Young writer Sam has a crush on Birdie, the cute and quirky barista at his local coffee shop. When his conventional attempts to woo her crash and burn, he takes his efforts online, creating an Internet profile embellished with all of the details that would make him Birdie’s dream guy. When the harebrained scheme is a surprise success and Birdie falls for his exaggerated alter ego, Sam must keep up the act or lose his dream girl forever.
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
The film explores the history of the word throughout its inception to present day. Woven into the narrative are poetry, music, and commentary from celebrities about their personal experiences with the word and their viewpoints. Each perspective is unique, as is each experience... some are much more comfortable with the word than others.