Tiffany, Charlie and Vernon are con artists looking to up the ante from their typical scams. They figure a good way of doing this is taking down Dean "The Dean" Stevens, a well-known cardsharp, in a rigged game. However, they first need enough money to enter a game with Stevens, so they decide to strike a deal with fellow crook Larry Jennings to scam a local gangster -- which turns out to be a bad idea.

Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.