The Merry Gentleman

The Merry Gentleman is a 2008 drama film directed by Michael Keaton in his directorial debut, and starring Keaton and Kelly Macdonald. It is about a woman who leaves an abusive relationship to start a new life in Chicago, where she forms a friendship with a hitman who is undergoing his own emotional crisis.

One night, she is seen in an office window through the rifle scope of professional hit man Frank Logan, who is on the roof of the opposite building, as he prepares to shoot the occupant on another floor. Afterwards, rather than leaving, he removes his hat and steps out on to the ledge as he apparently prepares to jump. As Kate steps out onto the sidewalk, she looks up at the falling snow and sees Frank on the ledge. She cries out, startling him into safely falling backward onto the roof.She decides to bring a small bit of joy to her life by buying a Christmas tree. Later that night, she encounters Frank at her apartment building. She doesnt recognize him as the man on the roof, and he helps her carry the big Christmas tree to her apartment. He later returns to meet with her, but collapses from pneumonia before he can reveal why hes there. Kate rushes him to the hospital, and despite the awkwardness of their conversation there, they develop a friendship that has hints of romance. Some time after his release, she mentions the old hat that he wears wonders about the things it has seen, unknowingly referring to the many men that Frank has murdered. Meanwhile, Kate also becomes the romantic interest of Murcheson, the detective investigating Franks latest murder. Murcheson asks Kate out to dinner, but she mistakes the date for a meeting about the investigation, and cuts the date short when she realizes Murchesons romantic interest. ........

Source: Wikipedia