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The handwritten letter by President John F. Kennedy to a purported paramour seeking to set up a liaison is one of several Kennedy-related items being sold at auction.
Associated Press
The handwritten letter by President John F. Kennedy to a purported paramour seeking to set up a liaison is one of several Kennedy-related items being sold at auction.
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In high school, I met this guy. When my then-boyfriend broke up with me, I grew very fond of my new friend. He confessed his feelings for me after I decided to go back to my ex. He began to date a girl three months later and completely stopped talking to me. My heart dropped when he ended up in my first class in college. We talked once, but he ignored me completely after that. He greeted me one time before he left to join the military. He just married the same girl last year. I’m truly happy for him. My biggest regret after five years is not telling him how I felt. I wish I could write him a letter telling him how much I truly cared about him, but I am scared of anything that could go wrong. Should I write to him or should I just try to forget the one that got away? —Hopeless Romantic

Dear HR,

You know, I’m torn over your letter. A large part of me thinks it’s a REALLY unwise idea for you to write to a married man and confess your love for him. A smaller, quieter part thinks you should send it. Not because I think he will leave his wife and run away with you—he probably won’t—but because it might be cathartic for you, help get this guy out of your system and realize he’s not the one for you. Let’s look at some scenarios.

You pour your heart into a letter and send it to him. He either …

style=”font-weight: 400;”>Doesn’t respond at all

style=”font-weight: 400;”>Responds angrily and tells you off

style=”font-weight: 400;”>His wife responds angrily and tells you off

style=”font-weight: 400;”>Tells you he feels the same but it’s too late to change anything

style=”font-weight: 400;”>Tells you he feels the same and plots to dismantle his life so he can be with you

Are you prepared to deal with any of those outcomes?

You say you’re truly happy for him, but that means respecting his life choices and his relationship. It sucks that he blew you off and didn’t want to remain friends, but I can’t fault him for doing so. It’s how we move on, after all.

What I would do is this: Write that letter, pour your damn guts out, project your wildest fantasies onto the page, and deepest regrets. And then tear it into pieces and light it on fire. The letter will represent you, a former you. A you that no longer exists. A you that is trapped in the past, HR, stuck on a hope that has long since sailed.

It’s time to look for another shore. Honor your feelings for him, but do not let them stifle you as they are now. It may help if you reframe the situation. He’s not “the one who got away.” He’s a guy you chose not to be with in high school. He’s not an ex. And, frankly, not even the greatest friend, considering how little it took for him to never speak to you again.

It’s easy to project and wonder if someone might have been “perfect” for us because typically those people haven’t been around long enough to disappoint us. Rest assured, he would have. And you would have disappointed him in return. That’s part of being human.

You are young and have a vibrant life ahead of you. Let this experience shape you for the better and make you more resilient. As Jordan Belfort, aka the Wolf of Wall Street, once put it: “No matter what happened to you in your past, you are not your past; you are the resources and capabilities you glean from it. And that is the basis for all change.”

Anna will be reading some lesbian sex haikus and doing some live advice-ing at Women and Children First on June 16 and invites you all to come!

Anna Pulley is a RedEye contributor. Got a question of your own? Email redeyedating@gmail.com. Or let her send you overly personal emails here.