‘Dating Ourselves’ Has Special Ring of Truth for Its Authors

Talk about taking the leap.

Would you schedule your marriage and the premiere of your first play--in which, by the way, you’re also performing--within a month of each other?

Writer-performers Rachel Winfree and Michael Caldwell never actually planned things this way, but if their years traveling the comedy circuit of the American heartland taught them anything, it was that plans are made to be rewritten. When it came, though, to their life--and their play, “Dating Ourselves,” opening Thursday at Theatre/Theater in Hollywood--everything had to be rewritten.

To begin with, the couple were merely drawing up character sketches last October for the next show of The Hilarions, their ongoing comedy troupe whose most recent piece of rapier-like lampooning was “The 27th Annual PLATE Awards,” spoofing both small towns and awards shows.

But, as characters are wont to do, they changed into the Reynolds family, and “Dating Ourselves” was born. A mid-January opening at Theatre/Theater looked likely.

After seven years together, Winfree and Caldwell started talking marriage. OK, after the run of the show.

Theatre/Theater, though, had too many shows doing too well and extending too far into the future for an available slot for “Dating Ourselves.” Later. Spring, maybe. In the meantime, rewrite.

Then, the Big Event meant streams of the couple’s Texas-based relatives pouring into town. Clearly, only a three-day holiday weekend would provide the room and time for an affair becoming as big as, well, Texas. Their wedding took place Memorial Day.

How about late June? Theatre/Theater artistic director Jeff Murray asked Winfree and Caldwell regarding the show’s opening. Not exactly optimum scheduling, but after all the delays, the duo could hardly postpone.

It’s all part of the When-You-Least-Expect-It Syndrome of “Dating Ourselves,” which tracks the Reynolds parents and children--12 total, all played by Winfree and Caldwell--from the end of World War II to the near future, or as Caldwell says, “the day after tomorrow.” A kind of baby boomers epic, the play reflects for Winfree how her generation has grown up in a challenging time. “Things haven’t ended up at all the way that we thought they would,” she says.

She pauses, then continues in her muted Austin twang: “I was the youngest in my family, and by the time I was in my teens, my father was doing financially better than ever. He thought I deserved it all; I was kind of put on a pedestal. From that vantage point, you just imagine a constantly brighter tomorrow with endless possibilities.”

The unlimited warranty on the American Dream, though, has run out for a Vietnam generation filled with many who can’t manage to muster the down payment on a house, or afford a child, or save for the future. But, as the couple talked about the darker shades of their first comedy-drama in their newly occupied Beachwood Canyon apartment, they refused to see the course of the Reynolds--or their peers--as a downhill slide.

“No,” Caldwell says, “this is a story about moving on. We’re the sum of those who came before us, plus some extra ingredients.”

Winfree and Caldwell know all about moving on. Call it storybook, call it nice-sounding PR, but they insist that they were friends and artistic partners from the day they met in 1985--when Caldwell tried out for an Austin improv group that included Winfree. “He was on stage that night. I mean, he had it ,” Winfree recalls. What the two of them had, together, was a symbiosis, feeding off each other’s comic intuitions. Shortly after, the bottom fell out of the Texas economy and, Caldwell notes, “the first things to go were comedy clubs.” They decided to take their symbiosis on the road.

As the senior member of the twosome, Winfree had already spent 10 years gaining degrees at the University of Texas at Austin: Her masters in children’s theater included two published plays, “I Didn’t Know That” and “Flashback.” She affectionately notes that “Austin can be the country’s best retirement home for the young,” and while she tried a less-retiring life in New York, she returned home in 1980 to work in Austin’s new performing arts center. So, it was natural to later pull up stakes and travel the club circuit with Caldwell.

“We turned over the car’s odometer two times,” he says, “driving all over the place, especially the Midwest. “

“We were the happy travelers,” Winfree giggles, “but there were some nightmare gigs that pretty much drove us back into the theater.”

Besides, why bother with clubs? Friends were telling them then what they tell them now: That their work gravitates toward theatrical stylization and away from the presentational stand-up or a skit’s simple cartoonishness.

“What’s so striking about Michael and Rachel is that they do it all: costuming, writing, acting,” says their director, Bill Molloy. “I’m intrigued by the script’s epic reach across the decades. But more than anything, they’re two dedicated people who are actually doing this and not just talking about it.”

“A family, with a history, was forming before our eyes,” says Caldwell,”and we realized that we had a real play. A difference between this and a Hilarions show is the shaping, and Bill greatly helped. We have, for example, family members talking at the beginning about dating, but in 1940s terms of what to do for the girl, how to open the door for her and so on. At the end, dating rules come up again, but now it’s the ‘90s and the talk is about AIDS.”

Winfree goes further: “While writing this, Michael and I were talking about our own values, our families, and we started talking about marriage. I was reluctant to change, but Michael was insistent on marrying. The writing--and Michael--finally broke down all those silly defenses of mine. I mean, I never wanted to marry!”

“Dating Ourselves” plays at 8 p.m. Thursdays through Saturdays and 7 p.m. Sundays at Theatre/Theater, 1713 N. Cahuenga Blvd., Hollywood, starting Thursday and ending July 26. Tickets: $12 to $15. Call (213) 960-5596.