50 Fun Questions to Ask a Potential Mate to Break the Ice

50 Fun Questions to Ask a Potential Mate to Break the Ice

I’ve been single for a little over a year and a half now. After taking some time to heal and get things back in order, I’ve decided to get a little more social. Lately, I’ve been back on the dating scene trying to keep busy and avoid being socially retarded. I’ve been putting myself in a better position to find good genuine people. Nothing too serious as I believe in a strong foundation of friendship. During this journey, I’ve had a ton of hilarious stories. Let’s just say dating is so exhausting, but fun at the same time!

50 Fun Questions to Ask a Potential Mate to Break the Ice - Natalie Greagor

Someone suggested that I start blogging my experiences. Umm, I passed on this suggestion. In fact, stating anything about my personal dating agenda is usually off limits. But, for the sake of this blog, I wanted to help my sisters and brothers out.


As a lady who enjoys conversation, I’ve realized that some people have a hard time starting or keeping the fire going with a potential mate. It’s not that they aren’t interested/interesting, sometimes (and I say that lightly) they just don’t know what to say. For example, my homies tell me it’s like pulling teeth when they try to get a woman to converse.

Free game ladies: Guys are typically hunters. If you have to chase, most likely, they just aren’t that into you.

Even for myself, I can deal with this truth. Sometimes there is no connection. Also, I’ve hit dead ends with boring guys who want to ask the same questions over and over again, “How are you?” and “What did you eat today?”, with nothing of substance afterwards…”.

Listen, this annoys me to my core. Don’t get me wrong. They are great convo starters, but there’s nothing of substance afterwards. When this happens, I just stop texting or get off the phone.

Anyway, here’s more free game. Here are 50 questions you could ask your potential mate to keep the conversation interesting and moving  (and not all at once to my impatient friends. This isn’t a serious interview.):


  1. If you were forced to move anywhere in the world, accept the country you live in or the country you were born in, where would you go? Why?

  2. Before you die, what’s one thing you want to do, but haven’t done yet?

  3. If I gave you one million dollars today, what would you spend it on?

  4. What’s something you’re great at that not many people know about?

  5. How would your friends describe you?

  6. How would co-workers, peers and colleagues describe you?

  7. What are the top 5 movies you’d watch any day?

  8. Who is your favorite music artist?

  9. What’s one thing (not person) you could never live without?

  10. Would you rather go out or stay in on a Saturday night?

  11. What is your dream car?

  12. What is one guilty pleasure that you enjoy?

  13. What was your childhood like?

  14. What is your biggest achievement to date?

  15. What is your strongest character trait?

  16. What are some flaws you’ve identified and are improving?

  17. What’s the newest thing you’ve tried and hated lately?

  18. What do you love most about traveling/cooking/meeting new people?

  19. What are your feelings towards open relationships?

  20. Have you ever walked away from someone you still loved? If so, what was your mental space after that?

  21. Where’s your safe place or space when the world seems too heavy?

  22. What makes you happy regardless of what’s happening in or around your life?

  23. What is the best advice someone has given you?

  24. What do you like the most about being single?

  25. What do you like the most about being in a relationship?

  26. What is the least rewarding thing about your career?

  27. On a scale of 1 to 5 (5 being extremely important), how important is support of your goals from your significant other?

  28. What are some of your biggest turn offs from a woman/man?

  29. What are some of your biggest turn ons that’s non-physical or sexual about a woman/man?

  30. Regarding finances, who pays the bills or rent? The man or 50/50?

  31. Who was your favorite childhood hero and/or villain growing up? Why?

  32. Are you a risk taker or more calculated?

  33. How would you define happiness?

  34. Who inspires you, dead or alive?

  35. If you could have dinner with only 5 people, dead or alive, who would you eat with?

  36. What do you do to relieve stress?

  37. What was the last book/audiobook you’ve read?

  38. Who’s your best friend and what’s he/she like?

  39. What’s your idea of the best day ever?

  40. What’s something you can talk about for hours?

  41. Do you have any tattoos? If so, where are they/what do they mean and do you want more?

  42. Do you prefer people in your life to be simple, complex or both? Why?

  43. Do you think flirting is harmless or completely disrespectful?

  44. Where would you never ever visit again in your life even if someone paid you? (restaurant, vacation, city, etc)?

  45. What foods do you hate?

  46. What‘s your favorite cooked meal?

  47. If you were on death row and tonight was your last night alive, what meals would you order? But first, what crime(s) did you commit?

  48. Can you tell me two truths and lie and let me guess which one is the lie?

  49. What do you do you after work everyday?

  50. If you ruled the world, what would you change?

50 Fun Questions to Ask a Potential Mate to Break the Ice - Natalie Greagor
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