"I'm looking for my Annie Hall," says the lovelorn 35-year-old, whose new short film, "Get the Script to Woody Allen," is as concerned with his dating mishaps than his desire to be famous.
Beginning this and every Thursday in August, Black's short will screen before showings of classic Allen films at the Loews 34th Street Theatre.
As the movie opens, Black (who wrote, directed and stars) is on a tense first date, which quickly disintegrates when he whips out coupons to pay for dinner - a trick he says he often uses in real life.
"The coupon thing is so controversial!" says Black, whose friends have begged him to stop.
But he says any woman who has a problem with thriftiness isn't for him.
"The girl that's for me is street-smart - she doesn't care if I use coupons," he insists. "Look at this economy!"
Though the film has a happy ending - he meets a woman who is even more neurotic and insecure than he is - Black says he's still looking for his match.
"My therapist is my dating coach - and he's going to be 91," says Black.
"He gives me rational advice - to train yourself to not take rejection so seriously, to stop worrying what people think of you."
He says it's helped him to be as assertive with women as he is about publicizing his movie.
"These are all things I talk about on my dates," he says. "I'll brag about my low self-esteem. I'm like the heartbreak kid. Women are so charmed by it."
His next script, "Romantically Challenged," is also about an unlucky-in-love guy who finds a mentor to help him seduce women.
Black, who plans to pitch it to major studios, says he will play the lead. "The only actor I would let take my place is Jack Nicholson or Denzel Washington," he says.