Kill Me Later (2001)

Selma Blair and Max Beesley play star-crossed lovers in Dana Lustig's KILL ME LATER. Blair is Shawn, a young woman struggling with her own self-negating romantic impulses. She's involved with a selfish married man (D.W. Moffett) who, completing the poor romantic choice trifecta, is also her boss. Early in the film, Shawn decides she has had enough misery. After a few suicidal gestures, she decides to take that final step and end her life. She goes to the roof of the bank where she works, and prepares to jump. Meanwhile a thief (Beesley) is concurrently in the process of robbing the bank, and when a witness sees Shawn perched on the roof and calls the police, she inadvertently foils the thief's plans. He takes her hostage, getting her cooperation only after he assures her that if she helps him, he'll repay her by killing her once they're free and clear. Naturally, things don't go exactly as planned.