Love, Sex, and Missed Connections (2013)

Missed Connections is a comedic romance about a guy named Neal who finds himself knee-deep in a quarter-life crisis. He is haunted by the memory of catching his best friend and girlfriend having sex with eachother. After quitting his job and suffering through the worst birthday party of his life, he tries to get over his ex by doing what anyone would do tricking women on the Internet. At the suggestion of his two real best friends, Barry and George, Neal sets up fake dates with women who have placed Missed Connections ads online. He goes on the dates but only watches from a distance as the girl waits for someone to show up. Just as the girl is about to leave, Neal comes over and tells her that he wouldn't have stood her up. Checkmate. Neals plan is going really well, until he meets Jane and then keeps meeting her. As it turns out, Jane may be just as damaged and devious as he is.

Source: TMDb