Accidentally on Purpose (2009)

Billie, a 37-year-old newspaper film critic, is newly single after breaking up with her boss when a one-night stand with 22-year-old Zack leaves her unexpectedly pregnant. Choosing to keep the baby, she also decides to keep Zack in her life, inviting him to move into her apartment as they try to navigate an unusual new relationship with help, and complications, from their friends.