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21 Deep Questions To Ask Your Partner To Understand Them Better

There comes a time in many relationships where you smugly assume you know everything about your SO. You’ve figured out their pet peeves, you’ve heard that same embarrassing childhood story 10 times, and you can list off all their favorite songs, books, and movies with no effort at all. Trust me, though — there’s still a whole lot you have yet to uncover about each other. Asking your partner deep questions helps you understand them even better than you already do.

It’s really easy to get into a rut with your relationship conversations. “How was your day?” “What do you want to watch tonight?” “Where should we get takeout?” Before you know it, you're asking each other the same questions over and over. Don’t get me wrong — these questions are still essential for day-to-day living. That said, when you get stuck in these routines, you may find you’re not gleaning as much insight about each other.

So, next time you’re snuggling up before you go to sleep, sharing a home-cooked meal, or taking a stroll around your block, consider taking advantage of that time to connect. The best way to do that? By asking some honest, probing questions. Not just any questions, of course — you’ll want to pose the kind that shed light on facets of your partner’s personality you’ve never gotten a glimpse of.

Whether you just started dating someone new and you’re looking to build trust and figure out who they really are, or you’ve been with your current boo long-term and you’re eager to shake your conversations up, these questions are bound to inspire the kinds of talks you cherish forever.

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1. Do you prefer having a plan, or keeping things loose so you can make decisions on the fly?

2. What’s the accomplishment you’re most proud of in your life?

3. Do you think you follow your heart or your head?

4. What’s one thing you’ve learned from our relationship?

5. Did you ever have a goal or dream you didn’t get around to pursuing? What is it?

6. What’s the most challenging obstacle you’ve ever had to overcome?

7. Do you believe that everything happens for a reason, or that everything is random?

8. What does a relationship absolutely need to have for it to be satisfying for you?

9. How do you most like to receive affection?

10. Do you feel you have an easy time forgiving and forgetting, or do you sometimes hold grudges?

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11. What was the last time you remember feeling scared, and what were you afraid of?

12. How did your parents choose your name?

13. If you could go back in time and relive any age, which year would you pick and why?

14. What’s one thing you’re trying to get better at right now?

15. Do you believe honesty is always the best policy, or are white lies sometimes necessary?

16. Do you think you’ve changed at all since we started this relationship? If so, how?

17. How do you like to deal with stress?

18. What was your favorite subject in school growing up?

19. Would you consider yourself a pessimist or an optimist?

20. Would you say you like to take risks, play it safe, or fall somewhere in between?

21. If you could solve one problem in the world right now, what would it be?