Yes Man (2008)
Carrey plays Carl Allen, a Bank of America loan officer in Los Angeles whose life has shrunk into avoidance after his divorce. The premise is the structure.
Actor: Rhys Darby
Rhys Darby appeared in Yes Man and led Our Flag Means Death, and played the manager in Flight of the Conchords. He is a New Zealand stand-up and served in the army before comedy.