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How to Survive a San Francisco Break-Up

Updated: Sep 20, 2022 10:51
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This piece is featured in my new limited edition zine Slouching Towards Neverland: 20 Years of Writing About San Francisco.

Find out how to get a hand signed copy right here.

SF break-up

This originally appeared on The Bold Italic on March 14th, 2012. The brilliant artwork for this was done by Heather Tompkins.

I’m currently sleeping on my cousins’ couch in the Castro. Well, that’s not entirely accurate. I’m sleeping on a couch that was mine, and in my apartment until recently, when my girlfriend and I broke up. When I moved out, I took my couch with me, and gave it to my cousins. It’s their couch now and I’m sleeping on it. I kinda feel like a turtle, carrying my home on my back wherever I go.

Strange, right? Well, most things in San Francisco are a little strange, and ending a relationship in this town is no different. From not being able to move out for a few months due to the expensiveness of this city to knowing that the only way you won’t run into your ex is if she moves out of town, breakups in SF might be a special breed. What follows is a little guide to surviving a San Francisco breakup. That is, of course, after you figure out who gets which tutu from the costume box.


When you’ve spent a long time with someone, your lives have a way of melding together; you become an island of two. You have your own language, your own customs, your own way of interfacing with the world that only the two of you fully understand. After a breakup, everything from the Tesora blend at Philz Coffee to the groceries you buy at Rainbow reminds you of the little sovereign nation you used to inhabit. So the best thing you can do is get the fuck out of town for a little while. Go someplace where you don’t have any nostalgic memories with your ex, like Berkeley. Really, when was the last time you actually went to Berkeley? Yeah, it’s still over there across the bay.



With a breakup comes writing sad poetry at Caffe Trieste, drinking too much in Mission District dive bars, and riding Muni to work with a general feeling of malaise. But you know what else comes with breakups? New booty! That means you can hook up with that dude who found you on Facebook and got amazingly more handsome since you last saw him in junior high. You can finally holler at that girl you have a crush on who works at Tartine. You can go home with the redhead who always ends up at the same parties as you. Being single means you can fuck all those people you’ve fantasized about while you were tied up in monogamy. It also means you can finally live out your fantasy of getting tied up. Wicked Grounds did just reopen, you know…

If you’ve been screwing the same person for a long time, it might be kinda weird to get naked with somebody else. But it’s also unbelievably exciting to explore the curves and nerves and tastes and purrs of a brand new body. And sure, they may not do that one thing that your ex used to do. But the first time you hook up with someone is incredibly hot. And more than anything, it gives you an ego boost. It helps you realize that you’re still sexy and attractive and that people want you.


This is San Francisco, a city that’s only seven miles by seven miles. You are, without a doubt, gonna run into your ex. It is unavoidable. If you’re lucky, it’ll be during the daytime while you’re both sober and on your way somewhere else. If you’re unlucky, you’ll be out drunk one night and end up an emotional mess after running into her and her friends at The Residence. If you’re really unlucky, you’ll run into him while you’re drunk and fragile and he’s out with someone else. Most likely, all three of these things are gonna happen. So just be mentally prepared.


Be prepared for the way they have the ability to take your breath away just by entering the room. Be prepared for him to act like he’s totally over it. Be prepared for her to seem happy with somebody else. Be prepared for them to not want to have a drunken conversation with you at Otis about all the things you could’ve done better. Be prepared for them to seem like they’ve gotten their shit together while you’re still an emotional casualty. They likely feel the exact same way as you – they just don’t wanna let you know. It’s called self-protection. It hurts. Be prepared. Shit, you probably can’t. At least try, if not for yourself, then for me. No one wants to see you crying in public, unless it’s because the Niners just lost the playoff game.


This goes along with the last point, but try changing up your routine a bit. If you go to all the same places, you’re more likely to get all nostalgic. Plus, you’re more likely to run into your ex. So, switch from Four Barrel to Blue Bottle. Try the Union Square location of Cafe La Taza instead of the Castro one. Sit on Gay Beach at Dolores Park instead of Hipster Terrace. Hang out in North Beach instead of the Marina.




One of the great things about being single is that you no longer have to take someone else into consideration with every decision that you make. Start saying yes to things you wouldn’t before. Take up that friend on the promised surfing lesson. Go for the midnight bike ride up the wiggle, through the park, and out to the beach. Try dating girls. Have a threesome (that’s what I’m hoping for). Have an “uncool threesome” (you know, the MMF one). Go to the Power Exchange. Do too much blow in Delirium’s bathroom and go home with someone way too young for you. Bang a cougar you meet at Balboa Cafe. Do some shit you might regret but will make a good story eventually. It’s amazing how this all ends up going back to sex isn’t it?


There’re a million reasons not to go there. Just don’t. Plus, do you really think no one is gonna find out? This is San Francisco for fuck’s sake. Gossip moves through this town quicker than herpes.


I know this one can be hard. You’re wasted one night, stumbling out of Beauty Bar, City Tavern, Badlands, or some other meat market and you’re totally underwhelmed by your opportunities. You think to yourself, “I should really call ___.” It sounds like a good idea at the time. The familiarity, the comfort, the fact that you know your itch will get scratched. All I’m saying is that it’s not a good idea. You’re just picking scabs from a wound.


There’s a great line from “Break Up the Family” by Morrissey that goes, “Let me see all my old friends/let me put my arm around them/because I really do love them.” And once you go through a breakup, that shit totally resonates. You wanna surround yourself with people who love you. Plus, let’s face it, you’ve been totally neglecting your friendships. And hey, they might have hottie friends to hook you up with. I especially like to hang out with my married friends and make them jealous with all of my ridiculous dating stories. And they really are ridiculous. How is there not a reality show about the strangeness of dating in San Francisco?


Or any other sad music for that matter. Yeah, I know I just quoted him and all, but sitting around listening to sad-ass music is just gonna make you a sad ass.


Get rid of some of that clutter that piles up during a relationship. Things like your matching Bay to Breakers costumes, the Britney Spears songs that somehow got on your iPod, the stubs from that Giants game you went to last year, that weird piece of furniture you found on the street that your ex insisted you bring home, the shitty piece of art that you’ve loathed ever since she bought it off some kid on Haight Street. But keep the photos – you’ll want those some day. Just make sure you hide them from yourself for a while.


Lately I’ve been thinking that love can only be measured by the scars it leaves. But if that’s the case then maybe a breakup can be measured only by the way you heal. Hopefully, some of the tips above will help you mend. If not, there’s always booze.


Get this limited edition, hand signed zine covering 20 years of Stuart’s writings on San Francisco! Learn more right here.

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Stuart Schuffman, aka Broke-Ass Stuart, is a travel writer, poet, TV host, activist, and general shit-stirrer. His website is one of the most influential arts & culture sites in the San Francisco Bay Area and his freelance writing has been featured in Lonely Planet, Conde Nast Traveler, The Bold Italic, and too many other outlets to remember. His weekly column, Broke-Ass City, appears every other Thursday in the San Francisco Examiner. Stuart’s writing has been translated into four languages. In 2011 Stuart created and hosted the travel show Young, Broke, and Beautiful on IFC and in 2015 he ran for Mayor of San Francisco and got nearly 20k votes.

He's been called "an Underground legend": SF Chronicle, "an SF cult hero":SF Bay Guardian, and "the chief of cheap": Time Out New York.