30 Love (2009)

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.

A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.

A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.

A novelist's longstanding marriage is suddenly upended when she overhears her husband giving his honest reaction to her latest book.

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.

A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.

The owner of a factory that produces flavor extracts, Joel Reynold seems to have it all, but really doesn't. What's missing is sexual attention from his wife, Suzie. Joel hatches a convoluted plan to get Suzie to cheat on him, thereby clearing the way for Joel to have an affair with Cindy, an employee. But what Joel doesn't know is that Cindy is a sociopathic con artist, and a freak workplace accident clears the way for her to ruin Joel forever.

The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of Manhattan, but as he jumps from one lavish party to another and engages in numerous empty romances, he starts to doubt the worth of his work. Meanwhile, top TV producer Tony falls for Robin and introduces her to the world of celebrity.

Suzanne Stone wants to be a world-famous news anchor and she is willing to do anything to get what she wants. What she lacks in intelligence, she makes up for in cold determination and diabolical wiles. As she pursues her goal with relentless focus, she is forced to destroy anything and anyone that may stand in her way, regardless of the ultimate cost or means necessary.

She's a magazine writer who gives up her career for love and family. He's a playboy newspaper columnist who can't quite give up his old tricks. And if that combination doesn't give a relationship heartburn, nothing will.