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You Can’t Spell San Francisco Without a Few Exes

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This originally appeared in my Broke-Ass City column for the San Francisco Examiner. It runs every Thursday.

You can’t spell San Francisco without a few exes. From the person you had a one-night stand with six years ago, to the one who suddenly stopped texting you after dating for a couple months, to the person you loved so completely that it nearly broke you: Running into people you’ve been involved with is an inevitability. San Francisco is for lovers — especially ex ones — and I’m having a very San Francisco week in that regard …

By complete coincidence, I’m hanging out with two of my three serious ex-girlfriends this week. I met Tia on the 71 bus when I was 21. I was just in The City for a summer internship when she walked onto the bus and into my life. We were together for three-and-a-half years after that day. That was a very long time ago, and now she’s more like a family member than anything else.

We got drinks at the Hemlock Tavern the other night and caught up on each other’s lives. She told me about her new boyfriend, what hijinks her many family members were up to and how she was within a year of having her Psy.D. I regaled her with my weird stories of what it’s like dating in your mid 30s. We laughed and drank and talked about what it meant to be so young and in love, like we were 15 years ago. We were insane people back then.

Later this week, I’m grabbing lunch with Krista. She and I dated for nearly five-and-a-half years and lived together for most of it. We met at the Power to the Peaceful Festival in Golden Gate Park, when that was still a thing, and fell deeply into each other for the next half-decade. We had one of those very S.F. breakups, where you still have to live together for a few months because neither can afford to move out.

She recently got married to really great fella named Anthony. This will be the first I see her in awhile, and I’m excited to congratulate her in person and hear all about the wedding.

When you’ve been here for awhile, your history is speckled on intersections and street signs all over town. Restaurants you went on dates to, bars where you argued drunkenly outside, corners where you stopped, held hands and kissed as the fog and wind whipped down the street. If you don’t come to terms with the ghosts of your past, they will haunt you through every boulevard and avenue in The City. Luckily, it just takes a little time and eventually you can be friends with the people who, many years ago, were so much more.

My most recent ex moved to Chicago shortly after we broke up. As anyone who has ever survived a San Francisco breakup knows, you spend the first few months hoping desperately not to run into your ex, especially if they are out with someone else. This is the first time I haven’t had to worry about that. I’m not gonna lie, it’s made the transition a bit easier … for me at least. I imagine her transition to a completely new life 2,000 miles away wasn’t nearly the same. And that’s too bad because when you really care for someone, all you want is for them to be happy, and I hope she is.

You may not be able to spell San Francisco without a few exes, but I wouldn’t want it any other way. Touching base every once in awhile with the people who helped shape who you are today is often the best way to remember who you were back then.

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Broke-Ass Stuart - Editor In Cheap

Broke-Ass Stuart - Editor In Cheap

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.