Dumped on his 27th birthday by his college sweetheart for being indecisive, Neil makes a silly bet that takes him on a wild ride through New York’s singles scene, accompanied by four testosterone-packed imbecile buddies and one crazy scheming New York taxi driver. On these madcap adventures Neil journeys from life choice paralysis to real life manhood.

After falling out with his editor, a fading political journalist is forced to interview America's most popular soap actress.