Roommates (2009)

Loveable but awkward Mark stumbles upon his dream come true when he runs into his old high-school crush, Katie, and becomes her new roommate in an attempt to finally win her heart. Unfortunately for Mark, Katie is still in love with her on-again/off-again boyfriend. Further complicating matters, Mark doesn't hit it off with Katie's best friend and roommate, Hope, a strong willed television executive who Mark learns, unbeknownst to her fellow roommates, has lost her job and now secretly works at a coffee shop. The fourth and final apartment mate is James, who works in the investment world and takes great pleasure in watching Mark's feeble attempts to win Katie's favor. Rounding out the group is Mark's former roommate and best friend, Thom, a quirky guy who takes an instant liking to Hope.