Caroline in the City S04E09 · Caroline and the Booby Trap

Overview

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.

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Episodes

1. 1 1. Caroline and the Guys in the Bathroom1998-09-21 · 22mActing as narrator, the Elevator Lady brings us up to speed on the events at last season's close culminating in Richard and Caroline's first kiss. Desperately aroused, Caroline and
2. 2 2. Caroline and the Office1998-09-28 · 22mWhen Carol can no longer stand the pressure Del is putting on her to work out of her new corporate office instead of her home, a reluctant Caroline discovers that Richard has been
3. 3 3. Caroline and the Rotten Plum1998-10-05 · 22mCaroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, An
4. 4 4. Caroline and the Drycleaner1998-10-12 · 22mIt's just not Annie's day: she gets fired from Cats after eight years and is immediately dumped by her agent. To get back some self esteem, she agrees to go out with her dry cleane
5. 5 5. Caroline and the First Date1998-10-26 · 22mOn Halloween, Caroline and Richard go on their first date, but she's disappointed when she thinks he didn't plan anything special; Del fears he's going to be fired. MacDermott: Edm
6. 6 6. Caroline and the Paper Chase1998-11-02 · 22mDel has hired Caroline and Annie to provide the voices for his new promotional video, but when he comes to pick them up it turns out they have to perform it for the boss first as a
7. 7 7. Caroline and the Big Night1998-11-09 · 22mCaroline and Richard's big night finally arrives, in the form of a romantic weekend booked in the perfect room at the perfect country bed and breakfast. What's wrong with this pict
8. 8 8. Caroline and the Diva1998-11-16 · 22mJealousy between Richard and Annie reaches a new height when Richard wants to attend an operatic recital to which Caroline invited Annie months ago. The two squabble so childishly
9. 9 9. Caroline and the Booby Trap1998-11-30 · 22mAfter 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 alrea
10. 10 10. Caroline and the Bar Mitzvah1998-12-14 · 22mRichard's Aunt Frieda announces that before she moves to Florida and wants to see Richard go through with the bar mitzvah he abandoned, and is willing to pay him $5,000 for the pri
11. 11 11. Caroline and the Fright Before Christmas1998-12-21 · 22mRichard, Del and Annie are apparently successful in their combined effort to knock the Christmas spirit out of Caroline, but when she appears to have lost all interest in her annua
12. 12 12. Caroline and the Big Bad Bed1999-01-11 · 22mCaroline becomes upset over what she sees as Richard's refusal to share his private life with her -- which comes to a head when Reg Preston's girlfriend kicks him out and he moves
13. 13 13. Caroline and the Horny Kid1999-01-18 · 22mDel and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer
14. 14 14. Caroline and the Firing Squad1999-01-25 · 22mCaroline is appalled to discover that Del (currently obsessed with buying a new Porsche) is paying his partner Charlie to stay at home so that his bizarre ideas won't compromise De
15. 15 15. Caroline and Joanie and the Stick1999-03-08 · 22mCaroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood chum, Joanie, whom Caroline once bullied in school. Mea
16. 16 16. Caroline and the Ancestral Home1999-03-15 · 22mCaroline and the gang visit her family's home in Wisconsin and learn her parents are selling the house. Distraught, she prolongs her stay (while Richard unwillingly bonds with the
17. 17 17. Caroline and the 2000th Strip1999-03-08 · 22mThere's to be a big celebrity banquet to celebrate Caroline's 2000th strip, but there's a snag: Caroline is completely blocked in terms of fresh, funny ideas. While everyone else w
18. 18 18. Caroline and the Sudsy Guy1999-03-22 · 22mCaroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to l
19. 19 19. Caroline and the Return of the Sudsy Guy1999-03-29 · 22mSparks fly between Caroline and Randy when he pays her a surprise visit in New York and they end up getting stuck together in a subway tunnel for two hours. Meanwhile, Richard gets
20. 20 20. Caroline and the Ultimatum1999-04-05 · 22mCaroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and wor
21. 21 21. Caroline and El Niño1999-04-26 · 22mAfter deciding they can't wait to get married, Caroline and Richard plan their nuptials for the following week. But while Caroline and Annie search for the perfect wedding dress, R
22. 22 22. Caroline and the Big Move1999-04-26 · 22mAs Caroline and Richard prepare to leave for Italy to visit his newborn son, Richard makes a confession that gives Caroline second thoughts about their future together: he never wa