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On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?

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.

A fidgety, wisecracking video store clerk develops a fixation on a particularly reclusive customer, a frequent visitor to the pornography section of Cinefile, the video store where he works in Los Angeles. After multiple failures to impress her during their brief daily transactions, he finds her street address in the store's database, drives to her apartment building and initiates an unconventional campaign to win her affections.

College "frenemies" Lauren and Katie move in together after losing a relationship and rent control, respectively. Sharing Katie's late grandmother's apartment in New York City, the girls bicker with each other until one fateful night, when Katie's noisy bedroom activities make Lauren barge in and discover a dirty little secret. This revelation brings them closer together, and Lauren (the brains) and Katie (the talent) concoct a wildly successful business venture. As profits swell, the girls reevaluate their hopes and dreams and realize that just because someone pees in your hair in college doesn't mean she won't be your best friend 10 years later.

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

How far would you go to get the person of your dreams? With the help of Gwen and Tiffani, Kyle pretends to be heterosexual in order to land Troy, the new guy (and nude model) who's turning the heads of both men and women. He soon finds himself joining the campus ex-gay support group and nabbing a girlfriend! Kyle's ex-boyfriend Marc is horrified at the plan and decides to pursue the confused Troy with his own tactic -- being his "out" gay self. Who will win Troy first?

In a Paris hotel room, Jack Whitman lies on a bed. His phone rings; it's a woman on her way to see him, a surprise. She arrives and the complications of their relationship emerge in bits and pieces. Will they make love? Is their relationship over? (A prequel to The Darjeeling Limited, 2007.)

Two lifelong friends navigate complex sexual encounters and emotional entanglements, wrestling with societal norms and personal desires.

Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.

Restless and unhappy, two couples get caught up in infidelity and deception. Barry is a sullen businessman married to Mary, a writer who is unsatisfied with their relationship. Mary begins an affair with Jerry, a smug theater professor and husband of her friend, Terri, who is also a writer. Adding to the adulterous mix are Cary, a callous doctor, and Cheri, an art-gallery assistant.

A young sex worker from Brooklyn gets her chance at a Cinderella story when she meets and impulsively marries the son of an oligarch. Once the news reaches Russia, her fairytale is threatened as his parents set out to get the marriage annulled.

With high school a distant memory, Jim and Michelle are getting married — and in a hurry, since Jim's grandmother is sick and wants to see him walk down the aisle — prompting Stifler to throw the ultimate bachelor party. And Jim's dad is reliable as ever, doling out advice no one wants to hear.

The life and career of shock-jock superstar Howard Stern is recounted from his humble beginnings to his view from the top. Possessing a desire to be an on-air personality since childhood, Stern meanders through the radio world, always with his supportive wife, Alison, by his side. Landing a gig in Washington, D.C., Stern meets Robin Quivers, who will become his long-time partner in crime. When the two move to New York, they face the wrath of NBC executives.

New York comedian Alvy Singer falls in love with the ditsy Annie Hall.

Hallam's talent for spying on people reveals his darkest fears-and his most peculiar desires. Driven to expose the true cause of his mother's death, he instead finds himself searching the rooftops of the city for love.

When his girlfriend leaves for New York City on a 3-month-long internship, a strongly opinionated Berkeley arthouse movie theater manager begins exploring life as a bachelor.

Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.

Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses and parents, Elliot is a perfectly nice guy. And that's his problem.

At a sizable public college, high-minded student Eddy is forced to room with the slovenly Stuart, but the pair strike up a surprising friendship. When attractive co-ed Alex is assigned to live with the two male students because of her gender-neutral name, a roundabout love triangle ensues. Eddy secretly yearns for Stuart, who wants Alex, but she prefers Eddy. The complex situation leads to sexual experimentation and strained relationships.