By Sophia Yakumithis

Well, this will be embarrassing to read after we break up, but here goes nothing.

I’m dating a sad boi. I kind of hate that that’s the stereotype he fits, but he says it himself, so who am I to judge. 

If you are a Boomer and reading this, allow me to explain. A sad boi is a teenage to young adult male who overthinks everything and listens to vaporwave music to cope. He usually has a piercing or two, wears Vans and makes playlists while wallowing in self doubt. And yeah, I dig it.

To give you some background, Boy, as I will be referring to him, and I met through a grassroots exchange where we actually knew each other in real life. Shocking, I know. That means we got all the dirty work out of the way early on and learned about each other’s baggage before anything got serious. Not that I have much.

Unfortunately, a 640 mile distance barrier is preventing Boy and me from celebrating Valentine’s Day together in person. But it’s not like we would celebrate even if we were in the same city. 

We self-identify as too edgy to celebrate any holiday that acknowledges the fact that we love each other. When Boy and I went to Paris — deemed as “the city of love” — I don’t think we even kissed or held hands. That’s a sad boi power move, if you ask me.

However, if we did celebrate together, I would have to make arrangements tailored for a sad boi. And since I’m sure a lot of people out there are also dating a sad boi (or trying to swoon one), I thought planning the perfect day might be useful. 

Venmo him for an oddly specific purchase

That vinyl you know he wants but can’t afford because he spends all his money on cold brew and obscurely flavored SunChips? Venmo him exactly $21.98 and title it “Fresh Air – Homeshake,” or the album of your choosing. He’ll not only understand this cryptic message immediately, but he’ll probably cry that his S.O. is vibing with his current music feels. 

Take him to an edgy coffee shop

…so he can stare into your eyes and overwhelm himself with the fact that he’s dating someone so much cuter than he ever imagined. This might make you uncomfortable, but cortado in one hand, croissant in the other, he will be in sad boi heaven. 

Boy and I call this “staring boi hours.” Just hold onto the dirty mason jar a barista named Clove served your iceless iced coffee in and appreciate the fact you’re with a new wave emo who loves you so much.

Make a playlist

Rex Orange County. Beirut. Pinegrove. If you can make a playlist with artists who have him feeling a certain way, you’re getting lucky on Valentine’s Day — assuming that’s your goal. But he might cry during sex. That only means it worked. 

Go for a long night drive

This is the quintessential nightcap as it gives him the opportunity to deeply reflect on your perfect, sad boi day together. You also have an entire playlist to listen to while you drive in silence. You should drive, though, so he can lovingly hold your hand in his, play with your rings like they’re fidget spinners and pensively stare out the window, pretending he’s in a music video. 

With these ideas on the table, you’re bound to have the saddest, sweetest Valentine’s Day ever. Have fun, my sad friends. And Boy, if you’re reading this, I can’t wait to stare at your face IRL in the near future.