Up in the Air (2009)

An idea from a young, new co-worker (Anna Kendrick) would put an end to the constant travel of corporate downsizer Ryan Bingham (George Clooney), so he takes her on a tour to demonstrate the importance of face-to-face meetings with those they must fire. While mentoring his colleague, he arranges hookups with another frequent-flier (Vera Farmiga), and his developing feelings for the woman prompt him to see others in a new light.