Pretty in Black was the fifth episode of Season 5 of Roseanne, also the 102nd overall series episode. Written by Amy Sherman, the episode was directed by Andrew D. Weyman. It originally aired on ABC-TV on October 13, 1992.
The Conners enjoy torturing Darlene by making her think they're giving her a Sweet-Sixteen party for her birthday. The Conners meet their new neighbors, Ty Tilden and his daughters Charlotte and Molly.
It's Darlene's sixteenth birthday, and Roseanne wants to make it memorable. She plans a celebration behind Darlenes back. The Conners get some new neighbors, the Tildens: a single father who is raising two teen daughters on his own. Charlotte and Molly introduce themselves to the family.
Molly goes upstairs to say hello to Darlene, to Roseanne's amazement. "You have met Darlene, right?" she asks, as Molly walks away. Darlene is in the bathroom, dyeing her hair pitch black in an effort to make Roseanne mad, when Molly knocks. Darlene tells her to enter, and she hops on in, ready to chat. The conversation didn't go as well as Molly would've liked, but she told Darlene that she was sure they would end up being great friends. As she leaves, Darlene sarcastically says "Happy Birthday, Darlene!" to her own reflection- indicating that she is already fed up with her bouncy new neighbor.
Downstairs, Roseanne has gathered a birthday celebration, and calls her down. Darlene groans as she sees the living room is full of friends and family. They burst into a "sweet sixteen" song, and Roseanne places a tiara on Darlene's head. She compliments her new hair color. After snapping a few photos, Roseanne gives her the real present, a night out with her friends and David. Darlene is relieved, as she heads out with her group. Roseanne wishes her a Happy Birthday, and tells her that she hates her hair. Darlene smiles, and says, "Thank you mommy!" With the kids out on the town, the adults celebrate their own way. A game of "Truth or Dare" begins. Jackie and Roseanne spill some information about Crystal, that makes her very upset. Jackie and Nancy reveal that they are going into business together at the restaraunt Roseanne is not pleased, she feels left out.
At the end of the evening, Roseanne takes a final "Dare." Jackie dares her to run outside topless, and to go "flash Dan". Roseanne acts like it is no big deal, and heads to the back door. "Bra too", Jackie insists, and the bra comes flying off. Off she goes, topless, into the night. The ladies are laughing, as she runs as fast as she could, back to the house, covering herself with her hands. Dan walks in the kitchen, chuckling to himself, as he introduces Roseanne to the new neighbor, Mr. Tilden.
- Darlene wants a leather jacket, despite her feelings on animal cruelty and vegetarian lifestyle.
- On a dare, Roseanne takes off her shirt and bra and runs out to the garage to flash Dan. Upon returning to the house, viewers see a completely topless Roseanne from behind. Ann Marie quickly covers her in a blanket, and immediately shuffles her into the kitchen. When Roseanne sits down at the kitchen table, the blanket slips from her shoulder, revealing a bra strap.
- Darlene: I'm dying my hair black.
- Molly: Why?
- Darlene: Because I know my mom will hate it.
- Molly: You know what I do when I want to make my dad freak out? I put on my bright red lipstick.
- Darlene: (sarcastically) You rebel.
- Darlene: Is she planning a surprise birthday party for me?*Dan: Who?
- Darlene: My psycho freak of a mother.
- Molly: [to Darlene] Hi, I'm Molly Tilden. My family just moved in next door.
- Darlene: And, you're telling me this because?
- Molly: My dad said the owner gave you guys the keys.
- Darlene: Yeah, they're in the kitchen. Come in. Ah, I'm Darlene; this is David. Every house should have one.
- Roseanne: (sarcastically) So, did "Fisherman" dump you, yet?
- Jackie: No, but thanks for asking.
- Darlene: Okay, my birthday's on Friday, I'm turning sixteen, I'm getting my license, can I have a car?
- Roseanne: No.
- Darlene: Ah, it was worth a shot.
- Dan: Way to commit, Darlene.----
- Roseanne: Oh, and Darlene, I hate your hair.
- Darlene: Oh, thanks, Mommy!
- Ann Marie: (directing a question to Jackie in a game of "Truth or Dare") When was the last time you were felt-up at the movies?
- Jackie: It was last night! (gives an embarrassed laugh)
- Roseanne: You went to the movies by yourself last night!