Greg serendipitously meets a young lady at a coffee shop who shares his taste in Sci-fi. Greg knows that this one is special, so he immediately sets his "Seal the Deal" timer. The fact that they get along so well should bode well for Greg, but will he really be able to seal the deal in 12 hours or less?

Tensions are high after numerous failures. Frustrated, Amelia goes wandering the streets in search of a ready and willing penis. What she finds may be more than she bargained for...

Greg and Amelia venture to Washington Square Park to cat-call NYU students. Amelia finds Beard, who invites her to attend a rally with him. Amelia hopes that this "date" will lead to a cozy and sexy bed, but does that even exist?

Greg gets some solid advice from Duke and goes home with the bartender. This girl likes to rage. Will Greg be able to keep up?

Amelia goes home with an intelligent and charming young bookstore clerk, but is he really what he seems?

Greg goes on a date with Joanie, who may or may not have some kind of contagious illness. Greg must tread lightly in order to avoid breaking any rules.

Greg and Amelia realize that they've only slept with each other, so they agree to open up the relationship in the months leading to the wedding. In effort to be safe and respectful, they set up six rules to abide by while on their escapades.