Christian Black introduces shy college student Hannah Steale to the world of "romance" after she interviews him for her school newspaper. Their kinky relationship stumbles forward despite Christian's shortcomings as a lover and the antics of his racist adoptive mother Claire, his well-endowed brother Eli and Hannah's hyper-sexual roommate Kateesha..

Chronicles the 1989 summer afternoon when the future President of the United States, Barack Obama, wooed his future First Lady, Michelle Obama, on a first date across Chicago's South Side.