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A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.

Four tales unfold in the Eternal City: While vacationing in Rome, architect John encounters a young man whose romantic woes remind him of a painful incident from his own youth; retired opera director Jerry discovers a mortician with an amazing voice, and he seizes the opportunity to rejuvenate his own flagging career; a young couple have separate romantic interludes; a spotlight shines on an ordinary man.

Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a suitable match for his boss. Despite their mutual attraction, Cathy and Philip want different things. Philip wants a fling, while Cathy wants a marriage. As they travel to exotic locales, their differing motivations are put to the test.

Tom has plans to take a nice long nap in a hammock, but Jerry has gotten there first and is snoozing happily, so the two fight it out to see who gets to sleep there.

When a woman crashes at an empty Italian villa, posing as the owner's fiancée, she discovers an unexpected romance that could transform her life.

A head injury causes a woman to develop an extraordinary amount of confidence and believe she's drop dead gorgeous.

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.

Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?

Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

When a hypochondriac assumes that he is dying, he makes an elaborate plan to ensure his wife's happiness. However, trouble ensues when she misunderstands his intentions.