Diary of a Bachelor is a comedy about Skip O'Hara (William Taylor), a well known playboy who is about to marry Joanne (Dagne Crane), a well to do woman. The groom finds himself in dire trouble when his soon to be wife finds his little black book. This diary contains a plethora of detailed accounts of his previous sexual exploits. Ever frightened, the poor Joanne reads on and the movie unfolds through a series of flashbacks. As the movie progresses, Skip's romantic life, both before and during the couples courting, is revisited in a comedic fashion. Not all is as it seems though, for as his conquests are played out it is revealed that his alluring lifestyle may not have been as fun as it appeared. Director Sandy Howard has created a lighthearted and hilarious view at how such a voracious sexual lifestyle might not be as fun as it might seem.