Questions to ask your friends

If you want to get to know them better.

"remember when" is the lowest form of conversation.

- Tony Soprano

I think its important when you’re having a dinner party to strive to have “one conversation” at least during the dinner itself. Why get all these beautiful minds together and not focus them like laser beams on a singular point? Besides, its just more fun when everyone is talking and having a lively chat about the same thing. Talking over each other, getting excited, disagreeing, learning, what have you.

The easiest kind of conversation to have is “remember when.” You regale each other with old stories, usually ones half the people have already heard. It’s fun, for sure, but is it getting you anywhere?

If you are curious: I wrote about the types of conversations extensively here.

Where exactly are you trying to get? Closer. The more you get to know your friends the better life is. They become extensions of you. You can climb into their skin and therefore your life becomes bigger. They have experiences and ideas and feelings you have never felt and they can help you to understand them and feel them too. Thats cool and interesting.

Anyways, I’m going to stop waxing away here and get to it. Here is a list of questions to ask the table at dinner parties that spark good conversation and help you know everyone better.

• What’s a mystery in your life you want the answer to?

  • It has to be a mystery that is solvable. So it can’t be like “How would my life have been different if I took a gap year?” it has to be something that someone somewhere knows the answer to like “Why did _____ stop talking to me?”

• If you could have one full time staff member what would they do?

  • Driver, chef, EA, masseuse etc. You only get one. They are on call 24/7.

• If you could retire now and maintain current lifestyle without work but no further, would you?

  • So basically, you’re retired and you receive a paycheck that is exact same as you are currently making for the rest of your life. There is no way for you to make more money than you currently make.

• What is something you love that you wouldn’t recommend to others?

• What’s a lesson you need to keep relearning?

• What’s a piece of advice you give to others but struggle to abide by?

• What’s a small moment from your life that seemed insignificant at the time but you think back on a lot?

• What’s a piece of common advice that you disagree with?

• What’s something that’s farfetched now that you think will be common sense/knowledge in 25 years?

• What thing are we doing today will be most laughed at in ten years?

• What are your arbitrary rules you have for yourself?

  • Things like:

  • I won’t have my phone in bed.

  • I won’t initiate plans with someone more than twice if they don’t initiate with me.

  • I will never ask someone what they do for work.

  • I have to walk 10k steps a day.

• Do you think the goal of travel is to see as many different places as possible or do you prefer to find a place you love and keep going back?

• If you could be an expert in one subject overnight what would it be and why?

• How would you live your life differently if everyone had the same amount of money and there was no way to be poorer and richer than anyone else?

• What thing/trend/practice from the past should we bring back?

• If you could pick one brand and all your stuff had to be from there what would you pick?

• What’s something you were on the wrong side of history on?

• What stereotypes do you think are true?

• What opinions do you have that seem most out of line with your general political affiliations?

Enjoy trying these out! Or don’t, whatever, I’m not the question police. I don’t care what you do.