Jerry’s Girl

Tucked into a booth at La Goulue on a recent, balmy afternoon, enjoying delicate bites of salmon, Thayer Iaccaci, age

Tucked into a booth at La Goulue on a recent, balmy afternoon, enjoying delicate bites of salmon, Thayer Iaccaci, age 66, looked the very picture of a Grand Dame of Madison Avenue. She wore a colorful yet conservative Miu Miu dress, black patent-leather Jimmy Choo’s and gold hanging earrings. Her hair was in a tasteful bob and her posture was perfect.

Only when she opened her mouth and in her soft, quavering voice said, “It wasn’t just the music, it was everything about it. Just to know that if you go somewhere on a certain date, at a certain time, you’re just going to be blissed out for a few hours, that’s pretty nice … ” does her lunch companion remember that this elegant woman was Jerry Garcia’s sporadic lover for more than 20 years. “He was really just a great friend,” she said of the Grateful Dead’s leader and guru to millions of twirling, passionate fans. “Only, we did kick our relationship up a notch between marriages.”

Ms. Iaccaci grew up a long way from Haight-Asbury—the leafy lanes of Darien, Connecticut, to be precise. Her parents sent her to boarding school when she was 6. “That was the start of a bad taste in my mouth for boarding schools,” she said.

There would be 12 more boarding schools. “I’d run away, come home, and then they’d send me to another one,” she said of her parents. “They never really got it—until finally they decided that I was out of my mind, so they sent me to a mental institution in Connecticut—where, thankfully, I ran into a wonderful doctor who told them that there was nothing wrong with me, that I just wanted to be home, and just to send me to a school near home.”

At which point the Iaccacis decided to send their 17-year-old daughter to a school in Europe.

Ms. Iaccaci’s life from that point zig-zagged about the globe. At 18, she moved in with some girlfriends in the New York City and worked retail, then spent three years in Florence, where she worked as a model for Emilio Pucci. There were the occasional visits to the family compound in Ecuador: Ms. Iaccaci’s grandfather built railroads there. It was there, in the port city of Guayaquil, that she met her first husband, whom she married in 1964.

Cut to three years later: the summer of 1967, the so-called Summer of Love, and Ms. Iaccaci was a divorced, 27-year-old single mother of a 3-year-old son living in a $300 per month two-bedroom apartment on the Upper East Side.

But not for long: the sweet sounds of free love reached Ms. Iaccaci one day on a walk through—where else?—Central Park.

“It was right over there,” she said on a recent stroll, pointing to a path near the reservoir. “It was the most beautiful sound I’d ever heard.”

The sound was the strumming and harmonizing of two hippie dudes, who soon took up residence in her apartment. Soon enough so many like-minded folk were crashing on her floor, Ms. Iaccaci and her son Nicholas moved in with a woman named Ronny Keith, who lived on a houseboat/animal shelter off Staten Island. Ms. Keith was a herpetologist, and the boat’s residents included a caoti mundi, a boa constrictor and chimpanzee named Samantha.

It was there that Ms. Iaccaci met Cosmo, “my first hippie boyfriend.” In the fall of 1969, after attending Woodstock and her first Grateful Dead show, Ms. Iaccaci and Cosmo and Nicholas headed west.

“Cosmo and I refurbished a Volkswagen bus and we took off, waving goodbye to my mom at the Colony Club at Park Avenue and 62nd street,” said Ms. Iaccaci. “Oh, the look on her face! Just so horrified, like, ‘Oh, no.’”

Jerry’s Girl