My Awkward Sexual Adventure (2012) on Netflix

Plot summary

Jordan Abrams, a conservative Jewish accountant, lives with his girlfriend Rachel Stern. The night before an extended vacation on which he planned to propose, Rachel tells him she cannot marry him because of his sexual ineptitude. His friend Dandak advises him to visit a strip club, where Jordan meets Julia and buys her chips. He drinks too much, is thrown out and robbed of his pants. Julia brings him to her apartment, and in the morning he sees her papers showing a large debt. He recruits her as his teacher in exchange for managing her finances.