Premise: Henry Beckman was a big fish in the small pond of Amsterdam, Mo. But then he let his girlfriend Heather talk him into moving to Chicago to work for her family business -- and that's where it all went wrong. In one morning, Henry's dumped by Heather, learns he doesn't have a job anymore and gets kicked out of their apartment. Henry then moves in with flashy Larry Cone, a modern-day Dean Martin who decides to take Henry under his wing -- teaching him the wisdom of staying single and living the good life. Under Larry's tutelage, Henry begins to rebuild his life and starts working for Larry's childhood friend Amanda, a gal who's unsuccessfully trying to emulate her perfect ideal of womanhood: Kelly Ripa.