Roger Swanson is convinced he's a modern day Casanova. With his razor sharp wit and silver tongue, the New York ad man believes he can talk any woman he wants into bed. So, when his 16-year old nephew, Nick, comes to town looking to lose his virginity, it's no surprise that he turns to his Uncle Roger for a few lessons in the art of seduction. Rising to the challenge, Roger takes his teenage protégée on an all-night crash course on how to "close the deal". But as the evening unfolds and the pair move from singles bar to exclusive Manhattan party and beyond, Roger, the once irresistible Romeo, slowly begins to realize he may be losing his touch...