Dear Fuck Up: Should I Tell My Friend I've Fallen for Them?

An old question with a twist

I suppose it’s a bit fitting that I should start my first real column with an apology for failing to live up to expectations. I had hoped to have this post up last week, but a combination of factors — some logistical (not a lot of questions yet) and some world-historical (feeling like there are much better and more important things for everyone to be reading right now) — conspired to get me here, shamefully late. There is also the fact that I am not very good at being my own boss. The problem is that I know I’m a petulant employee as well as being a lax manager so when I occupy both those positions at once things become difficult. Forgive me and I promise to try harder to have columns up weekly from here on out. 

Dear Fuck Up, 

This part is pretty straightforward: last year, I realized I was totally stupidly in love with a longtime friend. Happens, I think. Plenty written on that, right?

Here's the complication: I transitioned many years ago, I live as a guy now; I've only been involved with men since. My friend, who I'm stuck on, is not a man. In the course of my life I've been a girl asking girls out, I've been a girl asking boys out, I've been nb asking whoever out, I've been a man asking men out. But I've never been in the position of a man, trying to handle this with a friend in broader woman gender territory. So, I am kinda freaked out about saying anything to her/them.

All my women/woman-leaning friends tell me that they hate when guys do this. That it makes things weird. That it feels like the other shoe dropping, "Ohh, it sucks when a guy finally turns that corner. Once he has feelings, it's so over." And she's a really genuinely good friend, and important part of my life, and if they really would feel like "uh oh, it's THIS thing happening, now what", then I don't want to fuck things up. 

So when I'm trying to think about the actual problems (How does she feel? Is it even worth bringing it up to them at long-distance? Should I ask a mutual friend if the timing is bad?) now I have all these hypothetical people floating around in the room with me all the time, fucking up their friendships and ending up miserable. Is that for real? Are they part of the problem at all, or am I getting psyched out? Or is it like, Classic Clueless Guy About To Totally Eat Shit On This One, to think "but what if we're the rare two adults who can be mature about this"? 

Sincerely,

Haunted House

Dear Haunted,

I don’t think those mature adults are anywhere near as rare as you’re imagining, though I understand why it may seem this way. After all, two people who have weathered a bout of unrequited feelings and remained friends won’t necessarily turn it into a fun story they tell. I’ve had my romantic aspirations kindly shot down by a friend or two over the years, and rejection is never really something you want to broadcast to the world. I have also, on occasion, had to tell a person for whom I had a great deal of affection that it was strictly of the platonic variety, and I wasn’t about to go blabbing to everyone as I’m not a total asshole. 

Nor, by the way, would I think to start complaining about how men just always pull this stuff and isn’t that a big problem for society. Are there some men out there who tend to cultivate female friendships in the hope that it might one day lead to something more? Sure. Do they exist in sufficient numbers to sustain a stereotype robust enough to have survived long past the era of women drinking from mugs labeled Male Tears? I truly do not believe so. It just sometimes happens that you will look at a face you’ve seen countless times and suddenly have the urge to bring it much closer to your own. You will find that a new sense of wonder attaches to a person who is also beautifully familiar. You will realize, in short, that you are in love. There is nothing particularly gendered about this. I refuse to cede the territory of Being Someone Who Yearns to men. 

And it’s worth noting here that the other reason you think it so rare for two adults to be able to handle this situation well is that you’re failing to recognize the guise under which you’ve heard about it before: a love story. For every anecdote about relationships ruined I could give you one about relationships changed. “We were friends for years before we started dating” is so common a story it’s often told quasi-apologetically, like it’s not exciting or interesting enough to count. But in every version of that story there is a moment when someone who had long been living between fear and hope had to pick one. 

I think you are focusing on the risk of being clueless so that you can avoid the real risk of knowing. I just read this great essay on Louise Glück by Sam Huber and was reminded of this passage, from American Originality: 

“Occasionally something will give pleasure, will actually charm or divert or entertain, will, to use that terrifying word, disarm. Insofar as our fearful, compulsive, rigid natures allow, I think we should welcome what follows.”

Nothing disarms us quite like love, which accounts for all the rickety, ad-hoc defenses we construct against it. Defenses like “it’s not worth risking our friendship” or “I don’t want to be a cliche.” But it’s worth it and there are far worse things to be.

It takes a bit of courage to be happy. Surely you of all people already know that. 

Love,

A Fuck Up

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