Chauncey "Cool" Brown has just been named one of Soul Sista magazine's 25 Most Eligible Bachelors and the news couldn't have come at a better time. His business, C&J's Rare Grooves, is struggling to stay afloat, but Soul Sista has a suggestion that could change everything: write a column for their website where he documents his dates with three women selected by their readers.

Cool signs on, mainly for the publicity that he believes it will generate for his business, but he quickly learns that he might have bitten off more than he can chew. Now, in addition to trying to save his business, he finds himself facing an even more daunting challenge: opening himself up to the possibility of falling in love.