One-to-one time between Bigs and Littles is what Big Brothers Big Sisters is all about. That time together is fun, meaningful, and it strengthens relationships. Here's a list we've compiled of great things to do one-to-one with your Little.


Some matches are now meeting in-person in compliance with social distancing guidelines, while others may choose to remain meeting virtually. Whether your next chat with your Little happens during a walk around the block or via a FaceTime call, these ideas might help spark some fun & worthwhile conversations.

20 Questions

  1. Who is your hero?
  2. If you could live anywhere, where would it be?
  3. What is your biggest fear?
  4. Where is the best place you have ever been?
  5. What would you change about yourself if you could?
  6. What really makes you angry?
  7. What motivates you to work hard?
  8. What are you most proud of?
  9. What makes you laugh the most?
  10. If you could choose to do anything for a day, what would it be?
  11. If you could only eat one meal for the rest of your life, what would it be?
  12. What is your favorite holiday and why?
  13. If you were stranded on a deserted island and could only have 3 things, what would they be? (no electronics!)
  14. If you could buy anything in the world what would you buy?
  15. If you could visit anywhere in the world where you go?
  16. If you owned a restaurant, what kind of food would you serve?
  17. What are you most thankful for?
  18. If you could have everyone in the world follow one rule for an entire day, what would you want people to do?
  19. If you were a color, what color would you be?
  20. What is your favorite thing about you?

This or That?

  1. Visit the beach or mountains?
  2. Be a wizard or a ninja?
  3. Plant trees or clean up the ocean?
  4. Early Riser or Night Owl?
  5. Meet a talking giraffe or dolphin?
  6. Live in a teacup or underneath a mushroom?
  7. Be an Olympic Athlete or President of the United States?
  8. Have math homework or reading homework?
  9. Invisibility powers or ability to fly?
  10. Sweet candy or sour candy?
  11. Hot dog or hamburger?
  12. Play sports or make crafts?
  13. Movies or TV Shows?
  14. Talk to animals or read minds?
  15. Broccoli or brussel sprouts?
  16. Rollercoaster or Tilt-a-Whirl?
  17. Eat hot salad or cold soup?
  18. Have a magic carpet or a personal robot?
  19. Christmas or Halloween?
  20. Have one eye or two noses?

Gratitude Scavenger Hunt

  • Something that makes you smile
  • Something that is your favorite color
  • Name 3 people you are grateful for
  • Something that makes you laugh
  • Play a song that makes you happy
  • Something special to you
  • Something unique
  • Something that makes you feel loved

Mental Health Check-in

Over the past couple months, we have all learned so much about the importance of taking care of ourselves. Chat with your Little about the different things they do each day to make themselves happy! Here are some other questions you could ask them to get the conversation started:

  • What are you looking forward to this summer?
  • What do you dream about?
  • What things do you worry the most about?
  • What is the best part about being home?
  • Is there anything you don’t like about being home?
  • What is one of your future goals?

Just a reminder that if your Little ever shares anything that is worrisome to you, please be in contact with your Match Support Specialist.