10 Wildly Uncomfortable Questions to Ask Your Partner Just for Fun (NOT recommended for new couples…)

Honesty is one thing, but can your relationship handle uncomfortable questions that call for awkward, surprising, or downright brutal honesty?

As you may know, here at Same New Love, we are all about transparency, exploration, and continuous renewal. That often involves asking direct, open, and sometimes even nerve-wracking questions in order to truly learn about each other, confront your differences/insecurities/desires and grow in your relationship that much more.

However, we’ll be honest here… Although the questions in this article may lead to a lot of revealing answers, important discussions, and growth, the real purpose of this article the just to ruffle some feathers and raise discomfort levels juuuust enough to make things interesting (but in a fun, giddy, and humorous way)!

If you’re just starting a relationship (or a situationship) and you’re wondering if it’s even worth it, hold off on these questions and download this date-night question list instead!

Ultimately, we want to make a point that you can be honest about anything – and we mean anything – and still have a loving, secure, and strong relationship.

Now here are 20 questions that might you giggle, shiver, or squirm, but hopefully give you lots to talk and laugh about:

Uncomfortable Questions ABOUT ATTRACTION

1. What would make you less attracted to me? (E.g., cosmetic surgery, weight change, hair change, specific personality trait, specific accent, etc.)

2. What would make you more attracted to me? (E.g., cosmetic surgery, weight change, hair change, specific personality trait, specific accent, a new skill, etc.)

3. If you could change one thing about my current personality, what would it be?

4. If you could change one thing about my current looks, what would it be?

5. What’s the most annoying thing about me?

Uncomfortable Questions ABOUT SEX

6. What’s the kinkiest porn that you watch? 

7. What’s the strangest sex dream you’ve ever had?

8. If I asked you if I could have sex with [insert celebrity crush here], how would you react?

9. Have you ever faked an orgasm with me?

10. Are you satisfied with the size of my penis/breasts/butt/etc.?

11. Do you have a fantasy or kink you’ve been nervous about bringing up with me? If so, what is it?

Uncomfortable Questions ABOUT THE RELATIONSHIP

12. Who has been responsible for most of our fights?

13. What’s the closest you’ve ever gotten to cheating on me?

14. Has there ever been a time you came close to ending our relationship? If so, why?

15. What’s the first thing you’d do if we broke up?

Questions that are JUST PLAIN AWKWARD

16. Which friend of mine do you like the least?

17. Who do you think is my most attractive friend? (personality and/or physical attraction)

18. If you had to choose between me and 1 Million dollars, which would you choose? (2 Mil? 3 Mil? 50 Mil???)

19. What’s your biggest regret in life thus far?

20. Which question made you the most uncomfortable?

If you didn’t fight or get bitter or walk out, then CONGRATS!

On the other hand, if something was a little too uncomfortable, or unexpected insecurities came up – CONGRATS TO YOU TOO!

Identifying insecurities and discomfort with yourself, your partner, and your relationship is the first step on the way to acknowledging, accepting, and working through them. We didn’t want to say this in the beginning and scare you away, but we do think asking each other questions like this is tough at first. But these kinds of silly but awkward questions can build an immense amount of trust, respect, honesty, and, well, humor in the relationship.

Let us know if you agree in the comments. If you hate us now, feel free to let us know that as well. We still love you.

Imani