Pssst: Jewish woman takes her dating adventures onto stage

Like most people in the known universe, Caylia Chaiken has been on a few bad dates.

Unlike most of us, she made a one-woman show out of them.

“Caylia Chaiken: The Date Whisperer” is one part comedy, one part musical theater, one part group therapy — all of it based on her dating adventures over the past few years, as someone beyond her 30s. Her first performance of 2012 will be on Jan. 28 at the Showcase Theatre at the Marin Center in San Rafael.

“There are so many things that just get stickier about dating when we’re older, especially online,” says Chaiken, a lifelong singer and performer who also gives private music lessons in Marin.

Caylia Chaiken

“You revert back to high school in many ways. You’ll be nervous about the kiss-at-the-front-door type of situation after a first date, but you don’t know if he’s an ax murderer, so you meet in a public place instead of your house, and then instead of the front door you’re standing in a parking lot with overhead lighting and a security car driving around.”

Chaiken created the production with her longtime friend and collaborator Jennifer E. Hewitt. Packed with energetic musical numbers, it tackles the full range of awkwardness presented by dating in the modern age: speed dating, singles events, matchmaking websites and more.

“Speed dating is hysterical, because you have five minutes to decide if you click with someone,” Chaiken says. “I don’t know about you, but I can’t figure out what to wear in five minutes. And I have an unusual name, so that’s a good minute …”

Jewish culture and humor infuse many of Chaiken’s anecdotes. For example, there’s the story of how her parents tried to create a shidduch when she was younger by inviting a family from their synagogue — including their single son, of course — over for Shabbat dinner. “The thing is,” Chaiken notes, “we had never observed Shabbat before that night!”

And the Internet hasn’t exactly made Jewish dating simpler, she adds. “Jdate is like 31 flavors — there are so many varieties of Judaism. There’s East Coast vs. West Coast. I even see a difference between Southern and Northern California Jews.”

Born in Southern California, Chaiken grew up in Pittsburgh. Encouraged by her parents, she played piano beginning at age 5, but didn’t start singing until a few years later.

“I didn’t realize I was a singer until my bat mitzvah, when, after I sang, people shouted ‘encore!’ instead of ‘amen,’ ” she says. “No, really.”

She moved to San Francisco to attend the Conservatory of Music following high school, received another degree in music and theater from San Francisco State University, and set about working as a cabaret singer at venues throughout the city.

Along the way, she married her college sweetheart, a partnership that lasted 10 years. When it ended, it also dissolved some illusions for Chaiken. In a song about taking off the “rose-glass slippers,” she blames the Brothers Grimm for perpetuating the idea of a Prince Charming.

However, she says, staying hopeful and upbeat about dating — and about life as a single person — is a central message of the show. She believes that “love is all around us — it’s cheesy but I believe it’s true. That’s what keeps me from getting cynical.”

Reactions to the show, which Chaiken has performed three times previously to capacity crowds of 300 at the Marin Center’s Showcase Theatre, have been overwhelmingly positive, she says. People often tell her they leave feeling better about themselves.

“I’m not a therapist, but I am sensitive, and I’ve experienced a lot. I know people,” she says. “And I find that by telling my story, people realize they’re not alone, and they tend to open up.

“Some of the singles events I would go to, maybe I wouldn’t meet a guy, but I’d wind up making friends with other women there,” she continues. “You realize that while dating brings out all of our insecurities, most of this stuff is so universal. If we can shed a light on some of it, and be lighthearted about it, we can start to heal a little. And hopefully have a good laugh while we’re at it.”

“Caylia Chaiken: The Date Whisperer,”
8 p.m. Jan. 28 at the Showcase Theatre–Marin Center, 10 Avenue of the Flags, San Rafael. $25. or (415) 499-6800.

Emma Silvers

Emma Silvers is a former J. staff writer.