It's How You Play the Game — Jimmy Gleacher

With a cinematic wit and some emotional insight (rare from the male perspective), Jimmy Gleacher delivers his debut novel, a clever and heartfelt tale of a twentysomething guy's trip through love and relationships.
Jack Wilson's got a few problems. First, there's his ex-girlfriend, Breach -- their relationship was too perfect for any twentysomething guy in his right mind. Unable to commit, he quickly ran the other way. Since then, the dating games have spun out of control.
Now there's his new girlfriend, Hope -- she's gorgeous, exciting, smart, and quite possibly crazy. Hope's rich friends? Even crazier. Jack's life is suddenly cluttered with young, beautiful people who have a strange definition of love. Relying on fate, Jack decides to ride the situation out with little or no regard for the consequences.
A no-good gambling father, the new girlfriend's psychotic mother, and a seductive older woman aren't making things any easier. Jack's getting plenty of advice, though. If he isn't seeking the counsel of the local Mafioso deli owner, then his mom and her "Friday Night Drinking Club" are more than willing to butt in. Through it all, Jack learns that finding love and living with it depends on a set of rules, a few good moves, and a dose of luck.