40 Funny Questions To Ask Your Friends Or Partner

Here's a list of awkward questions. Avoid them or use them to create embarrassing situations.

Elige entre todas estas preguntas incómodas para usarlas con tu pareja o amigos.
Ask your friends or partner one of these funny questions | Image by Geralt.

There are so many questions out there. We ask most of them to find out who we’re talking to. The problems start when the question is embarrassing for the person that we’re asking it to, or even for both parties.

Maybe the question slips out accidentally and afterward -you realize that it was awkward, or maybe, you did it on purpose to make the other person uncomfortable. In either case, here we have the perfect list of  questions to ask a girl or guy… or not…

40 Funny Questions

Of course, most of these questions would be outright awkward for both parties -so, you should be very confident before you decide to throw them out there.

Usually, the reaction to this kind of question is awkward silence and a “why are you asking me that?” look on the person's face or a nervous laugh, followed by a pause almost more awkward than the question itself. Prepare yourself, because you'll find questions that you can use with your partner as well as friends and acquaintances.

1. Do you really consider yourself a happy person?

A lot of people go around smiling every day, but in reality, they aren’t happy at all. If this person is conscious of their own unhappiness and it’s something that they prefer to avoid talking about, we’re sure that this will create an awkward situation.

2. Who is the person that you have treated worst in your life?

An awkward question for those that are courageous enough to respond sincerely. Maybe some people prefer to avoid reflecting on their actions and convince themselves that they have always been a saint.

3. Have your parents ever caught you masturbating? What happened?

This one’s a classic as far as funny questions go. Asking for them to describe the scene will without a doubt bring the awkwardness to a whole new level.

4. Do you have any embarrassing fears?

There are people out there that are afraid of things that even they find ridiculous, and it’s usually hard for them to admit it.

5. Have you ever declared your love for someone only to get turned down?

This question has an easy response. Most people have been rejected at least once  (or many times). Maybe the embarrassing part of this would be the how and not the yes or no part.

6. Do you have any obsessions or secret habits?

People often carry out fairly “silly” rituals from the perspectives of others. Usually, they are also aware of the fact that these rituals are weird and they are embarrassed to admit it.

7. Are there any lies that you tell about yourself frequently?

Most of the time they’re just small things, but on sometimes, people hide true fears.

8. What body parts do you tend to check out on others first?

If the person you're talking to is liberal, they won't mind telling you what they check out at all. However, if this friend is shy, the question could be very uncomfortable.

9. Is there any part of your body that you’re embarrassed by or that you would change?

This time, depending on who’s being asked the question, it could be awkward. If this person has a fragile self-esteem, responding could be a hard hit.

10. What would you change about your life?

Similar to the question about happiness. Many people feel uncomfortable when they have to admit that they don’t have a perfect life  like they try to make out on Facebook or Instagram.

11. Have you ever been unfaithful?

The numbers are there. A high percentage of the population has cheated at one point or another. The hard part is admitting this.

A lot of people have cheated at some point
A lot of people have cheated at some point


12. Have you ever made a fool of yourself for love?

More than one person out there has ended up begging and pleading for a bit of love from the one they’re head over heels for. In fact, some people are completely blinded by a little bit of affection (or what they see as affection).

13. Are you satisfied with your sexual relations?

Once again, another question that challenges our well-being, but in this case, on a sexual level. To clue you in, most people have had problems in bed  at some point.  The hard part is recognizing this.

14. How many people have you been intimate with?

Many  people will never admit their number. Others even boast about it. However, a lot of people feel really embarrassed when they think that their number is too high or too low.

15. Have you ever thought about having sexual relations with someone of the same sex?

Homosexual fantasies are more common than you’d think among heterosexuals. But, as usual, it’s hard to admit this since it's taboo.

16. Have you ever used an unusual object to masturbate?

From the shower head to some types of food, more people than you would think have used these objects to please themselves. Would you be able to admit it?

17. Will you call me tomorrow?

After a date, this is one of the most embarrassing questions that you can send your date off with, especially if it didn’t go as well as one would wish.

18. Have you ever lied to me?

We all tell white lies -even if it’s just one little comment without any bad intentions. In fact, we’re the ones that lie most to ourselves.

19. Have you ever flirted with a friend’s girlfriend or boyfriend?

This is definitely an awkward question because we know that something really wrong if the answer is ‘yes.’

20. Do you want children?

Depending on how far you are into a relationship and what your level of mutual understanding is like, this question could be uncomfortable. If it is, maybe you should rethink things.

21. Do you want to get married? To whom?

Just like to the previous one. This question could get really awkward depending on the answer or… if the name is someone else’s.

22. Have you thought of getting physical with someone else while we’ve been together?

This is quite normal, especially when the relationship has been ongoing for years. Admitting this shouldn’t be a problem if both parties understand that fantasies or thoughts aren’t equivalent to bad intentions.

23. What is your strangest sexual fantasy?

You’ve got to be careful with this question because a sincere response could surprise and even make the person that you ask it too uncomfortable.

24. Have you ever stalked anyone?

Stalking is something that’s relatively common  especially among young people. Depending on the circumstances, this may or may not be awkward.

25. Why are you with your partner?

If you’re with someone that’s with their partner out of inertia or because they’re dependent on them, it’s possible that this question could generate some awkwardness, because they’ll realize that they don’t many reasons.

26. How much do you weigh?

This is a question that shouldn’t be awkward, but it is still for many people. This is due to society’s pressure for everyone to be at an ‘ideal’ weight.

27. What was your best experience in bed?

Sometimes discussing fulfilling sexual experiences can become quite awkward because it implies uncovering our primitive and liberated side.

28. What was your worst experience in bed?

When things don’t go well, they can be hard to share too -especially if it was our fault.

29. Have you ever slept with a stranger?

This is a practice that’s becoming more and more common and that a lot of people don’t feel very proud of and may even be embarrassed about.

30. If you could do anything, what would you want to do with me right now?

A straightforward question that could end up bringing mutual relief or the end of a friendship. Be careful with how you use it.

31. Have you ever slept with someone out of spite?

More people than you would think, have sexual relations with others just to hurt their exes after a breakup, or when they don’t get what they want. Admitting this after the fact may not be as easy as the action itself, because this implies realizing that we try to hurt others in ways that end up just hurting us.

32. Have you ever had an STI?

This is without a doubt one of the most awkward questions for those have ever had a sexually transmitted infection. Remember to wear a condom.

33. Do you want to meet my parents?

The time comes in every relationship to take this step. For a lot of people relationships with parents are awkward and complicated. Asking this question could give someone goosebumps.

34. Have you ever regretted having sex with anyone?

It’s possible that this person has had sexual relations out of spite or for other reasons that make them feel regret and embarrassment. It could also be the fact that you let yourself “get naked” (physically and or emotionally) in front someone that didn’t treat you right.

35. How long is it?

This is a question that’s aimed at men. Some may take advantage of this to brag about their attributes, but the truth is that most would feel uncomfortable even if they’re happy with their size.

36. Do you watch porn? What kind?

A very direct way to find out about this person’s fantasies. If we follow up this question by asking what kind of porn they’ve downloaded, then it’s the perfect combo.

37. What are your exes like?

Tastes change and sometimes when we look back we realize that we haven’t made the smartest choices in life.

38. How much money do you make?

We shouldn’t be embarrassed to talk about how much money we earn. Because of this, if no one knows how much everyone else is making, the bosses have more freedom to choose their employees’ wages. Remember that someone’s worth isn’t equal to how much money they make.

39. What did you think the first time that you saw me?

Most of the time first impressions have nothing to do with the real person that we have in front of us. Finding out what image that this person had of you at the beginning of your relationship could be equally revealing and awkward.

40. If you could know anything about me or do anything to me, what would it be?

Dare to ask them to express their desires and to get to know you without reservations. After all of this, look at how many questions you already have for him or her.