Lovely, Still (2008)

As Christmas is approaching, Mary moves in with her daughter Alex/Elizabeth Banks across the street from old, lonely Robert/Martin Landau. Robert works at a supermarket. He meets Mary/Ellen Burstyn when she drops in to check he's OK after seeing his car crashed into the garage. She later invites him out for dinner date, letting him pick the restaurant. Robert asks his colleagues for advice on dating as it's new to him. Manager Mike/Adam Scott helps him out more than once. The date goes well despite Alex's worries and is followed by other dates.