Leo and Isabel throw a New Year's Eve bash, but the guest list doesn't preclude party crashers from showing up---including Everett, Isabel's ex-fiancé.

During an intimate moment, Leo tells Isabel he wants to marry her, but both are confused about the statement's meaning. Meanwhile, Karen slyly arranges to visit Doug.

Jake refuses to explain why he's desperate for $100 in cash, but sees an opportunity to earn it by chauffeuring Isabel's visiting cousin, Anne. While driving Miss Annie, though, Jake begins falling for the quiet, contemplative girl.