To Sir, with Love

I look down at my thumbnails, at the chipped pink polish I probably should have removed three days ago.

“I know what I don’t want,” I say, still not looking up.

“That’s a start. Let’s hear it.”

“I don’t want to break my promise to Dad. I don’t want to disappoint Lily and Caleb.”

“And that’s enough for you?”

He asks it gently, curiously, but I can’t bring myself to answer, not out loud. I don’t want to answer.

But somewhere deep inside me, the answer whispers anyway. No. That’s not good enough. I want to be brave enough to go after what my heart wants.

I want to be bold. Daring.

Happy.

I take a deep breath, both exhilarated and terrified when I realize what I have to do.

To Sir, out on a shaky limb,

I apologize for the radio silence. I’ve been sorting through some of the messier bits of being human as of late. Do you ever ask yourself the big questions and realize you don’t have a clear answer? What sort of person do I want to be? What sort of life do I want to have? With whom do I want to live that life?

I know I’m a kind person, or at least I try to be, but I’m also realizing I’m bit of a chicken in a lot of ways. More obsessed with the dream than doing the work to make the dream a reality.

I live a good life—I do. But I’m learning it’s a life lived largely for the people around me, to support their expectations, to never rock the boat, to never let anyone down. I feel trapped, but how does one find that balance—to be true to oneself without being selfish?

The one area I’ve always thought I was in control of, the one area lived for me, by my standards, is my personal, romantic life. And I know I’m overstepping our usual topics of conversation, but I feel I’ve misstepped here as well. I’m alone, and on some level, I’ve always known that’s of my own making, but now I can’t help but wonder if there are opportunities missed, chances lost, connections I never let happen.

I’m rambling now. This is the longest message I’ve ever sent, by far, and I apologize if I’m destroying what we have, moving us from pithy quips to something altogether a bit more maudlin. Especially since I haven’t shared this with anyone in my “real” life, which I guess leads me to this:

Life feels most real when I’m writing to you, when I see your screen name in my in-box. I don’t know your name. Your face. Your age. But I have the sense I know you. And that you know me too, in a way perhaps nobody else does.

So if nothing else, even if I’ve scared you away, I want you to know that when I’m old and withered, saggy and gray, I will look back on these days, and you, my friend, will be a bright spot.

Lady

* * *

My dear Lady,

I’m not quite sure where to begin. I suppose, most obviously, you haven’t scared me away. You haven’t ruined things. I’m here. And perhaps now it’s me who’s making things weird, but I have a hard time imagining a version of my life where I won’t be here for you, however you need me.

You’re real to me too. You’re important to me.

I’m honored to be your confidant. Everything you’re saying is valuable, and I mean this when I say: relatable.

I mentioned recently that I ended a relationship. The truth is that relationship had run its course long ago, but I’d stayed in it for the sake of someone else. In that way, I suppose leaving the relationship was selfish, and I know I left disappointment in the wake of that breakup. But I also know that we get only so many trips around the sun. Having “met” you, I know that on as many of those days as possible, I want to feel the way I feel when I see your screen name in my in-box.

Yours in have I ruined this?

Sir

* * *

To Sir, with an aching throat,

You’ve ruined nothing. Indeed, you’ve only made whatever we have a bit more lovely. And it’s here that I take the biggest risk of all:

Would you like to meet?

Lady

Sixteen

He doesn’t write back. Not that day. Not the next.

Three days later, I still haven’t heard from Sir.

I try to tell myself it doesn’t matter. It shouldn’t matter. I tell myself over and over that a person I don’t even know shouldn’t have that much power over my happiness.

But I meant what I said in my last message. I do know him. It’s silly, it’s romantic, it’s maybe straight-up nuts, but I know in the depths of my heart that I’ve shared parts of myself with him that I’ve never shared with anyone. And I thought it had been the same for him.