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.

Will Karen and Doug's cheatin' hearts tell on them, or will Leo? Meanwhile, Isabel ain't misbehavin' but feels guilty anyway when she runs into Everett while jogging; and Jennifer receives an ominous letter from one of her professors.