our best 20 questions ideas if you’re looking for some serious answers!

8. Has anyone ever accidentally seen you naked?

It would make for a great story to hear later on if he says ‘yes’, won’t it?

9. Do you like waking up early or staying up late?

There are two kinds of people in the world – the ones who wake up early and the ones who stay up late. They both get to see the morning light but in completely different ways. Don’t judge him on his answer but you should know if you are a similar kind of love or the opposite kind of love.

10. Have you ever had a sex dream about me?

Guys do have sex dreams about their girlfriends but they don’t like to admit it in order to not freak her out or make her feel weird about it. However, you asking him would be reason enough for him to tell the truth and definitely something you would be interested in knowing.

11. Do you see children in your future?

Again, a heavy question so doesn’t judge him on the answer. Even if he says ‘no’, it doesn’t mean he will never have children in the future. It’s just something to help you figure out whether you are on the same page as him yet or not.

12. Do you enjoy phone sex?

Because if you guys go far and long, someday or the other you will try phone sex…or not, depending on his answer! This is anyway a great initiation when it comes to how to play 20 questions with a guy.

13. Do you sleep in pajamas, underwear or nothing at all?

Want to play 20 questions with your guy but don’t have a clue how to begin? Well, you can definitely use this one to make things easier for you when you are thinking about him at night! *Wink*

14. Have you ever sent a nude picture?

You should ask him the question to up the fun in the game but don’t jump to the ‘to whom’ question soon after it. Whatever happened in the past is already gone so no need to worry about it. But you can still tease him about it a bit!

15. Have you ever been dumped?

Honestly, if you can get a guy to trust you and open up his heart to you about things as sensitive as this then you can get him to trust you with anything!

16. Do you think you are a good kisser?

Let’s find out his level of narcissism, eh? And later, you can even test his abilities! We know you want to! One of the best 20 questions ideas out there to get things started on a great note.

17. What is more important to you – truth or happiness?

This questions will really define the kind of man he is. Does he embrace happiness or truth and how does he deal with both? But before you go asking him this, maybe it isn’t a bad idea to ask yourself too. Some food for thought, eh?

18. Have you ever been caught while in action?

Get to know all his naughty secrets so that you can pull his leg about it later on! Definitely one of the must-have 20 questions that should be on your list!

19. Do you like pets?

This will help you know what the future would look like. Yes, the one you can already see in your mind.

20. Do you like using props in the bedroom?

Just to keep in mind when you decide to go a little out of your comfort zone in the bedroom! This will really give you a better idea about if he’s willing to experiment in bed or not.

21. ‘Have you ever woken up with someone and been confused about it’

There are times when one can’t help being confused and surprised by all the little things life throws at you. Always better to know what’s been up in his mind, isn’t it? However, don’t go ahead and start judging him for it!

22. ‘Are you up for commitment?’

Nothing could possibly be a better way to ask him about this question. However, save your whats and whys for later!

23. ‘Are you a mountain person or a beach person?’

It never hurts to know which one your boyfriend prefers, and it will also come in handy just in case you’re planning your vacation!

24. ‘Beer, gin, vodka, or whisky?’

Know his poison and then get to know him! Always great if you know his preferences on the off-chance you think of throwing him a party. Trust us, he’ll be pleasantly surprised!

25. ‘Do you prefer dogs or cats?’

For this as important as preferring tea or coffee! And if you’re planning on moving in with him and prefer some furry pals of your own, it never hurts to know whether he’s looking forward to having some furry friends or not!

26. ‘Coffee over tea, or tea over coffee?’

Which brings us to our next question, for you need to know if you’re with a coffee or tea person! You can figure out whether he makes great tea or coffee later!

27. ‘Do you prefer chilling at home or partying outdoors?’

For this is going to decide most of your evenings should the two of you actually end up together! And it will help you plan out how you can spend your next weekend the next time you happen to meet each other.

28. ‘Game of Thrones or Harry Potter?’

Knowing your fandom is important, and liking both works too! The two of you can also sport matching merchandise, it would look super cute!

29. ‘Marvel or DC?’

It’s time you knew about where his allegiance lies! And if the two of you happen to support different comic universes, then it’s going to be one fun battle between the two of you!

30. ‘Which do you fancy more? Boobs or butt?’

For you know men always have a tendency to prefer one over the other! 😉

31. ‘Do you prefer texts or calls?’

So you know whether to call or text him the next time you feel supremely overwhelmed! And maybe let him know whether you’re a text or call the person as well?

32. ‘Would you kiss me in public?’

A simple ‘yes’ or ‘no’ will be enough to satiate your curiosity, so stash this in your list of 20 questions ideas!

33. ‘Where is your favourite place to be kissed?’

Because you can’t wait to explore him further for you next date night together! 😉

34. ‘Have you ever been cheated on?’

While you don’t have to necessarily have to dig in the past, knowing what happened helps to understand what might trigger him, and to steer clear of things that might potentially upset him.

35. ‘Have you ever watched porn with someone else?’

Remember, you’re only asking him in the spirit of the game, so don’t follow up with questions later! Because some questions are better left unanswered.

36. ‘Have you ever written a love poem for someone?’

You would get to know whether he has that side of a hopeless romantic in him, and one of the sweetest 20 questions ideas to ever exist!

37. ‘Have you ever dumped someone over text?’

And a little something to know about his more rougher edges! But, like everything tricky, don’t judge him before you get to know his reasons, and store your questions for later.

38. ‘Have you ever made breakfast in bed for someone?’

There’s no harm in knowing whether he’s done all those lovey-dovey things for someone or not! But don’t go ahead expecting him to do the same for you, because maybe he just might not be into it anymore.

39. ‘Have you ever hooked up with a complete stranger?’

Remember, it’s entirely okay if he says yes. You just have to figure out whether you can make peace with that! And there’s nothing wrong with him having fun every once in a while as long as he’s single.

40. ‘Have you ever gone on a date with a friend?’

Keep further questions at bay, because you don’t want to turn a fun game into something which becomes an awkward conversation for the two of you!

We hope these questions will give you a lot of scope to get to know your guy a bit better!

GIFs: Giphy, Tumblr

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