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.

As Valentine's Day approaches, Leo is strung out with work, and Isabel goes out to a concert with Everett. Meanwhile, Alan notices that his wife is "glowing."