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You are finally home for the holidays! Getting all cozy in your PJs, eating whatever you want to, catching up on all the TV you missed. Then you hear from the other room, “So, how…what did you do last semester?” EEK. Nope. Can’t deal with that conversation.

You will be home for the next month, and most of your fun stories are tenuous at best. You know you need to talk to your Mom about something other than going over the family activities you’ll be doing on Christmas Eve or asking about all of your relatives, again. 

I’ve always loved talking to my parents and have been lucky enough for them to be pretty open-hearted when sharing stories, but even our conversations die out sometimes. In light of this, I decided to create a list of questions that I’ve categorized into light and engaging, long-form answers, dinner conversation, and heart-to-heart. You’re welcome. 

Light and Engaging

  • Any advice for getting a job?
  • What was your fondest memory from college?
  • Any horror stories from your first job?
  • Do you know any gossips at work/life? 
  • What sickness did you lie about to get out of work?
  • What is the biggest compliment you have received?
  • If you had a brainwashing machine, who would you use it on?
  • What is the strangest name you’ve been introduced to?
  • What type of music do you listen to?
  • Have you ever been pulled over by a cop?
  • What famous person do people tell you you resemble?
  • Which of the four seasons do you like most?
  • What did you do earlier today that you are/were most excited about?
  • What is your favorite movie?
  • What’s the story about the last picture you took on your phone?

Long-Form Answers

  • What was the biggest lesson from your 20s?
  • What accomplishment are you most proud of? Why?
  • What do you wish you spent more time nurturing in yourself?
  • What do you want to spend less time doing?
  • Describe something utterly unexplainable that has happened to you? Paranormal, dumb luck, meeting a person?
  • What was your life like at my age?
  • What do you miss most about your childhood?
  • Have you ever been stung by a bee? Or attacked by an animal?
  • What habit are you proudest of breaking and why
  • What is the strangest thing you have ever eaten?
  • Is there something you feel like you are constantly losing around the house?
  • What dead person would you most and least like to be haunted by?
  • What is your dream vacation? Or best vacation?
  • What do you want to do for your next birthday?
  • What question do you hate to answer?
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Dinner Conversation

  • If you could plan a heist, what would you steal, and what characters would be on your team?
  • Do you know your heritage?
  • What would you choose to see if you could have witnessed any time/event in history?
  • If you could wake up in someone else’s body tomorrow, who would you pick, and what would you do?
  • Would you eat a bowl of crickets for $40,000?
  • If you could be any age for a week, what age would you be?
  • What have you always wanted? Did you ever get it?
  • What was the weirdest prank call you ever made?
  • Do you have a favorite book?
  • What is your favorite knock-knock joke?
  • If you could retire tomorrow, what would you do?
  • Airplane, train, car, boat, subway, or teleportation device? 
  • If you could be trapped in a TV show for a month, where would you go?
  • What’s the longest you’ve gone without sleep?
  • What’s the strangest thing you have eaten?


  • What is your greatest strength or weakness?
  • What cheers you up?
  • Who is your hero?
  • What do you think is the most unique thing about you? Do you like it? 
  • When you picture my future, what do you see for me?
  • What have you always wanted to tell me? 
  • Do you get along with your family? Why or why not?
  • When did you know you were in love?
  • What have you always wanted to ask me?
  • What is the most terrifying moment of your life so far? Have you recovered from it?
  • Do you have anyone you go to for advice? 
  • What does contentment feel like to you?
  • Is there anything I should know?
  • What do you think about constantly that makes you sad or happy?
  • What is your absolute, lifelong, favorite song/story/ memory?

I hope these helped spark some great conversation between you and your chosen families this holiday season. Connecting with people is, at its core, what the holidays are about. I know this time of year is a contentious time for some, and I know I am privileged with my family. These conversation topics have always made me feel grounded, supported, and excited to get to know my own answers. These questions are truly meant to be universal topics you could ask your friends, counselors, cousins. Get in touch with yourself and the people around you this holiday season. If you find yourself drawing close to a subject you like, check out Upkey’s Job portal for more ways to explore an internship or job opportunity! Before applying, tighten up your resume with our Resume Scorer. 

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