My last trip to San Francisco was in 2000, when I drove down with Sharla Sava in my red Ford Tempo. Prior to that, a 1986 Green Tortoise odyssey that would be impossible now given the horrors of border security.

The San Francisco of 1986 still wore its activism on its sidewalks (I was there to protest Reagan’s foreign policy), while the 2000 version seemed drunk on dotcom speculation, turning the city from a site of critical engagement to one that catered to the whims of 25-year-old white heterosexual boys.

As for today’s city, what can one say after a three-day visit? The Beats and the Spicer Circle have long since left North Beach, while the intersection of Haight and Ashbury is rife with multinational coffee shops and clothiers. But that is to be expected. So where are the youth of today, besides flash mobbing in Union Square, their ear buds linked to “some DJ in Marrakech”?

“Valencia Street is where the young people are,” said Kevin, as we walked to dinner from a Bruce Boone reading. “Yes,” said Dodie, catching herself before suggesting that we go there during our one full day.

So we did, walking south from the 16th Street BART Station, past shops displaying decorative abstract paintings and new and used furniture, stopping now and then to check the menus of unimaginative restaurants, the non-ironic machinery of Dave Egger’s well-intentioned writing centre, infrequent bookstores, wondering what San Franciscan’s thought about, what mattered, and why?

Attempts to get at these questions, and more, were met with shrugs by the gallery director we dined with that night at Zuni’s. Are these questions not worth asking? I asked him, knowing as soon as I said it I would be met with another shrug. Would I be better to phrase my questions in the negative, as in, What doesn’t matter, and why not?

Before our evening flight, Judy and I decided to take a pass on the MOMA’s steep asking price (and dull program) in favour of the Jewish Museum’s Charlotte Saloman exhibition. The title alone was enough: Life? Or Theatre? Although yet another instance of a personality-driven event (in a country obsessed with them), Saloman’s project reminded me how fragile we are, how she was living at a time when asking the wrong question could cost you your life. Are we living in a similar time? Does it matter? And if not, why not?