Devin Dearing Preston: NYC writer, playwright, and storyteller

Tightly Holding On

January 3, 2012

Dear Dan,

I lost that hat you gave me today. And I was upset by how much it upset me. I really loved that hat. I miss it already.

That hat was a premature present. Given to me on our third date, which I consented to primarily because I wanted another nice dinner, if you want to know the truth. The gift was designed to cause me to note your thoughtfulness and generosity. A step forward from past boyfriends, I remember thinking. That possum fur hat, from your weird solo trip to New Zealand, was part of your full court press to win my undevoted love and affection. That’s what you ultimately wanted, love with no attachment or responsibility. I should have given you that fucking thing back when I realized dating me was merely an extended ego trip at best, and down right abusive at worst.

I fell so hard for all of it and you. I was devastated that you made such a large financial investment in me, without being prepared to make an emotional investment of equal value. And I hate myself, because your willingness to float the fiscal side of courtship had more than a little bit to do with why I fell so hard so fast. I think. Even though I never fancied myself the materialistic type. Its hard to not be impressed by gestures that would have bankrupted me, or any of my peers.

The gift of a ridiculously warm hat to protect me from the coldest New York winter in history, might have also been a powerful enough metaphor to allow me to consider a relationship with you a worthy use of my time. Your hat told me you cared.

Also, what former poor girl hasn’t at least entertained the idea of marrying some rich New York City banker. There you were. Showing me that in New York, even shallow, ridiculous dreams can come true. I was in the middle of my own modern fantasy and waiting for the shoe to drop. Which we both know, it did. I saw the warning signs, but started to like you, in spite of the over the top displays of privilege.

You had the means, so you spoiled me blindly and with no restraint. Fancy dinner’s. Romantic nights in fancy hotel’s. Weekends at bed and breakfastes. You even picked up cab fare. I mistakenly felt so special, having never before given much thought to my value. Let alone my actual fiscal worth. At the point I met you, I was just thankful you returned my phone calls and were kinda cute.

I deserve to be treated like this, I remember thinking. He can afford it. Why question his motives. Even if they are carefully wrapped in hundred dollar bills. I stupidly equated the dollar amount spent to be directly reflexive of the amount you cared. It wasn’t. Not even close.

And the spending never impressed me to the point of missing you, Dan, the man behind the Golden american express card. You weren’t some creepy old man trying to buy a sexual escapade with a struggling waitress. I liked you more for your vulnerability and down right shock at my honest interest in you the guy, not you the successful business man. You were so dorky and cute, but in a manly way. I saw your nasty insecurities through the wads of cash, and loved that little guy who felt compelled to buy my affection. I felt compelled to let you.

I told my sister I was dating a banker, and she flatly replied, “Devin. No. ” How right she was about how wrong you were for me.

Once you realized my affections went deeper than your pockets, you took off so fast that the dust left in your wake is the only tangible memory I had of the time I flirted with the idea of loving a troubled rich man. Well, that, and that really warm ass hat.

I told myself it was only practical to keep it. That my holding on to the hope of you coming to your senses and being the man I saw behind the padded bank account, had nothing to do with my continuing to sport that over the top, fur covered, head warmer.
It wasn’t to bring to mind the sweet lost guy who was never fully appreciated for his years at Nerd Camp or for being a bonifaied Eagle Scout. Not appreciated in the way that I was capable of. No. Its because it was warm. Plain and simple. I’m not still holding on to these details of you, a man, who might have been a hallucination, for all I know, for any reason I can justify at this moment. I certainly was not doing so with a winter accessory. I wasn’t. I just loved that fucking hat.

The reality is you didn’t actually want a relationship with me. You just wanted to see if you could get me to want to be in a relationship with you. Congratulations. Don’t feel too proud of yourself. I would date a crack head for three months if he promised to take me to Paris.

I wish that wasn’t sort of true.

Dating you taught me a good deal about my self worth. And that no Wall Street douchebag could put a price on it. Sure, I probably could have stayed on the other side of my feelings and gotten more than just a silly fur hat out of our arrangement. But I’m worth more than meaningless possessions, even if they do cost a small fortune.

And, Dan, you helped me see that. If you weren’t ready to share your self with me, your happiness, your life, than I didn’t care if you bought me a full mink coat. Although, my address is still the same, if you are feeling guilty and want to send me one, you know, to replace the hat, and let me know how truly sorry you are for not being able to put your mouth were your money was. If you want.

Wait. On further consideration, don’t bother. Wearing it would just remind me that it was holding the place of something I valued more than the luxurious fur of woodland carcasses. Love. You didn’t understand it. You wanted it showered on you but couldn’t offer it back in anyway, that didn’t have a big price tag on it. Dating you helped me see that I didn’t want to settle for that. I wanted the priceless displays of affection. The kind of love money couldn’t buy.

So, watching that hat continue toward Brooklyn on the A train, without me, made me take stock of why I had continued to hold on to this symbol of yet another imperfect love in my life, for well over a year now. Just because it was closer to what I wanted, didn’t mean it was close enough to keep around. And, it wasn’t all that cute. So, I said good bye.

Bye-bye hat. So long Dan.

I accepted that my head would be a little colder for the rest of the day. But now that I have finally let that go, out of my life, there is space in my life for a newer, better hat. (If you follow the metaphor) I can even buy one myself these days. And it will bring me more joy than your hat ever did. Because it won’t be lined with regret, heart ache, and empty promises.

Here’s to a new year and more hats than I know what to do with.

Best,
Devin

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Categories: Letters I Will Never Send

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