A Massively Underrated Writing Prompt and Exercise: Personal Letters to Friends

The most prolific writing period ever in my life was during senior year of high school. Instead of following the classic tradition of writing in people’s yearbooks, I wrote letters to give my friends and peers, some spanning multiple pages and thousands of words long. I wrote letters to over 50 friends, each one being at least a full page long (12 point font, no double-space).

From both angles of substance and style, I fearlessly swung for the fences. I described the people I admired in the best light possible, addressing everything from their fashion sense to their physical and verbal mannerisms. I detailed what I respected about their interests and talents, recounting stories I remembered most fondly whether small moments in class while sitting across from them and working on group projects or big, grand moments on stage and at football games.

I was open, expressive, and honest. I trained talking in tangibles and crafted scenes in the concrete. It was an exercise in creative writing, storytelling, and vulnerability.

It’s been a practice, ritual, and gift I’ve tried to give myself and those I care about ever since. It’s probably one of the best birthday gifts I or you can ever give. I may not always know what the perfect gift is to buy, but I am always willing to challenge myself to say what I think captures how I feel about and see someone.

Why You Should Write Letters Too

I recommend it for anyone who writes because it will be more practice in writing and because of what feels the psychological benefits. Here are some of them:

  • It’s far easier to get into a flow state because you know your audience and your message.
  • Tip: outlining still helps and so does applying story structures and creative writing elements.
  • You are channeling feelings of gratitude, admiration, positive reminiscence. It’s comparable to a variation of loving-kindness meditation.
  • You may even open yourself up to reflecting on and working through more difficult parts of your past while remembering and acknowledge the people who helped you through them.
  • Your reader will appreciate that you thoughtfully hand-crafted something tailor-made and just for them.
  • You’ll get some writing done.
  • It might be bad, but it’s usually not. However, the intention will always be right and the effort justified if it’s from a place of love.

If you’re experiencing writer’s block or want to spend a quiet evening writing but are intimidated by larger creative ambitions, try writing a letter. Focus on one reader and one page. Trying just this might help get the momentum going.

It’s also never a bad idea to say thank you. When’s the last time you did so?



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Jason Lam

Jason Lam

Head of Admissions Consulting | Point Avenue