Why I answer ‘Dear Santa’ letters

Holidays were always a big thing for my family. We’d sneak around, whispering to each other and asking advice for what to get a different family member. Collect intel and share it, maybe go in on gifts together. Find hiding places around the house to stash the gifts purchased until we could sneakily wrap it and place it under the tree. Suffice it to say that my favorite part is figuring out the perfect gift for someone. There might be no bigger high for me than when someone opens a present I bought for them and screams, “this is what I wanted!” I can’t explain why it gives me such joy, but it always has and I’m sure it always will.

Several years ago, I was looking for some way to do volunteer work over a couple weeks off I had from my job. I discovered an organization called New York Cares, with all kinds of volunteer opportunities, but one in particular caught my eye. It was their Winter Wishes program. This was the description:

I couldn’t stop reading the line “many of whom would not otherwise receive gifts during the holidays”. It broke my heart. As a kid plenty of times I didn’t get what I wanted for the holidays, but I was always lucky enough that my parents could afford gifts for me and my brother. I checked my budget and reasoned that I could afford to give two gifts to the program, and I signed up for two letters. Back then you could choose the age group you wanted to be assigned after deciding how many winter wishes you wanted to fulfill.

What followed that year, and every year since has been one of the most amazing experiences of my life. Even my friends each year will ask, “who are your kids this year and what did they ask for?” Which is funny because I do refer to them as “my kids”. I don’t always know their last names or any more than what I read in the letters I receive. Openings like “Hi! My name is Bryce and I love basketball!” Or sometimes just “I would really really like many books to read and maybe a teddy bear too.” I am simultaneously weepy and happy when I shop for these gifts every November (most gifts are due by second week of December). Happy because I do my best to get exactly what “my kids” ask for and weepy because I wish I had the money to answer hundreds of these letters. But over the years, I have convinced other friends and family members to sign up for letters as well, and I know that even getting one more letter answered helps.

This year I signed up for three letters, one from a child, one from a teen and one from a senior (an option that didn’t previously exist). I read their letters and had to google some of the things the teenage girl asked for because I am obviously out of touch on what’s hip and cool these days in high school. I stress about whether I picked out the right eyeshadow palette for the teenage girl, a cool enough looking basketball for the eight year old and a pretty enough picture frame for the senior woman. And I wrap the kids’ gifts every year because I remember that half the fun was always tearing off the wrapping paper and wondering what was waiting inside. I hope that they’re happy and yet still wish I could send more or do more.

I’m delighted to be able to say that over the years I have bought wrestling action figures, stuffed animals, scooters, books, even a Nintendo DS. I have gotten lost in Toys ‘R’ Us, asked really stupid questions about popular toys, ordered two different kinds of doll clothes off Amazon because I couldn’t tell from the picture if I had picked the right one. Called one of the shelters to find out one kid’s favorite color so I could decide on which Barbie outfit would be the best choice. It’s my favorite part of the holiday season.

I know that I’ll never meet “my kids” or be able to ask them, “did you like it?” Or I hope you didn’t already read that book.” Or see their faces when they get to open what I bought for them. But I still consider them my most important relationship of the holiday season.

Oh and FYI! If you’re interested in being a part of it this year, it’s not too late! You can sign up for letters on the site and there’s ways to use Amazon for gift giving if you’re not in the New York area.

[Image via MGM]

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