Ida, a beautiful mess obsessing over her marital separation, shows up at her sister Alison's for a visit a week too early. Alison is well used to cleaning up after Ida, and settles them both at a local wine bar. There they meet Clark, fresh from signing his divorce papers and sporting his favorite sweatpants, and his friend Will: charming, glib and avoiding his pregnant bride. Recognizing their similarities yet excited by the differences, the foursome climb into a party limo and navigate their way through embarrassing confessions, pot pharmacies, and covert skinny dipping; balancing an undercurrent of sexual tension and the sobering knowledge that they may have left their lives behind for this night, but they would have to return to them come morning.

Lauren and Katie, college frenemies with a mutual good friend, move in together at age 28 in order to afford an amazing Gramercy Park apartment. The unlikely pair start a phone sex line and become best friends while learning about this hilarious world of vibrators, fake orgasms and nighttime callers. When the hot line is hung up and reality comes calling, the most meaningful relationship of their lives is put to the test.