By following ten simple rules, 20-somethings Vince and Cameron spice up their relationship by sleeping around. But when their straitlaced friends get engaged, their relationship gets turned upside down. To put the rules to the test, they will go on the road to the Hamptons to crash the biggest party of the year where love triangles collide and off-the-wall mayhem ensues.

Three years ago, Walter and Nadia began what seemed to to be the most unusual relationship. Getting used to the 17 year age difference was a struggle for Walter. A big struggle. All is well, until Walter's niece moves to Atlanta and falls for, Tank, Walter's womanizing, best friend. Everyone decides to keep the romance a secret. But when Walter finds out he finds himself, just being Walter.

When 43 year-old Walter and 26 year-old Nadia met, he wasn't looking for her, and she wasn't looking for him. Now that they are together, nobody can believe it. At times neither can they. To Walters' friends she's a one-night stand. To Nadia's friends he's a sugar daddy. Both find themselves trying to prove to their friends that their relationship is real. While Walter struggles with the relationship because of the difference in age, Nadia embraces it wholeheartedly. Ultimately they find that they've spent so much time convincing the world that their love is true, they must now convince one another.