Why I’m Not Giving up on Writing Love Letters

To write and be written to in return is a wonderful thing.

Jessica Rosales
P.S. I Love You
4 min readOct 13, 2018

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A few days ago, I went to my desk with my laptop and a cup of coffee. Faced with the dilemma of not being motivated and inspired enough to work, I ended up procrastinating (i.e. cleaning my room).

It wasn’t long before every drawer was purged, knickknacks were categorized and organized into piles, and the floor was carpeted in a sea of papers. In the midst of this pseudo mental decluttering — because a tidy workspace means more productivity, right? — I came across a black tin shoebox that I had repurposed into a container for my memorabilia.

As if the mess at hand wasn’t enough, I opened the tin box and began browsing through its contents. Inside were brochures from travels, notes from classmates, and a couple of birthday cards.

I continued to dig through the files until I unearthed a crinkled envelope that I immediately recognized: it was a letter from my high school sweetheart, now my ex-boyfriend.

My high school sweetheart and I wrote plenty of letters over the course of our relationship, but I didn’t realize just how many letters we’d exchanged until I went through that box.

There were sheets of paper torn out from notebooks, creased and softened along the sides that were folded and unfolded, again and again — notes we had exchanged during class.

There were Post-It-sized sheets filled with his boyish handwriting, so condensed that the square of paper might have more closely resembled the texture of gravel or television static — these were from college.

There was even a letter written on the back of a photograph of our teacher at the time — an inside joke between us. Who knew something as dumb and mundane as that would still make me laugh all these years later? A huge wave of nostalgia swept over me.

And it got me thinking about love letters.

This boy who had written to me so eloquently and prolifically had set the bar a bit too high and may (or may not) have skewed my expectations on relationships.

Call me stupid, but it was only when I began dating other people that I realized that:

(1) writing letters was not a mandatory gesture between lovers, and

(2) it wasn’t common.

Which is understandable considering that not everyone is comfortable with writing; some people communicate much more effectively in other ways.

But it seemed to me that love letters became more of a rarity as time went by.

“Wow, people still do this?” My ex-boyfriends

Receiving a love letter post-adolescence seemed juvenile, almost novel to some of my past boyfriends. Whenever I (awkwardly) handed over a letter, I could tell by the confused look on their faces that they were slightly taken aback. I could practically hear them saying, “wow, people still do this?” Nevertheless, they were always received warmly, so I continued to write.

But here’s the thing about love letters: it’s not a one-sided gesture. It’s an exchange.

As much as wanted to continue expressing affection via pen and paper, at some point, I just stopped—not because my feelings dwindled, not because the relationship was in turmoil.

I stopped because I didn’t receive a letter in return. That may sound selfish, but hear me out.

As with any other means of expressing affection, there needs to be some sort of reciprocation.

When someone you love reaches for your hand, you hold it. When they wrap you in an embrace, you put your arms around them. When someone kisses you, you kiss them back.

If they don’t hold your hand, hug you, or kiss you back, what kind of relationship would that even be?!

Jokes aside, circumstances may change, relationships may end, and the letters you’ve received from a certain person may end up in the garbage — or in a black tin shoebox hidden under the bed if you’re a hoarder like me.

We don’t have any way of knowing whether a relationship will last, and by no means does exchanging letters guarantee a successful, loving relationship.

Case in point, I’ve broken up with my high school sweetheart.

But even if we’re no longer together, those love letters encapsulated some happy (albeit melodramatic) snippets of our time together, and I remember them fondly.

To write and be written to in return is a wonderful thing. And should the person you’re exchanging letters with turn out to be the love of your life, how nice would it be to look have all those letters to look back on?

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