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[Id and Ego] Getting to Know You: The 15 Best Questions to Really Get to Know Someone

By — One of many Relationships blogs on

While I was researching possible topics for this week, an idea struck me: "Forget about the answers being discovered, look at the questions being asked." For this, I turned to the great internet source of questions - wiki.answers, of course - and while, as you may imagine, there was a lot of wading through questions like "What is the cure for dry heaves?"and "Are the Team Fortress 2 servers down Again?" I.did manage to find a question "gem" that sparked my imagination and reminded me of an interest of mine I had forgotten about.

"What are some good questions to ask to get to know someone really well?"

A little history: I had this journal back in high school I began as a weird sort of project. I brought it with me anytime I thought I might meet someone new, and, most often, that was at The Liquid Room - practically the only place in Grand Rapids a teenager could hang out after dark.

It was this dingy coffeehouse haven for naughty alterna-teens complete with loud rock music, black walls, Christmas lights, beat-up old couches, tv-screens playing obscure black and white movies, and a "Buy one coffee or you're gone you lousy, jobless kid" policy.

In it, away from adult supervision, classmates, and their judgment, we weird kids could be whoever we wanted. Always dramatic, I would hand the journal and a pen, to anyone I found interesting, and with a smile I'd tell them I was collecting souls. ( By this, of course, I meant I was collecting a one page interview with a list of questions I'd concocted (pretty much the same thing!))

They werent great questions. In fact, there were some pretty stupid ones. Still, the journal is now completely full of interviews from random people, some of which I met only once, and others belong to friends I have to this day. It is one of my great treasures.

And to this day, I love to interview people.

I still believe in the power of random, meaningless questions to bring people together, so Im sharing 15 of the best getting-to-know-you questions Ive heard or invented.

Please use them and enjoy!

My 15 Favorite Getting-to-Know-You Questions

In no particular order

1. What are the 5 words that best describe you?

Reveals: This IS sort of a cheater's getting to know you question, but I feel like the list wouldn't be complete without something like it. I like 5 because it's few enough that it forces them to think carefully and be choosy. It is interesting to see if a person decides to use their 5 words on 5 adjectives or to sum themselves up in a 5 word sentence. It's also interesting to see whether they choose all positive words or not.

2. What are your 3 biggest character flaws?

Reveals: I couldn't have the previous question without having a question on flaws. Once again, it's kind of a cheater's question, but if you only have 15 questions to really get to know someone, it seems like a waste to avoid it. What is it that they think is wrong with them? Do they choose to pick flaws that could be perceived as strengths? Does their answer seem genuine or guarded? Do they seem ashamed or proud as they list them?

3. What are you most proud of?

Reveals: This one is mostly getting at the person's values/interests. Do they name an accomplishment, a character trait, a skill?

4. Which character trait is the biggest turn-off for you?

Reveals: Values. What they dislike about others says something about what they value in themselves and the people they care about.

5. What's your favorite movie genre? What are your 3 favorite movies?

Reveals: I'm not the biggest fan of "favorites" questions, but as someone that loves movies, I had to include this one. Besides, despite my "favorites" hang ups, the movie genres people tend to gravitate toward do say something about their personality. Favorite movies say something about a persons taste level and intelligence. "Comedy" people are definitely different than "drama" people. I like three for this because their variety - or lack of variety - alone can be revealing.

6. What do you dream about most often?

Reveals:Challenges. I'm a big believer in the value of interpreting dreams. However, to get to the truth, you may have to dig a bit past the dream interpretations offered in books or websites. Our mind uses symbols we're familiar with and does so in a way that makes sense with our feelings. For example, for a dog lover, a dream dog might symbolize love and friendship, while for someone whos been attacked by a dog, a dream dog might symbolize danger. When we dream, were totally honest and unguarded. Symbols which pop up frequently in our dreams speak to our concerns, challenges, and, ultimately, our heart's desire. Of course, dream interpretation is an inexact science, but people love to talk about their dreams. Why not be the person who gives them permission to do so?

7. What are 5 things you want more of right now? (Could be physical things, characteristics, ideas, anything.)

Reveals: Current struggles, values, and mood. Since I've though this one up, I've made a habit of asking it fairly often just to check in with friends. However, it could work just as well with a stranger.The rule I give, that since I specify "more," they must have some amount of the things they list already. Are there more physical or immaterial things? Are their answers more light-hearted or serious? How creative/personal are their answers?

8. What are 5 things you want to do before you die?

Reveals: Taste, personality, values. Are their answers more accomplishments or experiences? What do they value?

History Questions

9. What's the craziest thing you've ever done?

Reveals: Self-confidence, sense of adventure, and how much they have of each. It takes guts to do something you think others would perceive as abnormal. Is the craziest thing they say theyve ever done really that crazy? Do they seem proud or ashamed of it? Do they, like question 2, seem genuine or guarded in their answer?

10. What's the hardest thing you've ever done?

Reveals: The person's level of life experience, fortitude, as well as what they find personally challenging. Does the hardest thing they've ever done really sound that hard? In what way was it challenging? Mentally? Physically? Emotionally?

11. What music did you listen to in elementary school, middle school, high school and college? What do you listen to now?

Reveals: Okay, as I've said, Im not a big fan of "favorites" questions because, while I think they are interesting, they feel a bit lazy. However, the music you listen to says something about you, and answers to this question reveal both history and character progression. In general, elementary school taste in music has a lot to do with a person's guardians, middle school music has a lot to do with their peers, high school and college has to do with self-exploration, and that's typically when we begin coming into our own. It's interesting to hear what influences a person had in their youth and how much their musical tastes have changed throughout their life. I think that, besides the types and diversity of music they like saying something about their personality, the progression of taste says something about how much self-exploration they've really done.

Hypothetical Questions

12. If you could have any superpower, what power would it be and why?

Reveals: Personality. This question was actually the basis for one of my favorite episodes of "This American Life." Is the power they choose a "showy" power or one they could keep secret? Is their power a common or creative one? Did they choose it for selfish or humanitarian reasons? Maybe its not the most character-revealing question listed here, but it's too much fun not to include. People will love that you asked them.

13. If you could visit any place in the world, where would it be? Would you consider living there?

Reveals: Taste, personality. People who name Paris or Ireland are very different from South Africa or Tibet people. Are they more interested in cities or scenery? Sites or cultures? Relaxation or adventure? Would they consider living in an ideal vacation place? How similar are the characteristics they look for in a good place to settle (logical, practical side) compared with the characteristics of their ideal vacation spot (romantic, idealistic side)? What is their willingness to change?

14. If you could have any job, what would it be and why?

Reveals: Values, interest, and personality. Is their dream job prestigious or low-key? Are they more interested in the money, lifestyle, prestige, or fulfillment associated with it?

15. Would you rather lose all of your memories or never be able to make a new one?

Reveals: Life satisfaction? Willingness to change? It's just a really fascinating question.


Did I forget a really good one?

What's the best question you've ever been asked?



Future Scopes: "The 45 Best Speed Dating Questions You Can Ask on a Prospective Date"

Humor That Works: "50 Questions to Get To Know Someone"

Marc & Angel Hack Life: "50 Questions That Will Free Your Mind" "If You Had 10 Questions to Get to Know Them As Best As You Could, What Would You Ask Them?"

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