Hidden in the midst of straight-to-video releases, this film is a head and shoulders above the rest, and it boggles my mind that it did not achieve theatrical release.
While the subject matter is somewhat unoriginal (Games a man must play to land a "perfect woman" and the pros & cons of commitment/marriage), the film has a magnificent script that gives these themes a freshness not seen since Swingers.
Perhaps the film's strongest suit is the cast. Reynolds, Bellamy, O'Connell, and Livingston work great together, and never once does the witty dialog seem forced or unbelievable. The interaction seems realistic, and most importantly, personal (from the male standpoint, anyway). The film is smart and thoughtful, giving a variety of perspectives on the subject matter.
The only beef I have with this film (no pun intended) is that the ending is a bit abrupt (I won't give anything away, but you'll see what I mean). I felt a little more elaboration might have tied things up a bit better. However, don't let this deter you, Buying the Cow is a must-see.