• Click through the gallery for a roundup of all the ways SF makes breakups harder.
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Click through the gallery for a roundup of all the ways SF makes breakups harder.
Click through the gallery for a roundup of all the ways SF makes breakups harder.
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At the end of the day, it's a small city, so get ready to see your exes everywhere... San Francisco is a city of about 865,000, and never does that number feel smaller than when you're trying to avoid one person and can't stop running into them at every bookstore, bar and dim sum spot you've ever loved. What's a broken-up couple to do when they share the same haunts and there aren't enough good dives to go around? My strategy thus far has been to literally hide, but I am open to your suggestions, dear reader.

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At the end of the day, it's a small city, so get ready to see your exes everywhere... San Francisco is a city of about 865,000, and never does that number feel smaller than when you're trying to avoid one

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Photo: Thomas Winz/Getty Images/Lonely Planet Images
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...Especially along SF's few high-functioning transit corridors. At times, BART and SF's most popular bus lines can take on all the worst qualities of a college reunion (people you used to be intimately involved with and all of their friends, occasional screams, someone peeing in the corner) with none of the qualities that make college reunions bearable (beer). This is the real reason why we need a second transbay tube.

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...Especially along SF's few high-functioning transit corridors. At times, BART and SF's most popular bus lines can take on all the worst qualities of a college reunion (people you used to be intimately

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Photo: Paul Chinn, The Chronicle
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There aren't enough desolate but not-gross streets on which to cry.  A couple weeks ago I tried to take a tearful little walk in the vicinity of my office building while blasting some early-2000s sad jams on my headphones. I just wanted to mope and then maybe write something sad about my moping, like a less-racist Morrissey. But I was shaken from my reverie by the sight of a dude full-on Winnie the Pooh-ing* and dropping a deuce in the street. Chastened, I returned to my office. 

*Shirt on top, nothing on the bottom
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There aren't enough desolate but not-gross streets on which to cry.  A couple weeks ago I tried to take a tearful little walk in the vicinity of my office building while blasting some early-2000s sad jams on ... more
Photo: Paul Chinn / The Chronicle
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SF's steep prices mean your post-breakup glow up is going to cost you…
It happens to us all. Your breakup shakes you from your state of semi-hibernation and you look down at your doughy middle, your unshaven legs. "Uh oh," you think. What follows is a ritual as old as time: cultivating the revenge-bod. Even if your parting was amicable, there’s something soothing about single-mindedly devoting yourself to the task of trying to become as attractive as possible in the aftermath of a separation. But because San Francisco is so expensive, get ready for paying for pampering to bleed you dry. Joining a gym? Expensive! Massages? Expensive! Haircuts? Expensive! Also, prepare to learn that you possess physical flaws you did not even know were things (hello there, under-chin fat).
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SF's steep prices mean your post-breakup glow up is going to cost you…
It happens to us all. Your breakup shakes you from your state of semi-hibernation and you look down at your doughy middle, your unshaven
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Photo: Dash - Fotolia
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…And people are so healthy here that the bar is too damn high. 
In a city like New York, replete with sleep-deprived neurotics (my people!), all you have to do is stop smoking cigarettes for a week and go to SweetGreen a couple times to feel like you’re ahead of the curve, health-wise. In wellness-obsessed San Francisco, where tech bros are literally getting the blood of teens transfused into their bodies to beat back the creeping advance of death, that’s not going to cut it. Soon you will go from eating noodles in bed to contemplating questions like: Do I have to do keto now? What is spirulina and why is it in my smoothie? (Learning what spirulina is will only make that latter question even more distressing). Why is everybody fasting? Please send help.
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…And people are so healthy here that the bar is too damn high. 
In a city like New York, replete with sleep-deprived neurotics (my people!), all you have to do is stop smoking cigarettes for a week and go to
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Photo: Getty
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Moving is a special hell here. Between the impossibility of finding a reasonably priced apartment and movers so swamped with people trying to leave that there's a U-Haul shortage, leaving the digs you share with a partner is especially brutal in SF. And if you try to lug your stuff from one place to the next by yourself, have fun with all the hills and impossible parking.

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Moving is a special hell here. Between the impossibility of finding a reasonably priced apartment and movers so swamped with people trying to leave that there's a U-Haul shortage, leaving the digs you share

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Photo: NoDerog/Getty Images
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Uh oh, now you have to date tech bros. There is something uniquely dispiriting about taking a walk post-breakup and coming to grips with how much of the dating pool is clad in basketball shorts and zipping past you on Bird scooters with nary a care in the world, off to spend some of their six-figure salary buying some bulletproof coffee or Dragonchain or heaven help us, a Onewheel.

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Uh oh, now you have to date tech bros. There is something uniquely dispiriting about taking a walk post-breakup and coming to grips with how much of the dating pool is clad in basketball shorts and zipping past

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Photo: Jordan Siemens/Getty Images
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And the apps make everyone too picky. It's an inevitable side-effect of swiping culture that everyone thinks they can do better. Getting the self-esteem boost you crave after a breakup can be challenging when even the scooter people are scooting along to see what else is out there.

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And the apps make everyone too picky. It's an inevitable side-effect of swiping culture that everyone thinks they can do better. Getting the self-esteem boost you crave after a breakup can be challenging when

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Every article about Bay Area dating culture makes you want to go live in a cave forever. People who describe polyamory as a data-driven disruption to monogamy? Pass. Cuddle puddles full of venture capitalists? It's a no from me, dog. less
Every article about Bay Area dating culture makes you want to go live in a cave forever. People who describe polyamory as a data-driven disruption to monogamy? Pass. Cuddle puddles full of venture ... more
Photo: RICHARD PERRY, New York Times
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Maintaining a strong support system of friends is hard in a city full of transplants. At SFGATE, we're constantly writing about people fleeing the Bay Area for regions where housing costs are less insane. The turnover of people is a well-documented fact of life here. But with people constantly leaving, it can be hard to cultivate the years-long friendships that help provide support in the wake of a split. less
Maintaining a strong support system of friends is hard in a city full of transplants. At SFGATE, we're constantly writing about people fleeing the Bay Area for regions where housing costs are less insane. The ... more
Photo: Getty
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No splitting expenses probably means big lifestyle changes. Lately I've been thinking a lot about a post on a Bay Area blog, the Bold Italic, asking creative freelancers how they make their finances work in SF. They had a variety of strategies, but what stuck out to me immediately was that all but one had something in common: They all lived with their partners and split expenses. Going from being part of a two-income household to flying solo in SF can easily take a person's budget from tight to untenable. less
No splitting expenses probably means big lifestyle changes. Lately I've been thinking a lot about a post on a Bay Area blog, the Bold Italic, asking creative freelancers how they make their finances work in SF. ... more
Photo: Shutterstock
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Want to talk to a professional? Lucky you! There's a therapist shortage. Studies say there's a shortage of mental health professionals in California, and it's predicted to get worse (although it's worse in rural areas than around the bay). So if you've decided now is the time to take on your fear of abandonment, you'd best get in line. less
Want to talk to a professional? Lucky you! There's a therapist shortage. Studies say there's a shortage of mental health professionals in California, and it's predicted to get worse (although it's worse in ... more
Photo: Getty
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You feel guilty because in the grand scheme of things, your problems are so small. Everyone likes to indulge in a bit of self-pity after a breakup. But it’s hard to feel sorry for yourself for long when you’re surrounded by so much entrenched human misery on SF's streets. It's hard to wallow when you’re constantly reminded how much worse so many others have it. A walk around the average San Francisco neighborhood can make processing the small, ordinary hurts in one's life feel self-indulgent. less
You feel guilty because in the grand scheme of things, your problems are so small. Everyone likes to indulge in a bit of self-pity after a breakup. But it’s hard to feel sorry for yourself for long when ... more
Photo: Gabrielle Lurie, The Chronicle
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Everybody else is getting married, apparently. Long a bastion of people who married late or not at all, San Francisco recently experienced a huge surge in the frequency of nuptials. The marriage rate has increased a staggering 52 percent since the 2007-2008 fiscal year, the assessor-recorder's office said in February. And with it, a 52 percent increase in our fears of dying alone.

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Everybody else is getting married, apparently. Long a bastion of people who married late or not at all, San Francisco recently experienced a huge surge in the frequency of nuptials. The marriage rate has

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Photo: Alyson Aliano/Getty Images
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You know that person in a group of friends who's always, always, always dating someone, to the point where something might be a little wrong with them? Yeah, I'm that person. I did the math recently and I've spent a third of my time on this Earth in serious long-term relationships.

As something of a next-level serial monogamist, I've experienced more than my fair share of breakups, mostly scattered across four U.S. cities: New York, N.Y.; Princeton, N.J.; San Antonio, Texas; and now, quite recently, San Francisco.

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Media: Kiley Roache, Elizabeth Gerson

Even though the SF breakup was the most mature, mutually compassionate and adult I've ever had, it was still, holistically speaking, also the absolute worst.

Slogging through the aftermath pointed me toward one glaring, admittedly hyberbolic conclusion: San Francisco is the most annoying city in America in which to end a relationship.

Click through the gallery above to read why

ALSO: Is SF a hotspot for singles? WalletHub says yes

Why stay, if San Francisco makes life's transitions so much harder? It's a hard question.

We all have complicated relationships with this city — its dysfunction, its challenges, its many wild beauties. There's lots to love here, lots we want to fix and more we do not want to lose. Leaving is always bittersweet.

Filipa Ioannou is an SFGATE staff writer. Email her at fioannou@sfchronicle.com and follow her on Twitter