"So I decided to combine my two biggest failures: my personal and my professional life," says Berkowitz, now 36.
The struggling director hired a cheap cameraman and clandestinely videotaped himself going out on 20 dates.
The result is his ultra-low-budget mockumentary, "20 Dates," the winner of the Audience Award at the 1997 Slamdance Festival. It's a cross between "Singles" and "This Is Spinal Tap."
Except all the dates are real.
On one outing, the recently divorced Berkowitz, who is scared of heights, bungee-jumps to impress a sexy blond named Shalimar. On another, the good-looking but annoying director is ditched by a woman who excuses herself from the table, never to return. Berkowitz has to dodge a date's stalker ex-boyfriend (he makes a hasty exit via the restaurant's back door). And when a feminist ballerina spies the hidden camera, she stabs Berkowitz in the arm with a fork.
Halfway through the movie, Berkowitz has accrued two lawsuits, several stitches in one arm, and the wrath of his producer, a foul-mouthed, Lebanese-born huckster named Elie.
"He thought that if I went out on 20 dates, there would be a lot of sex and nudity, and that he would be able to sell the movie in Europe and make his money back," says Berkowitz, who secretly taped his meetings with Elie by hiding a tape recorder in his briefcase. "Elie wanted T and A. So he was absolutely horrified when he saw the raw footage of my first few dates. He couldn't believe that a guy could be so incompetent with women."
Many of Berkowitz's dates look like a scene from an Albert Brooks movie. In the film, Berkowitz also interviews several of his friends, who refuse to set him up with women. He pays a visit to his ex-wife, who derides his bedroom skills. He concurs with a woman who says, "Being single in L.A. is like being a cinder in hell."
Then the unexpected happens: A gorgeous linen-shop clerk actually agrees to go out with Berkowitz on Date No. 9. "She's way out of my league," he says gushingly of Elisabeth, a UCLA interior design student. They fall in love on camera. But Elie won't let Berkowitz stop dating, and Elisabeth's patience begins to wear thin.
"I started out wanting to make a small, vicious movie about dating in L.A., but then things got out of control," says Berkowitz, munching a dry bagel during an interview at a West Hollywood cafe.
C'mon Myles, a reporter pressed during the interview. How much of "20 Dates" is really...real?
Berkowitz's response was a little cagey, but he assured that anything outrageous or too good to be true (i.e., Elisabeth) actually happened, on camera. His $60,000 budget allowed him only to use real woman as dates, not actresses. Berkowitz did restage certain scenes to "fill in the blanks" when necessary to complete his movie. But, then again, "20 Dates" is more of a "screwball romantic comedy" than a documentary, he said.
Berkowitz traces his dating ineptitude to his childhood in Pelham Manor, N.Y., where he was a funny, short schlemiel and one of few Jews in his entire school. He won Bible contests at the Conservative synagogue his parents helped found, but he wasn't a winner with girls. Berkowitz couldn't get a date until his sophomore year at the University of Pennsylvania, after he had completed a seven-inch growth spurt.
His parents were less than thrilled when their son, the Ivy League college graduate, bucked law school to try his luck in Hollywood.
Berkowitz was less than thrilled with his luck in Los Angeles.
He waited tables, did commercials for Coca Cola and Burger King, and wrote the occasional "Tales From the Crypt" episode for HBO. He won a Cable ACE nomination. But, he reckons, he mostly suffered "hundreds" of rejections.
One day in 1996, Berkowitz "looked in the mirror and realized I was a failure." The idea for "20 Dates," he says, was born of "pain and desperation." The humor in his movie, like all good Jewish humor, comes from suffering, he adds.
But "20 Dates" has a happy ending, like a fairy tale starring Woody Allen. Berkowitz tipped every cabbie and waiter in Park City, Utah, to help create a buzz about his movie at Slamdance. Fox Searchlight bought the movie not long after the first screening. And Berkowitz and Elisabeth, now 28, will wed in Hollywood in October.
In the editing room, "one of my female editors kept remarking: 'I've been out on dates with a lot of jerks just like you,'" Berkowitz says. "But now, I think of my film as a sort of public service announcement for true love. After all, if I can find it, anybody can."
"20 Dates" opens in Los Angeles on Feb. 26.