How to stay in touch—4 steps to being a prolific pen pal

Published: Mar 22, 2024

A woman sorts through many postage stamps for her pen pal hobby
Caesar sorts through her many dozens of stamp options. (Marlayna Demond '11/UMBC)
a headshot of a woman in a floral dress standing with her hands folded in front of letter writing paraphernalia
Headshot of Winona Caesar ’09 in her letter writing “command station.” (Marlayna Demond ’11/UMBC)

With Winona Caesar ’09, American studies and history

As a first-year student—before classes had even started—Winona Caesar ’09, American studies and history, took to heart some advice she heard at Welcome Week: Keep in touch with your loved ones. So she started writing to her grandfather who lived a few miles down the road in Baltimore City. And then, two years into their correspondence, he passed away. “His letters were amazing,” says Caesar, “a wealth of knowledge.” 

Around that same time—halfway through her time at UMBC—Caesar’s older friends began graduating and moving around the country. She kept in touch with a few of them through letters, occasionally splurging on stickers to be extra thoughtful. Now she spends a good portion of her free time corresponding regularly with 16 established pen pals, although she’s written back and forth with more than 50 interlocutors in the past two decades.

For Caesar, a sergeant in the Baltimore City Police, it’s a creative outlet. Whether hand writing a letter or using one of her seven typewriters, Caesar says the process slows her down and connects her to individuals all over the globe. As the world grows increasingly more digitized, Caesar and her pen pals are saving the lost art of keeping in touch.

Tools of the Trade:
A writing implement
Paper or postcard
Postage stamp
Envelope (handmade, if you’re serious about this)
A collection of stickers or ephemera to share

a photo of a series of photo booth pictures of two women

Step 1: Find a willing pen pal (or several)

For Caesar, her letter writing career started as a natural offshoot of keeping in touch with loved ones, but she has since joined two professional letter writing societies that connect new pen pals and charge a very small fee to screen participants.

Caesar says that not all matches work out but letter exchanges that hit a good groove sometimes go on indefinitely. One of her first matches was with Amy in Tennessee [pictured in the photobooth series with Caesar, left]. After seven years of corresponding, while on vacation in Tennessee, Caesar and Amy met up. Caesar says her pen pal was exactly like her letter-writing persona. “Reading her writing and meeting her in person, it was like we were best of friends. It worked,” says Caesar.

Step 2: Tap into your creativity

Caesar has been writing and sending letters long enough that she can hand make an envelope with her eyes closed, she says. In her writing nook in her apartment, Caesar keeps clear boxes stacked on each other—each organized by the correspondent’s name and send date—with thousands of letters filed inside. Nearby are her collection of typewriters, her stash of pens, her paper supplies, her stamp options, colorful washi tape, old magazines and paper samples for envelopes, so many stickers and other fun items to include in her letters. 

Seated in a command-center-like swivel chair in the middle of her supplies and the sun streaming past her collection of succulents on the window nearby, Caesar will spend as long as she needs to (and as much energy as her job leaves her) replying to friends and new acquaintances near and far. 

a box full of colorful envelopes
A small section of the many thousands of letters Caesar has filed away from her pen pals. (Marlayna Demond ’11/UMBC)

She says she doesn’t plan out her responses in advance. “I try to react directly to the letter and then add any extra stuff that’s coming up in my life, like, ‘Oh, I got a future trip,’ or ‘This is how I’m feeling.’” With some correspondents, she plays on-going games of hangman, scavenger hunts, mystery games, or Pictionary.

Step 3: Share as much as you want about yourself

a small bear sits on a shelf holding letter writing ephemera and a UMBC pennant
Part of Caesar’s letter writing station. (Marlayna Demond ’11/UMBC)

One of Caesar’s regular pen pals, Sam, is a student from Belgium, who often sends her two letters a week, densely written on graph paper. His tight cursive isn’t easy to skim, but Caesar has grown accustomed to his handwriting over the past four years. “He’s more prolific than most,” says Caesar, and in addition to his own letters, Sam has also connected her to his mom, Christine. “Her letters were much more colorful and had lively stickers and things in them, while his are utilitarian.” 

After three or four years of letter writing with Christine, Caesar received a note this past December saying she wanted to end the correspondence. “I was sad,” Caesar said, “so I reached out to my letter writing groups and asked, ‘How do you feel when this happens?’”

Pen pal relationships have many of the same ups and downs as in-person friendships, so Caesar shares certain parts of her life more or less with some writers, but all of them know about her love of tea and the Marvel universe. Oftentimes, she’ll receive gifts of specialty tea flavors or themed-stamps, and she attempts to keep her correspondence and gifts focused on the recipients’ interests.

Step 4: Give it your stamp of approval

Getting your letter (or in Caesar’s case, sometimes dozens of letters at a time) out the door is the final step. When Caesar travels, she makes it a point to ask the local post office to add its own unique cancel stamp to her postcards or letters, so the recipients can see where she’s visited.

Once, a pen pal from New Hampshire sent Caesar a letter stamped from Valentine Station in Loveland, Colorado. Caesar was confused until she learned about a service that will send your mail through interesting named locations for a small fee. 

A hand holds a membership card to the Letter Writing Association
Caesar holds up one of her letter writing membership affiliation cards. (Marlayna Demond ’11/UMBC)

Thoughtful touches like these are part-and-parcel being a good pen pal, but they’re not necessary to get started writing letters. “This really does fulfill my creative spirit,” says Caesar, “especially since I don’t get to do this in my daily life—but actually this is my daily life.” 

For aspiring pen pals, Caesar says, start by writing to someone you already know and love. Who knows where your letters will take you after that.

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