20 Dates by Myles Berkowitz is a charming little pseudo-documentary about what happened when the author, an impecunious independent filmmaker, unexpectedly got $60,000 to produce a film “combining my two biggest failures, my personal life and my professional life.” His gimmick is to be his own star and to go out on 20 dates, recording them on film as a kind of chronicle of courtship in the nineties. Interspersed with the dates are conversations with a “film expert” called Robert McKee (a former teacher), who comments on classic celluloid romance, with his skeptical agent, with Elie, his extremely shady and foul-mouthed financial backer (whose face we never see) and with various friends and acquaintances who tell us what a schlemiel he is. At one point he asks his friend, Barbara, “Do you think I piss off a lot of women?”
Barbara thinks for a moment and then replies: “I wouldn’t narrow it to a gender thing.”
It is hard not to be charmed by such self-depreciation, or by a man subject to so many disasters, romantic and otherwise. Part of the problem is of course the cameraman he takes with him on his dates. When he tells Tracy about it, she says: “Do you think that you’re going to find love when there’s a camera two feet from your face?” — adding (not inaccurately) that his film isn’t really about dating at all. “It’s all about you, isn’t it?” When he keeps the camera hidden from Karen and Christian, they sue him. One date excuses herself to go to the ladies’ room and never comes back; another one orders for dinner a three pound lobster that Berkowitz can’t pay for. The boyfriend of a third surprises them in the restaurant and threatens to beat him up. He gets the brush-off many times. “You mean you don’t know what your type is but you know I’m not it?” he asks one woman.
“Yes,” she replies.
Not too surprisingly, we don’t really learn very much about contemporary courtship that we did not already know. Elie, who wants him to put Tia Carrere into the movie and show some t*** and a*** — which is what “sells” — says: “Let me give you a piece of advice about love: love don’t f****** exist.” But then again maybe it does. One of the 20 dates turns out to be molto sympatico, and soon she and Myles are seeing a lot of each other. Then comes the problem of jealousy as he insists on finishing his film — that is, going on a number of dates with other women, even though he wants to build a relationship with this woman. They quarrel. Berkowitz, apparently to bolster his side of the audience interviews “Some Kid” on camera, a little girl for whom his situation is translated as a boyfriend who wants to go to his Little League game instead of being with her. The girl answers: “If he has a girlfriend and he cares more about baseball, that’s stupid.”
What else is there to say? It turns out that the film isn’t really about the nineties but something more permanent. There is a whimsical but happy ending as Myles and his new lady love walk away from the camera, hand in hand. “Love is like a really great movie. . .you’ve got to catch it,” he says. And then: “Did you expect music?” And so there is music. Such stuff is very light but very digestible.