Caroline in the City

Caroline and the Booby Trap (4x9)

Air date: Nov 30, 1998

After Annie is beaten out in an audition by an untalented but well endowed rival, she announces her intention to have breast augmentation surgery during a Thanksgiving dinner already complicated by Del's turning up with a frozen rather than pre-cooked turkey and the bizarre behavior of mailroom Dave. Unable to talk Annie out of it, Caroline then beats her to the doctor's office to consider treatment herself after Richard's ill-timed admission that he has fantasized about her with larger breasts. A fantasy sequence in which Caroline imagines special treatment aboard a plane convinces her to stay with what she's got. Meanwhile, Richard has taken Caroline's riposte (that she has imagined him with darker, sexier hair) to heart, but when Del's current girlfriend shows up to rescue him from the effects of an amateurish home dye job, she realizes Del stood her up for Thanksgiving and storms out, leaving Richard to deal with a bad case of chemically induced hair loss.