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The Amazing Thing I Did To Mark My 50th Birthday

It couldn't have been more cathartic.

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An image of a woman licking a letter envelope.
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In high school, Bob held the title of Class Wit. My yearbook was peppered with pictures of him, crazy freckles and the bushy mess of caramel curls he would somehow stuff into a football helmet. At our 20-year reunion, he was still funny and freckled, but completely bald. After we clinked beer bottles, he said, “You changed me in high school.”

This surprised me, as Bob and I barely knew each other. He was a jock, and I fancied myself a twirly hybrid of Stevie Nicks and Emily Dickinson. I doubt he ever would have spoken to me if not for the fact that, as seniors, we both ended up in Mrs. Witte’s public speaking class, an experience that — like being trapped in an elevator — created some unlikely bonding.

Mrs. Witte assigned topics based on the controversies of the day. At the reunion, Bob said my speeches shifted his hard-held opinions about liberals and conservatives. “I didn’t agree with you, but your arguments made sense,” he said. “So, I decided to stop prejudging people and just listen to what they had to say.”

Years later, as my 50th birthday approached, my husband started asking how I wanted to celebrate. I have no appetite for jewelry or travel, and spa weekends seem like something other people do. As I struggled to find something that felt like “me,” my conversation with Bob popped into my head, sparking what seemed like a fun, simple idea.

“To commemorate 50, I’m going to write 50 letters, each one to someone who’s shaped who I am today,” I announced to my husband.

“Really?” he said. “Can’t you just have a party?”

A month before my birthday, I set about making my list. The first batch of names were easy: family members, two ex-therapists, my creative writing teacher at the Adult School. But the rest were names I had to ruminate over, adding someone because I loved them, taking them off because someone else “shaped me” more. It felt like cleaning a closet: pulling everything out; assessing each thing; remembering how it got in there in the first place. Then needing a nap.

My plan was to write all the letters within 30 days. Three months later, I’d written two. And the list was still not finished.

It took years to complete my birthday project — seven, to be exact.

I wrote letters to old friends and lovers, my bestie from grade school, a handful of people I’d worked with, and the hairstylist who convinced me to go long. I wrote to my husband, an old roommate, and the leader of my Weight Watchers group. Many were people I’d kept in touch with; others, I had to track down.

Most letters were typed, a few written by hand. I usually sent them as I wrote them, but sometimes I’d wait. I gave my older son his letter the day I dropped him at college; others, I timed to arrive on the person’s own birthday.

Some people wrote back. Some never responded at all.

A few of my letters were impossible to deliver: to my father, who had died when I was in high school; to the late Dr. Sarno, who cured my 25-year backache; to my third-grade teacher, Ms. Itak, the first to encourage me to write.

I had just finished the letter to my 99-year-old Nana when I received word that she was in hospice care. I flew across the country to deliver it in person. Nana barely acknowledged me as I walked into her apartment; I’m still not altogether sure she even knew who I was. Sitting next to her on the couch, I turned my body to face her, her aide stepping into the hallway to give us the room. Nana stared softly ahead as I read aloud all she’d taught me: how to cut cantaloupes, how to mend buttons, how to be a good friend. I did not end up as tidy as she was, or as generous, but I learned how to hug like I mean it, and how to speak my mind. When I finished the letter, her aide came back in. She led Nana to bed, quietly, while I struggled to find my breath.

At times, I stepped away from my project, often for months. I told myself it was because I was busy, though that wasn’t the whole truth. Writing my letters usually felt good — soul-good. But sometimes it would hurt.

Early on, I thought all 50 would be “love letters,” and many were. However, some were the opposite — letters to people I wished loved me but did not. They shaped me by not loving me, because I’d molded myself to try and be something more to them and, over time, that molding stuck.

My list included boyfriends who left me and a college professor who made me cry. Some of those letters started out angry, and I decided to put them aside before I sent them, sometimes for a long while. After revisiting them, I was often able to see certain relationships in a different light, changing the nature of the letters completely.

The letter to my younger son was one of my most challenging; he is so much like me. Writing it was like looking into a mirror and having to make peace with the most complicated parts of myself.

One of the last letters I wrote was to funny, freckled Bob himself. Just like all the others, I began with the story of how he unwittingly prompted this whole project, though his ended up more of a thank-you note. Because what started with a small, unexpected compliment grew into a huge, unexpected gift: The reminder of how great it can feel to make time to tell someone how they’ve made a difference.

When I tell people about this project, most think coming up with 50 names would be the hard part. But, in the end, my list actually felt too short.

Jessica Wolf is a freelance writer living in New Jersey. Her website is