I Asked 40 People To Write Me A Letter For My 40th Birthday. It Was the Best Gift I Ever Got

It’s good, if perhaps retro, to write someone a love letter. But it’s a little more unconventional to request one—in fact, to request a lot of them. 

For my 40th birthday last year, I swallowed my pride and did just that: emailed just over 40 friends and family members and asked them to send me handwritten letters as a birthday gift. This may seem like a big ask, but to me it wasn’t: have you ever attended a destination bachelorette party or sat through a four-hour baby shower making small talk with someone’s great-aunt? This was a milestone celebration request that could be done in your PJs for the price of a stamp. 

I didn’t set out to ask a specific number of people, I just thought about the people who had played, or still played, a meaningful role in my life. People who knew me well enough that I thought they’d say yes and wouldn’t be horrified at the request. 

Words of affirmation are my love language, so I asked people to reflect on our past, present, or future; on the role I played in their life; and/or to share advice for the years that lay ahead. For the couple weeks before my birthday, envelopes started arriving in the mailbox.  On the morning I turned 40, I read the roughly three dozen that had arrived. 

As I made my way  through this glut of cards and letters and tiny works of art, I laughed and cried for well over an hour. Most people used the guidelines I’d given them, but there were also wonderful surprises: an original poem, a custom Taylor Swift–inspired poster of all my “eras,” a tiny handmade book of “spells” for a happy life, packets of seeds descended from seeds I’d once shared, notes from an conversation about me between my sister-in-law and her daughter and niece. I got a precious glimpse of myself as others see me, like I was eavesdropping on my own eulogy. For someone who has forgone most of the major adult milestones—no wedding, no babies, no house—this simple thing affirmed that the way I lived mattered, that people saw who I was trying to be.

In a time when we often feel disconnected and lonely, I’d wholeheartedly recommend this activity to anyone, for any number of occasions or situations: moving to a new city, weathering a long illness, the birth of a child. It’s easy, inexpensive and customizable, and gives you a gift not only when you receive them, but for years afterward. Everyone should have a shoebox full of love and validation and connection they can dip into anytime.

(Photo: Courtesy of the author)

My inspiration 

This love letter-fest wasn’t an original idea, but one I lifted from Vancouver writer and entertainer Shawn Hitchins, who made a similar request for his 40th birthday in 2020. “It was the height of the pandemic, and I was coming off some life-altering turbulence,” says Hitchins. “Honestly, I was both annoyed and relieved that I couldn’t make a big deal of this milestone. What the moment really called for was something more intimate. If we couldn’t be near each other, if we couldn’t hug or touch or dance, I asked myself, ‘What’s a way of holding each other that feels safe?’ And for me, it was a personal letter.” 

HItchins asked people to take one 8.5 x 11 sheet of paper and “draw, write, colour, collage, or express whatever you want and mail it to me.” The project was not only a birthday celebration, but an opportunity to find creative kindred spirits in his circles. “A blank page can be daunting, and asking someone to fill it with anything they wanted was really a challenge to show up in a new and unexpected way,” he says. “For me, it became a powerful exercise in connection—finding the people who are ready to join me in the next stage of my life.” 

What makes a good love letter? 

In a world where our written communication is mostly electronic fragments, what makes for a standout letter? I asked Lindsay Zier-Vogel, who lives in Toronto and is the creator of the internationally acclaimed Love Lettering Project, which encourages people to write love letters to the places they live and leave them anonymously around the city. She says the key is specificity. “Yes, you love everything about the person you’re writing to, but saying ‘I love everything about you’ does not have as much of an impact as listing three or four very specific things.”

Also helpful is a willingness to be vulnerable. In the letters I received, people were candid in ways they might not be in real life: some people who aren’t prone to talking about their feelings opened up, one person offered an apology for something that happened almost 20 years ago, and one of my sisters actually used the exercise to come out to me. Letters are an opportunity to say the things we might not find the right time (or the courage) to say out loud. 

How to ask for love letters 

The only challenging part of this process? The vulnerability hangover from making the request. This, I assure you, passes, and can be tempered by the way you ask. You can acknowledge that it might seem weird or awkward, but affirm that it’s important to you. And if you really can’t envision making the request yourself, ask someone you love to do it on your behalf.

Here are a few more tips for making your request and some suggested guidelines, even if some people will ignore them (see: my own father, who sent an email that landed just under the wire):  

• Provide optional prompts. Some people might be intimidated by a request that’s too open-ended, and prompts will also help you get the kind of letters that are most meaningful to you. Do you want to reminisce? To get advice or reassurance? Are you looking for something more visual or artistic? Would you love an old photo and the story behind it? 
• Ask for a handwritten note. Getting mail is not only fun, it ensures you’ll have a keepsake. “You can come back to a handwritten note or card in a way that is impossible with emails and texts that just keep piling up,” says Zier-Vogel. “There’s also nothing like reading wonderful things about you written in your loved one’s handwriting. It’s personal and intimate, versus reading something on a screen.” Don’t forget to include your mailing address.
• Give a clear deadline. I sent my email request a month before my birthday, and specified that I’d love for letters to arrive on the big day. This was enough time for people to be thoughtful, but not so much that they could procrastinate. Most people made the deadline.
• Cast the net widely. You don’t need 40 letters, or even 10, but If you’re trying to decide whether to include someone in your request, err on the side of asking. Maybe they won’t do it, but one of my most meaningful letters came from a young colleague I wasn’t sure if I should ask.
  

Above all, remember this isn’t an outrageous request, and many people in your life will be flattered to be asked and actually enjoy completing the assignment. (One friend sent his letter in a notebook, with the suggestion I add my reply and we keep going. Now the notebook travels across the country every few months.) A couple people I hadn’t asked found out about it and sent letters anyway. We all could use a reason to spend some time thinking about the people we’re grateful to have in our lives. By the way, no one refused my request outright—a handful just didn’t do it. That smarted a little, but I tried not to read too much into it, and the disappointment was easily drowned out by the deluge of goodwill.

A gift that lasts

In the end, it will be well worth it. Hitchins ended up scanning all his letters and storing the originals in a safety deposit box. “When I’m feeling homesick or nostalgic, I scroll through the 70 or so pages on my computer,” he says. One standout letter, though, from his Aunt Lois, travels with him wherever he goes.

Inspired by her commitment to love letters, Zier-Vogel’s husband solicited 40 letters for her 40th birthday, and the gift had a profound impact on her. “I had very young kids at the time, and was juggling work and childcare (and losing), and it really felt like there was very little space for me on any given day,“ she says. “Reading 40 letters from people from various parts of my life was the very best kind of overwhelming. They reminded me of how much living I had invested in, and how much love was surrounding me at any given moment.”

My letters are in a shoebox marked “40,” and in tough times, I pull from my own wellspring of reassurance, connection, and delight. Inevitably, these little scraps of paper remind me of the bigger picture. “Life is incredibly short and fragile,” wrote my stepdad. “Enjoy every day.” 

“You’re always planting beautiful seeds in everyone’s minds,” wrote one friend, and I hope this is one of them. Many people mentioned they’re going to steal this idea,and I urge you to do the same—you too may find it’s the gift you didn’t even know you needed.