Alice Andrews is living in Manhattan, working as a reporter in Newark, and spending her free time desperately trying to forget her most recent relationship, with Miles, the smooth-talking investment banker she had mistakenly anointed Mr. Right. Then, on an airplane, she meets handsome Jack Russworm, a third-generation Harvard-educated doctor. With his perfect teeth and good luggage, he shows all the potential for being the real thing.

The new romance seems to be going well, but the issue of their different backgrounds keeps popping up. Clair, Jack's mother, seems frosty to Alice. Jack's ex-girlfriend, Sherry Steptoe, the poster girl for Black American Princess-dom, is a constant reminder of all that Alice is not. Amid the bougie clubbiness it is difficult for Alice to reveal who she really is, while Jack appears oblivious to it all. Or is he?