Based on the best-selling book by Greg Behrendt and Liz Tuccillo.

The Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior. Jennifer Connelly plays a woman stuck in a tired marriage with Cooper's character. Kevin Connolly, meanwhile, is a man pining after a woman, still not cast, who is having an affair with Cooper.

Goodwin is a young woman obsessed with Kevin Connolly's character who tries to set up accidental meetings with him only to run across his friend, played by Long, who takes her on as a "My Fair Lady" experiment.

Barrymore plays a woman perpetually confused by dating, now more than ever in a culture that is more obsessed with technology than actual human contact.