John Mayer and I have what some would consider an unlikely friendship. He’s one of our greatest living guitarists, and I’m regarded as the dude that stirs the s— on late-night TV. We do have one thing that bonds us: our love of the Grateful Dead. So when the band did five shows this summer—their last ever—we used their Santa Clara, Calif., gigs as an excuse to take a road trip and bro it up.
On June 26, we made the journey up the 101 from Los Angeles. We were in John’s EarthRoamer off-road camping truck (which was v butch) and spent some of the drive pondering which of us was Oprah and which was Gayle (not v butch). Marriage equality had passed that day—and we were headed square into gay pride in San Francisco. I was on top of the world.
After an intense late-childhood Diana Ross fixation, I became a Deadhead. As a teenager in St. Louis, I’d drive in my ’72 Buick Skylark convertible to wherever they were playing and dance like I didn’t have a care in the world. Looking back, I wonder if Dead shows were my happy place because I was in the closet. As John and I were driving, I marveled at the notion of telling my scared teenage self that one day not only would I be out to all my friends and family—and, uh, everybody—but I would also be able to get married.
Once we arrived in the Bay Area, I took the dude who can make all the ladies’ panties drop to the Powerhouse (gay bars, FYI, always have v butch names). The vibe was jubilation mixed with intense body heat and plenty of disco (I explained Diana Ross to John). Did I mention a dude in a jockstrap assumed the role of our bodyguard? Anyway, John was the ultimate wingman, asking me who was tickling my fancy. As the night went on, we wound up on the dance floor and—from what I remember—it was nothing short of euphoric.
The next day, we moved from disco to the Dead. It had been 20 years since the group performed as the Dead (and 23 since I’d seen them), and I wondered: Would the crowd be all old yuppies? Am I an old yuppie? Would I still be able to dance like a free bird?
What I hadn’t expected was that when we wandered backstage, I found myself in the middle of a Real Housewives of Grateful Dead reunion, featuring Phil Lesh’s wife, Jill, and Bob Weir’s wife, Natascha. They knew as much about me as I did their husbands, and that was awesome. The audience was multigenerational and smelled just like GD concerts did in the day—a mix of body heat and pot (not unlike the Powerhouse). As for stronger stimulants, an insider told me night 1 was definitely the night to do psychedelics, so I took note. The band was tight, with Trey Anastasio playing Jerry’s parts. They began with “Truckin'” and “Uncle John’s Band,” and just before intermission, a rainbow appeared out of nowhere, and to put it bluntly: Everyone lost their s—. (Was it Jerry saying hi?) Backstage during intermission was equally surreal: There was Mickey Hart chatting up Nancy Pelosi, who was decked out in a white tunic. It seemed as much a mirage as the Jerry rainbow.
I spent the afternoon before the next day’s concert ogling pink poodles and leathermen at San Francisco’s robust pride parade. (I let John have the afternoon off.) Highlights of night 2 were “Hell in a Bucket,” “Sugar Magnolia” (my favorite), and “Brokedown Palace.” I spent most of the concert dancing furiously and gloriously, by myself, like I used to.
That weekend, the confluence of marriage equality, legalization of pot, and the Grateful Dead getting back together created a perfect combo platter, allowing me to do just what I had fantasized on the road trip: bring back my 19-year-old self to tell him it all turned out okay, and give him a big hug tied up with a rainbow. On the way home, a friend texted and said if I’d celebrated gay pride in any more of a straight way, I’d have had sex with a girl at the Super Bowl.
It was all epic and unforgettable—and I’m still celebrating.