Courting Disaster: Try a Little Tenderness

Courting Disaster is an advice column on matters of the heart (and loins) coming to you directly from the revolving door boudoir of international queen of hearts, Morgan M Page. A long-time notorious dater from sea to shining sea, Morgan is a trans girl on a mission to solve all problems big and small in your feminist, queer, and trans situationships. Not just any old Carrie Bradshaw, Morgan is the creator of Brazen: The Trans Women’s Safer Sex Guide, and will put her near-decade of experience as a sex educator at your disposal.

Dear Courting Disaster,

My best friend likes me romantically, and we both know and are chill with it. However, I started dating someone and haven’t told them out of fear of hurting their feelings, which I don’t want to do because they are my closest friend. I am four months into this cover up, and I have no idea how to approach telling them at this point. Help? 

Just Friends

 Dear Just Friends,

I’m not going to ask you if you’ve seen classic John Hughes 1986 teen rom-com/class drama Pretty in Pink. I am fairly confident that even the spring-est of chickens have seen this cult movie, which turned thirty last year. So, as I’m absolutely confident that you remember, the plot of this film revolves around Molly Ringwald’s character Andie who is in love with some semi-attractive rich dude (oh, to have such problems) while her quirky lesbian best friend Duckie tries to win her affections and just generally Nice Guy’s it up behind her. Sound familiar?

The best moment in this film happens when Duckie dances his soft butch way into the record shop where Andie works and performs a full drag king number to Otis Redding’s “Try a Little Tenderness” (a classic butch-trying-to-impress-a-femme-pre-2005 move if ever there was one). After this impressive display, Duckie finds out that Andie is actually waiting for a date with the ‘richie’ guy. Perhaps predictably, Duckie doesn’t take this revelation well (“BLANE?! His name is Blane? That’s a major appliance, not a name!”). He spends most of the rest of the film moping about it.

There is a lesson here. Andie didn’t gently break the news to Duckie, she just sort of lets him find out—which is something I think we can all agree was a little thoughtless. It sounds like your secret affair has been going on long enough that it’s only a matter of time before your bestie finds out. And if your bestie is anywhere near the level of riding their bikes down your street 100 times a day, like Duckie, then that is not going to end well for anyone.

Finding a way to gently break the news to your bestie is the only way forward. And this isn’t just to preserve your friendship, when you think about it: if you do care about this person, and I’d wager you do, then you may need to consider the effect not breaking this news may have, not that you should ever take on the responsibility for someone else’s feelings and life choices.

Let me explain in song. In 1962, Donna Reed Show actress Shelley Fabares shot to the top of the hit parade with her single Johnny Angel. This dreamy teen pop number tells a tale as old as time. The young girl longs for this one boy to notice her – her heart fluttering at his every hello. Midway through the song, our love-struck protagonist sings tragically, “(Other fellas) call me up for a date. But I just sit and wait, I’d rather concentrate.

So my question for you would be—is your best friend waiting around for you to someday change your mind and have a Pretty In Pink Alternative Ending (in which Duckie and Andie inexplicably get together)? And if so, how many opportunities are they giving up while they wait for something that, based on what you’ve told me, is not going to happen?

Now, I am the type of hopeless narcissist romantic who enjoys having at least four or five long-term unrequited crushes at a time—how else would I have fodder for my writing, honestly—though I may find this mild agony exquisite, such is not the case for everyone! While your friend may appear “chill” with your current arrangement, your fear that they could take the revelation of your new squeeze (well, new-ish) poorly leads a girl to think you know they are not quite as chill as they say.

All the more reason to come clean and set this bird free. But how do you do that?

Normal people might tell you that sitting down with your bestie and gently—tenderly—explaining that you’re starting to get serious with your new suitor. Or even taking the slow approach of offhandedly mentioning them here and there in conversation until your bestie gradually acclimates to the idea of this person like a fish being lowered into a new bowl inside a bag of water, would be the best way forward. But, as I once shouted at my beleaguered parents, I am not normal people!

Instead, I suggest you get creative. Write a message in a bottle and just assume they’ll find it at sea someday. Hire a sky writer. Send them one hundred roses that each carry a single word which, when assembled together in the right order, explain that you are seeing someone now but still value them as a friend. Or, to follow the theme of subterfuge and dancing on the edge of rom-com, invite your bestie and your beau to an event together and pretend to meet your beau ‘for the first time.’ All of these are strategies I would file under bad ideas that are just tempting enough to try.

Whichever strategy you decide on, if Pretty in Pink is to be believed—and since I consider Hollywood my Bible, I’d tend to believe it—then your bestie-like-Duckie may end up having an original theatrical ending about it in which they realize that your friendship is more important than their unrequited feelings (and that the Nice Guy/friendzone is a made up misogynist fantasy). And all will be well as you walk off into the foggy parking lot of life with your new(-ish) gender-ambiguous beau. Your now-free bestie might even find their very own Kristy Swanson in the process.

Send your feminist, queer, and/or trans dating problems to Courting Disaster at