You're searching for the 2010 film My Girlfriend's Boyfriend, starring Alyssa Milano. Jesse presents herself to Ethan, a struggling writer, in a moment of brash confidence. Then [wealthy ad executive] Troy steps in and presents himself to Jesse with brazen confidence. She picks him. The movie is based on a real relationship. It tells the story of Jesse, a young woman who has just been fired from her job. Hoping to find another waitressing job, she goes out on her bike and ends up at a party where she meets E/thane. They talk all night and when morning comes, she realizes she's made a big mistake by leaving her apartment behind. Now she feels guilty because she knows he needs a job too. So she asks him if he would be willing to move in with her, but he says no, because he needs his own place. However, he does give her advice about finding another job. Later on that day, she gets a call from a friend who wants her to meet her at a bar. When Jesse arrives, she finds out that this friend works at the same restaurant where she used to work before she met E/thane. The owner offers her the job again, so she takes it without even telling E/thane. This time she doesn't feel guilty at all because she knows he will be happy when he finds out that she got another job.