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50 Deep and Thought-Provoking Questions

Try these ice-breaker questions for a deep conversation with someone else—or yourself!

Try these ice-breaker questions for a deep conversation with someone else—or yourself!

Deep, Thought-Provoking Questions to Get to Know Someone

From time to time I find myself trying to wade through a lull in conversation or trying to find something to get the creative juices flowing. Through all of my experience, the most helpful thing to do in any of these uncomfortable and frustrating situations is to ask a good open-ended question to jumpstart things.

I hope these questions inspire fantastic conversations and help you get to know people on a deep level. I also hope they help you get to know yourself on a deeper level! I've included my answers to the questions below as examples.

1. Who do you most respect at work and why?

A woman named Veronica. She is one of the smartest and most good-natured people I have ever had the privilege of meeting.

2. Who inspires you to be a better person?

My father. If I could be half the person he is, then I know I am doing something right.

3. Who do you depend on the most?

My boyfriend. He has been there for me through everything ever since we were eleven years old. I don’t know what I would do without him.

4. If you could not work for a year, what would you do?

I would finish my novel and self-publish it, along with travel a lot.

5. What's the funniest place you've ever fallen asleep?

In the stands at a Miami Dolphins game!

6. What always makes you laugh?

The movie Christmas Vacation.

7. What one thing would you change about our society?

Social pressures about physical appearance.

8. What do you think about first thing in the morning?

Usually food.

9. If you could have your own TV show, what would it be?

I would want to have my own flats fishing show with Mike.

10. If you had your own TV network, what would you put on it?

I would want something like TLC meets MSNBC meets the Outdoor Network.

11. What or who motivates you to exercise and be healthy?

Being able to have a long, full life for when I have children. I want to be able to play and keep up with them no matter what and be around as long as possible for them. Even though I am not a parent yet, I can't wait to have those experiences.

12. When did your life change for the better?

Taking the job that I have currently, even though I really am not happy with it. Also, I have re-discovered my love for writing again and am making better decisions about my career than I would have never made before.

13. If you could compete in the Olympics, what sport would you choose?

I have always wanted to try bobsledding, so I guess that is what I would pick. It looks so fun and exciting!

14. What is the largest crowd you have ever been in?

I think it might be all of the times that I tailgated while I was in college for UCF football; we always said that we tailgated harder than our team played.

15. What job would you never want?

Hazmat cleanup crew. That job would be horrible for me. I commend the men and women who do it.

16. What's your personal heaven?

My personal heaven would be simple: right next to the ocean with all of my loved ones.

17. When was the last time you climbed a tree?

I was in a park with my dad on a hot summer day right after we just got done with a bike ride. I think I was six or seven years old.

18. Who taught you to cook? And what was the first meal you prepared?

My mom and grandma taught me how to cook. I think the first thing I ever made was chocolate chip cookies from scratch with my grandma.

19. What one question would you ask the President?

I would ask President Obama why he decided to run again after declaring that he would not seek re-election if he did not fulfill his campaign promises during his first term. I feel like he did not fulfill the promises from his first term and should not have run.

20. If you had to live in a small town, which one would you pick and why?

I would pick Vilas, NC. I lived there for a few months one summer and loved how beautiful and peaceful it was. I would move there again if Mike and I could make the same living and be this close to our families

21. What are your parent's best qualities?

Dad: his patience. Mom: her strong will

22. What's your favorite memory of your childhood best friend?

Going to my friend Chelsea's house in Chicago for a week one summer and riding the double decker train.

23. If you could ask one person one question, who would it be, and what would you ask?

I would ask Jimmy Buffett what was his inspiration to start singing because I feel like it takes bravery to go for a dream like that, and I love Jimmy Buffett!

24. What is your favorite movie adaptation of a book?

The Harry Potter Series! I’m a huge Harry Potter fan!

25. What was the first professional sporting event you went to?

A Panthers (Florida Panthers hockey team) game with my dad.

26. What job have you hated the most?

The one that I currently have. I am an executive assistant at a freight forwarding company which actually means I am a curator for my bosses art collection, a billing agent, an assistant to two different people and the receptionist all bundled into one job with little pay. I am taken advantage of constantly.

27. Have you ever performed in front of a crowd? If so, what did you do?

Yes, I was the drummer in an all-girl punk band for two years.

28. Would you rather be wealthy or healthy?

Healthy hands down. I want a quality of life that can only come from being healthy.

29. What's the most comical gift you've ever received?

I got a key chain for Christmas one year from my boyfriend. It's funny in retrospect because of how awful of a gift it was, but at the time I didn't find it funny in the least!

30. How do you manage stress?

I write. I try to get all of the stress, anger, and anxiety out of my body by putting it down on paper. So far, it's helped.

31. What law would you change?

I do not think that marijuana should be illegal in any state for medical reasons. It could be so helpful for so many people.

32. What historical event inspires you the most?

You can learn a lot about a person based on what kinds of events capture their interest.

33. When did you realize you liked/were good at your job?

I do not really enjoy my job. But taking it made me realize that I needed a change in careers. So I guess I learned a lot about myself instead.

34. Who is the best living musician?

My father (he is a professional percussionist).

35. Have you ever had a "now or never" moment?

When I decided to move back home from Orlando, I knew that if I didn’t move when I did that I probably never would. It has been one of the best decisions that I have ever made for myself.

36. What do you want for your children?

When I have children this answer might change, but I think it would be for them to find their real passion in life and see it through, like me with my writing.

37. What is your favorite/least favorite holiday and why?

My favorite holiday is Christmas because of all of the magic that I feel flows through that time of year. I don’t think I have a least-favorite holiday.

38. Can you recite a poem?

I have had "Jabberwocky" committed to memory since the eighth grade when we were assigned to memorize it as a project.

39. What was your favorite summer activity as a kid?

Go horseback riding. I have always loved horses and attended horse camp five summers in a row.

40. Have you ever taken responsibility for someone else’s mistake?

When I was a server, I would take the heat for other servers all the time because I was a “favorite” of my manager and hardly ever got in trouble while other servers would get “punished” for simple mistakes. I also was able to fix most of their mistakes before they could become a problem. I think it was the right thing to do because I was able to help the guests and my coworkers without causing a scene.

41. What's your personal anthem?

The song that defines my life is "Breathe in, Breathe out, Move on" by Jimmy Buffett. I even have the lyrics to one of the verses tattooed on my side:

If a hurricane doesn't leave you dead

It will make you strong

Don't try to explain it just nod your head

Breathe In, Breathe Out, Move On

41. When was the last time you turned your phone off?

Last night, actually. I needed some alone time to reflect on some things that have happened the last few days without distractions.

42. What was your favorite childhood Halloween costume?

Every year I dressed up as a hippie. I always thought that the bright colors and leather vests were awesome.

43. What happy moment will you always remember?

The look on my dad’s face when I came down the stairs in my prom dress.

44. What is one of your PG-rated guilty pleasures in life?

Watching Teen Mom every week with my mother.

45. If you could have any animal as a pet, what would it be?

I would want a tiger, hands down. I would also like to be able to ride it around.

46. What's the greatest invention of your lifetime?

The cellphone. it has changed the world so much in its short time in our lives.

47. What kind of dinosaur would you want to be?

I would want to be a pterodactyl so I could fly.

48. What is your very first memory?

When I was probably two, my mom set me down on the counter to get me a glass of water. While I was there I asked her if I was a big girl. She turned to me, smiling warmly, and said, “You’re mommy’s big girl.”

49. What is one life lesson you will never forget?

I had a teacher, Mr. Grey for third grade. Back then I had a lot of learn disabilities blanketed under dyslexia. My. Grey taught me that even if I learned differently from other children or some things were harder for me, I was just as smart and that I would appreciate my education more. He was so right and I am so lucky that I had him as an educator.

50. What historical figure would you most like to meet?

George Washington.