Veteran comedy writer Charlie Berns, who is slowly but surely losing his grip on reality, befriends a talented young New York street singer Emma Payge. Together, they form an unlikely yet hilarious and touching friendship that kicks the generation gap aside and redefines the meaning of love and trust.

Alex Truelove is on a quest to lose his virginity, an event eagerly awaited by his patient girlfriend and cheered on with welcome advice by his rowdy friends. But Alex, a super gregarious dude, is oddly unmotivated. A magical house party throws Alex into the presence of Elliot, a hunky college guy, who pegs Alex as gay and flirts hard. Alex is taken aback but after a series of setbacks on the girlfriend front he takes the plunge and learns some interesting new facts about himself.

Living among fusty academics, an unusual young man gets between a high school history teacher and his wife.