Charlie is a charming playboy who doesn't believe in serious relationships. His best friends bet him that if he sticks to one woman for one month, he's bound to get attached. Charlie denies this yet accepts the seemingly easy challenge, until he cross paths with the beautiful and mysterious Eva. They may agree to a casual affair, but eventually Charlie is questioning whether he may actually want more.

After being dumped by his model girlfriend, aspiring writer Quincy Watson quits his job and is inspired to pen the ultimate how-to book on breaking up. When it becomes a smash bestseller, he starts giving his player cousin, Evan, choice tips on how to win the battle of the sexes. After Evan's beautiful girlfriend, Nikki, utters the words "we need to talk", Evan panics and decides to leave her before she can leave him. But when Nikki realizes Evan's connection to break-up guru Quincy, it's these players that end up getting played.

Derrick is a struggling law student who takes a job as an awards show seat filler to make ends meet. One day, he is seated next to the beautiful pop superstar Jhnelle, who mistakes him for a well-known industry executive. With an instant chemistry, the unlikely pair begin to date.