Keith (Hugh Grant) was on top of the world – an award winning screenwriter, a beautiful wife and a seemingly inexhaustible supply of wit and charm. But that was fifteen years ago: now, he's divorced, broke, approaching fifty and hasn't written a hit film in years. Luckily, his agent has a job for him – a small town university is looking for someone to teach a course in screenwriting. Keith cannot believe it has come to this, but his attitude slowly begins to turn when he meets Holly (Marisa Tomei). A single mom working two jobs to earn her degree, the pair find themselves connected by their mutual need for a second chance.