I recently experienced my first date. The date went well, and we had fun, but it seemed to fall apart after that. The timing wasn’t good. I still haven’t quite gotten over her, so I wrote this unsent letter to express my feelings to myself. I did not know that a human being could feel such positive emotions as the two weeks I had with her, or the ongoing pain of rejection that I experience in the weeks after. I’ve never done anything like this before, and I hope that I can move on someday. The names and dates have been changed to protect the innocent.

Lauren,

All of my closest friends (men and women alike) have told me that sending this email is a terrible idea. I think they’re all absolutely right. But there is a little gremlin in my mind that says you are worth it, and I haven’t found a clever way of caging it. Have you ever seen Inside Out? I think I have a deeper appreciation for that movie now.

When I sent you that IM on October 23rd asking about your going away luncheon, I was genuinely concerned that you did not have one, but that wasn’t the whole story. For a variety of reasons, I was interested in pursuing a relationship with you. I would never date a coworker, and my surprise at learning you were leaving compelled my hands to open that IM window and talk to you.

Over the next two weeks, I had conversations with one of the warmest persons I’ve ever known. As I learned more about you, I discovered that we had so many things in common, and I couldn’t help but fall for you. You are a truly beautiful person. You have strength of character, intelligence, and drive, but you are also emotionally vulnerable and caring. You display a maturity well beyond your years that made me think you were older than you were, and I became insecure about my age when I learned yours. I can’t understand how anyone would ever purposefully give you up.

While I don’t know exactly what’s been going on in your life, I respect your boundaries enough not to ask about extremely sensitive topics. However, I do want to know, and for better or worse, I do genuinely care about you. If you meant what you said in your email to me after the race, then I think you want to know more about me as well.

If you haven’t figured it out yet, I’m a fairly impetuous person. I speak from the heart and sometimes let my passions speak for me. This is a characteristic of everyone in my family, but it also makes me someone who doesn’t bottle up emotions or have a hard time discussing my feelings with others. For the past several months, I feel like I’ve been flailing around, making mistakes and stepping on landmines that could have been avoided in hindsight. One thing I learned out of this experience is that relationships are really a team effort. I need you to help me look good. I need you to draw me a map and help me find my way across the DMZ.

At the same time, I want you to find yourself and to be a unique individual with your own identity. I struggled with that all my life, and I finally know who I am and what I want, and I have no problems saying that to you. I know that you went through some difficult times, and I would never impose myself on you or your dreams. You deserve to be happy, and I want to be on your team. I’m not a religious person, and I don’t believe in soulmates or fate. What I can say, though, is that I want to try navigating this celestial existence with you as my co-pilot. I’m willing to absorb the pain if it doesn’t work out. That’s my choice.

Respectfully,

Jacob

Update: I sent this to my dad. This was our conversation. It made me feel better. :-)

Dad: Did you send that?

Me: No. That’s why it’s called ‘unsent’. I wrote it for me.

Dad: Interesting. Did you respond?

Me: lol