Sayre Piotrkowski and I were having dinner at the St. James Brasserie the other night, talking about the things that we always talk about: music, beer (he’s a certified cicerone), the futures of San Francisco and Oakland and, of course, relationships. Like so many of my close friends, Sayre lives in Oakland, so we don’t get to catch up on each other’s lives as much as we’d like.

“We’re living in a really incredible time,” he told me while digging into a mussel. “We’re seeing the breakdown of so many things. The generation younger than us will take things like polyamory, gender-fluidity and having kids with a longterm partner you’re not married to as givens.”

“Even though the Bay Area seems to be ground zero for all that,” I said, “I’m still trying to learn all the new rules.”

Being 35 and newly single is a funny thing. Even though it’s only been a couple years since the last time I was single, it really does seem like every time I get out of a longterm relationship, I have to learn a bunch of new rules. The question though is whether it has to do with shifting cultural mores or my age — or both.

Last time I was single, Tinder was brand new and it revolutionized the way people met. You could be sitting on your toilet and connect with someone you might bang later that day. This time around it feels more and more like people are aching for real-life encounters. So many people I talk to complain that they are sick of dating apps. That’s why when I teamed up with #HellaFunny to throw a comedy show and dating mixer. We had a few hundred people show up despite it coinciding with a Warriors playoff game. I think the same thing will happen on June 30, when we throw our next Hella Single party at Milk Bar.

San Francisco is a small town, so it’s nearly impossible to go somewhere without running into someone who’s seen you naked. And partially because of this, the line between friend and lover is often hard to define. But what I’m often finding now is that, from polyamory to open relationships to “my shit is complicated,” it seems more common than ever that San Franciscans are experimenting with non-monogamy.

And it’s not who you’d expect either. I mean, sure, I turned down a possible orgy last weekend that may have included a few people dressed as clowns, but those are the folks who’ve been doing the polyamory thing for years. What’s new is that I meet women who look like typical Marina girls who are in polyamorous relationships as well.

It’s a fascinating and exciting time to be single … I think.

The hardest part about having so many options is deciding what it is you actually want. There’s the part of me that does want to meet someone soon and settle down to have kids and a more traditional home life. While there’s another part of me that wants nothing more than to have a few casual partners where my only responsibility is to be with them when I’m actually with them. While I don’t know what the answer is right now, I have a feeling it’s gonna be a fun and interesting time trying to figure it out.

Stuart Schuffman, aka Broke-Ass Stuart, is a travel writer, TV host and poet. Follow him at BrokeAssStuart.com. Broke-Ass City runs Thursdays in the San Francisco Examiner.Broke Ass CityBroke-Ass StuartgenerationOaklandRelationshipsSan FranciscoSayre Piotrkowskisingle lifeStuart Schuffman