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Letters to Dean Winchester

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Sep 4th, 2004

Dear Dean, 


There have been many times over the past few years where I’ve been so close to talking to you or writing you a letter, but I didn’t know how to approach it or you. Every time I saw you, you went out of your way to avoid me (which I suppose I understand), so it was difficult to know when the right time was. Or if there ever was going to be one.

I’ve come to realize that there never will be unless I step up and do it. I told you a lot of things that day on the stage in high school or that day right before graduation, but I don’t think I said the things I wanted to. When I moved away for a little bit and experienced life, I had a whole different understanding of everything. In fact, my time in Round Rock was one of the hardest points of my life. I was away from family, in a place where I only knew Charlie, and new to the whole adult life I was trying to lead.

Never mind trying to love anybody or explore my own sexuality. But I tried. It was then that I discovered I was grey-romantic and asexual. In fact, I’m sure that what I felt for you may not have even been love. What I loved, honestly, was our friendship. I think we understood each other very well without even trying; it was just an instant connection, in my opinion.

Unfortunately, all of that changed when I started pursuing a relationship with you, and I’ll admit that it was me. But not for the right reasons. I didn’t want to lose you as my best friend and I think that’s all it really came down to.

You were there for me when my dad got sick and you were there for me after he passed, but I was really, really messed up after witnessing what I did. I was clinging to the past and afraid to move forward. As a result, I clung to you and I did things to hurt you, me, Aaron, and eventually Lisa, but I wasn’t alone in that. None of us were mature enough to really gage how much of an impact we had on each other.

High school was extremely difficult. I felt isolated because a lot of our “friends” were ignoring me or spreading rumors because of what happened between us, but now I can see that that was the best thing to happen to me at that time. I discovered who really cared about me. Because of that, I left high school with a handful of friends that I consider my family today.

And I’ll be even more honest, all the stuff that happened between us, both good and bad, was probably one of the greatest things to happen to me. It got me to completely disregard love and sex and because of that I was able to focus on what really mattered to me. My passion for writing hasn’t faltered since then.

Everything that happened between you and I feels like a lifetime ago, but it all still weighs heavily on my heart because I feel like there was a lot of things left unsaid and that bothers me the most. One day, we just stopped talking. At the time, I didn’t understand it, but now I do. Now, I don’t hold any bitterness in my heart at all. I haven’t in a long time, but I feel as though you do because you don’t even look at me. It’s like you’re afraid of something. And I don’t say that as an insult, just as something I’ve noticed.

I remember telling you that I hoped we could be friends again one day and you agreed (you might’ve just agreed to get me off your back but I don’t think so because I never knew you to run away from stuff like that), so, right now, the thing I hope for the most is closure. I hope we can be on friendlier terms instead of just holding something weird and possibly negative between us.

Everyone in life should be able to walk around without feeling weird towards anyone. Everyone deserves their own happiness. Everyone deserves to be able to talk about how they feel.

I also heard about you and Lisa and I just want you to know that I’m not writing you because of it. If anything, I genuinely hope that you two either find happiness with each other once again or you both create your own happiness with other people. Really, everyone deserves that. I can’t say that enough.

I am writing to you because I wanted to say thank you. For our friendship and what it led me to. For whatever else we shared together as well, the infatuation and the pain afterwards.

You can ignore this letter, I would understand, but I do feel that since I’ve said my piece, it’s only right that you have a chance to say yours as well.

I hope this letter finds you, Dean, and finds you well.