Search page
Open menu

20 Questions To Ask *Him* When You Play ‘20 Questions’

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’. 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.!

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 everyday, right?

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!

2 twenty questions game

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?

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


Make sure he names only one! Anyway, this is just FYI. Well, it doesn’t hurt to know, right?

4 twenty questions game

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.

6. Do you like talking dirty?


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

6 twenty questions game

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.

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?

8 twenty questions game

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 the 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.

10 twenty questions game

11. Do you see children in your future?


Again, a heavy question so don’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, some day or the other you will try phone sex...or not, depending on his answer!

12 twenty questions game

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


Just 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!

14 twenty questions game

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!

16 twenty questions game

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!

18 twenty questions game

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.

20 twenty questions game

GIFs: Giphy, Tumblr
Published on Nov 09, 2016
POPxo uses cookies to ensure you get the best experience on our website More info
Never miss a heart!

Set up push notifications so you know when you have new likes, answers, comments ... and much more!

We'll also send you the funniest, cutest things on POPxo each day!