In 2019, Samantha Dunn was in prison in Alabama and expected to be homeless after she was released. 

Dunn said she had been exchanging letters with a pen-pal on the outside for a while before this point. Near the end of her sentence, Dunn received a letter from her pen-pal asking what she would do after being released. Dunn said she wrote back, telling her that she “was going to be homeless.”

“She actually offered: ‘Do you want to come to Chicago?’” Dunn said. “With the amount of work that she did and the amount of work I did, I was able to relocate and come to Chicago, and we stayed friends. We’re still friends to this day.”

Earlier on in her sentence, Dunn felt isolated from the world as she started to “lose a lot of ties to family and friends,” she said.

“When individuals get convicted and they go into prison, early on, they may be getting letters from family, from their friends,” Dunn said. “But life goes on out here, people start getting busy, and the letters start getting less. The people on the inside, and I could speak for myself, I started feeling like I was being forgotten.”

Dunn said she then reached out to Black and Pink, an organization that connects LGBTQ+ incarcerated people with pen-pals outside the prison system. Dunn said she began the organization’s matching process, in which Dunn sent out an introductory letter and was chosen by a pen-pal.

“It took me a little bit before I received my first letter, and it was heartwarming because I knew somebody chose me,” Dunn said. “They read my letter and something about what I wrote caught their attention.”

Dunn said she began exchanging letters with her pen-pal periodically, updating each other about what was happening in each other’s lives.

After relocating to Chicago with her pen-pal’s help, Dunn, 50, now works at a Chicago composting company and volunteers at Black and Pink – now called Pushing Envelopes – helping match other incarcerated people with pen-pals.

“It was those letters that made me feel wanted, made me feel loved, that helped me increase my motivation to be a better person, to know that I’m not a failure or I’m all alone,” Dunn said.

Dunn is part of a community of people who still write letters, one that’s fading away: according to a 2021 poll by CBS, a majority of Americans have not written a letter in the past five years. Additionally, 15% of Americans have never written a personal letter in their lives.

Anna Walker, a salesperson at the stationary store Paper Source in Evanston, said that the focus of the store used to be on custom letters and cards, but now the store mostly sells ready-made cards that don’t have space for personal writing.

“[Writing custom letters] had a bigger, trendier moment in the 90s and early 2000s,” Walker said. “As more email invitations or Facebook invitations got more popular, there just weren’t as many people doing that and probably less money willing to invest time and money into it.”

Even though letter-writing is becoming less and less popular, many still use it to find solace, like Margaret Fiorio. Every February, Fiorio, a Chicago-based mental health counselor, writes over 100 valentines for her friends and family.

“I don’t know if you’ve suffered through a winter in Chicago,” Fiorio said, “It’s dark, it’s depressing, it’s a really hard time.”

 “People are like, ‘January has been a really hard month for me, and you sent me a valentine,” Fiorio said. “Thank you so much!’”

For Fiorio, 37, the practice of letter writing began during freshman year, which she said was “a really rough year for me.”

“I started writing letters and friends wrote back,” Fiorio said.  “It definitely is a form of self-care for me.”

She now writes letters around three times a week to her friends. 

“One of my closest friends is a pen pal,” Fiorio said. “We worked in New York City and we sat and we both realized we like writing letters. We’ve remained friends just writing letters back and forth for over a decade now, which is pretty unique and pretty special.”

Fiorio said she loves how a handwritten letter is “so personal, especially during these times where communication is fast.”

“When you’re writing a letter, you’re engaging in a kind of correspondence, you are reflective. You’re talking about your life,” Fiorio said. “And so it’s slowing down. 
It’s being intentional, and it’s really something for me. I’m doing this because I love sending mail, but I have no expectations to get anything back.”

Samantha Dunn said that some prisons have begun allowing inmates to email, but letters are still favored when writing to incarcerated people, since prisons charge the inmate heavily for writing an email at a computer.

“I have a pen pal who is at the Pontiac prison, and we write letters but we also will send an email,” Dunn said. “But, we actually enjoy receiving a letter, because you can’t draw a smiley face on an email. You can’t draw little designs on an email, but you can on a letter. And that’s where it becomes more personal.”