10 Prompts for Writing Letters to Friends and Overcome Writer’s Block

No matter how insurmountable writer’s block may seem, I have always found that the least I could write is a thoughtful letter to someone I care about.

While there is still sometimes the pressure to write something well-written, to craft a letter that deeply moves them, the intention is rarely ever a waste or a mistake.

No matter how incapable I may feel of generating ideas for writing, there are a vast number of individuals in my life I can choose from that lends a specificity of focus to facilitate idea generation.

And to facilitate ideation and content generation further, it helps to have prompts that guide your thinking and ideating through questions.

Prompts to Help You Reflect On and Appreciate Your Relationship and Move the Recipient

  1. The top X things I admire most about you
  2. My favorite X memories I reminisce about when I think of you
  3. The X most significant lessons you have taught me
  4. What I wish I could model after you
  5. X moments between us you probably never knew I think about all the time
  6. X things I hope we end up doing together in the future
  7. X achievements and actions of yours that changed me for the better
  8. X things that you said to me which helped me become a better person
  9. X goals and pursuits I hope you eventually achieve in your life
  10. X ways you have impacted my growth, happiness, and success

The Benefits of Writing Letters to People You Care About

If you are struggling to maintain a daily writing habit, trying applying any of the above prompts to anyone whom you would want to answer that prompt for. If your goal is to practice your creative writing abilities, try to apply as many storytelling and creative writing elements to your letter.

Beyond being meditative deep work which produces a variety of benefits in one’s thinking and emotional and mental well-being, writing such letters is a low cost hobby that harms nobody. Meanwhile it helps facilitate the process of practicing the craft of writing by providing a positive purpose.

I’ve spent afternoons writing letters, as well as flights and late nights. And each time there are a multitude ways of I can modify it as a practice and exercise — word limits, page limits, experimenting with structure, deliberately practicing specific creative writing elements (narration perspective, dialogue, imagery, etc.).

If you have been meaning to write and have struggled to embrace the fear that has been holding you back from trusting yourself to figure out how to succeed on your own terms, try writing letters.

You have nothing to lose, and maybe almost everything to gain.



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Jason Lam

Jason Lam

Head of Admissions Consulting | Point Avenue