Abolitionist Mail Project
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​Icebreakers/prompts for penpal pairs

A blank white piece of paper can be intimidating. Maybe you can’t think of what to say. Maybe there’s so much you don’t know how to start. We hope you and your pen-pal can use these prompts to get to know one another better. Here's a printable version to share with your pen-pal.

How to use icebreakers
  • We suggest answering one or two prompts at a time so that you can answer in detail
  • Explaining your answer is half the fun! Try to write at least 5 sentences so your pen-pal can learn more about you.
  • Take your time answering and tell a story or show more about yourself.
  • If a prompt isn’t interesting to you, that’s okay. You could pick a few keywords from the prompt and talk about something related to them, or ask a question and answer it yourself.

​Talk to me about… 
  • If you had to live in a sitcom universe for a year, which show would you choose and why?
  • What’s a song lyric or quote you really like? What does it mean to you?
  • When is a time you felt proud of yourself? Please brag!
  • What are some of your values (things that you believe are important in the way you live and work)? How do you practice them?
  • Are you an artist or lover of art? If, so what kind of art speaks to you? How do you define yourself as an artist? What materials do you use to make your art on the inside and outside?
  • When was the last time you danced? What song did you dance to?
  • If someone visits your hometown (or another place you know well), what should they check out? Help us imagine the location.
  • Draw a self portrait to share with your pen pal. It doesn't have to be realistic or perfect. You can collage, draw, paint, add words, images, etc. to showcase your personality and what makes you unique!
  • What food would you like to eat every day? What is a memory connected to that food?
  • If we make you sing karaoke, what song would you sing? Why that song?
  • If you were an action figure, what would your accessory be? Would you have a super power?
  • Tell me about a role model in your life who means the most to you. Why was their mentorship so important to you? How do you mentor others in your life?
  • If you were in a cartoon or comic, what outfit would you want to wear? Draw it!
  • Who's your favorite public figure and why? If you were a public figure, what would you like to be known for?
  • What do you freedom dream about? What makes you feel free?
  • What's your favorite time of the year? Which season do you look forward to most? Do you have a favorite holiday? Why do you like it?
  • Write a short poem, song, or fictional story to share with your pen pal. Be as detailed and as creative as you'd like. If desired, invite your pen pal to continue writing something together or to share an original writing of their own.
  • Tell me about a time when someone changed your mind about something. How did they change your mind?
  • Pick a color that best represents you. Why that color? What does that color mean to you?
  • If you could shapeshift into one animal on earth, which one would you choose and why? What would you do on your first day in this animal form?
  • Imagine that you're an inventor with all the resources you need to build something brand new. What would you create and why?
  • Are you into politics? Would you consider yourself politically active or civically engaged? Why or why not?
  • Tell me about a time when you laughed so hard you cried. Try to make me laugh too.
  • Trace your hand. Send it to your pen-pal and have them trace theirs over it. Send it back. Each of you can keep a copy. Even though your hands don’t get to touch the same paper, you can look at the outline and know your friend is with you.
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  • About us
    • About AMP
    • Mission and Values
    • Contact
  • Connect inside
    • Ways to connect >
      • Mail, phone, and more
      • How to use Corrlinks
      • Icebreakers
    • Card crew
    • Inside/outside reading group
    • Pen-pals >
      • About pen-pals
      • Find a pen-pal in Massachusetts
  • Events
    • Events calendar
    • Somerville card parties
  • Sign up
    • Write or organize with us
    • Incarcerated member sign up