Love Letter Stories

In my teenage years, I got into the unfortunate habit of writing love letters to girls I had crushes on.

More fortunate: I had the good sense to file away most of these letters and share very few. Unfortunately, I didn’t have the good sense to file away those ones, too.

Not that any catastrophes followed. While I wouldn’t be surprised to learn that recipients chortled over them in private (or even amongst their friends) I was spared any very public humiliation. More than anything, I think the letters just made things a little more awkward than they needed to be. They put feelings that were better left unspoken on display. They provided tactile evidence of what was going on in my head--evidence that might still remain today, tucked in some scrapbook, or perhaps more realistically crumpled up in the corner of a closet floor or beneath a bed, never to be seen again until the recipient’s childhood home is sold and cleaned out. Even then, unlikely to be re-read.

Still, there’s a part of me that stands by the imperfect logic of my youth. I was always better at writing than talking. And while none of my pre-college crushes would really go anywhere, there’s a part of me that’s happy I removed what slivers of doubt I might have had--for every love letter I sent, I can never say, “I wonder if she liked me, too, but she never knew how I felt.”

I know.

Rather than linger on defeats and humiliation, I’d rather focus on two love letter stories that I can look back on and smile, even as I shake my head at my younger self.

In my early teenage years, I spent three summers a couple hours from home at a sleepaway camp. One of those summers, I met Alaina.

Alaina was two years older than me and the single coolest girl I had ever met. She lived in Manhattan during the year, used cool city slang, had cool short hair, wore cool black tank tops, and--albeit in contrast to the whole cool motif I have going here--was incredibly hot.

Alaina and I met when we both signed up for a week-long movie-making activity. We ended up filming a series of skits, and it was in the writing and filming of them that I had my limited interactions with her. After the week was up, I would see Alaina around campus but we never spoke again.

Then I got a hold of her email address.

It’s not exactly accurate to say that I sent Alaina a love letter, though there were many superficial similarities. I wrote her an email after the summer in which I let her know how cool I thought she was. And how I wished I had talked to her more when we were in the same place. I didn’t ask her out or go too far over the top about about my affections or any of that. I was direct, honest, and, for my age, pretty sensible. And I never expected that I’d hear back.

But I did.

Two days after I first wrote her, Alaina replied to my email. She thanked me for complimenting her, and said that of course she remembered me, and that she’d love to get me know me more.

It was the stuff of bad, bad fiction. The cool city girl and the small town nerd striking up a friendship over email. And yet, it happened.

I wrote to her about starting high school and how much bigger the building was than my middle school, and how confusing I found the layout. She wrote to me about readjusting to New York after life at camp, and the movie she had just seen. In a throwaway line, she wrote, “don’t speak too soon, ‘cause the wheel’s still in spin.” In the weeks that followed, I devoured the better part of the Bob Dylan catalog, courtesy of CDs and cassettes available at the public library.

For a month or so, we maintained this pen pal relationship. I had visions of us asking one another for advice, confiding in each other, and maybe even meeting up the next time I visited my grandmother in Queens.

Then she stopped writing.

Alaina didn’t reply to one of my emails for about a week, so I wrote her again. When she didn’t get back to me again, I let it go.

In retrospect, I’m fully aware that I put Alaina on a pedestal, but I’m equally aware that two people with only so much common experience between them are only liable to stay in contact for so long. The school year gets busy. You meet other friends. You move on.

It was as happy an ending as I had any right to expect from that love letter story.

Ready for one more?

I promise the next one is shorter.

I’ll let you enjoy a halftime break with one of pop culture’s great love letters, courtesy of my boy Brian Krakow.

And we’re back.

This second story is all about a dream.

Another year, another girl, and a set of unsent love letters. I finished writing one of them just before I went to sleep one night. In that dream I was on a boat, for a scene something like the 5th grade whale watch my elementary school had sent us on. In this dream, the girl had read my letter, only I hadn’t signed it. I followed her around the boat like a ghost, waiting to hear her reaction.

She loved it.

She loved the letter and said she was in love with whomever had written it.

The funny thing about this dream is that I didn’t rush to tell her that I wrote the letter. Nor did I craft some elaborate, romantic gesture to bring us together. I left her and looked out on the water, studying the way the sunlight reflected off the waves.

I was happy.

And I think that dream sums up what both my love letters and my early teenage crushes were for me, and all that I really hoped to get out of them. It wasn’t about sex, or relationships, or status, or even love, really. It was about expression and affirmation. About little more than today’s hope that you’ll read this post and like the link that I posted on Facebook. Except all of that effort was focused on one person at a time.

I dreamed that a girl loved my letter. And at the time, that was just as good as her loving me.