“I think we all know what's going on here. Up until now everything around here has been, well, pleasant. Recently certain things have become unpleasant. It seems to me that the first thing we have to do is to separate out the things that are pleasant from the things that are unpleasant.”
The mayor addresses the black-and-white citizens of Pleasantville and talks about the fact that things have been changing in town, and that it threatens the business-as-usual lifestyle to which many of them are accustomed. This marks the first backlash against the liberation that is taking place in town.
“Well maybe it needs to be messed with, David. Did that ever occur to you?”
Jennifer is responding to her brother’s concern that her behavior and actions are having consequences within the world of Pleasantville that the residents are not prepared for. Her response reveals her 1990s sensibilities and the fact that she thinks people deserve to be shaken out of the status quo.
“Well, you know, Mom, there are other ways to enjoy yourself...without Dad.”
Jennifer talks to her Pleasantville mother, Betty about the ways that she can fulfill herself without the help of her husband George. In a humorous reversal, a daughter teaches her mother about sexuality, and in particular, masturbation.
“There is no right house. There is no right car.”
David says this at the end of the film to his real-life mother as she weeps in the kitchen about the fact that her life hasn't turned out the way she expected. Changed by his time in Pleasantville, David accesses some inner wisdom to remind his mother that there is no one way that life is supposed to go, and that it's important to embrace its uncertainties.
"Where am I going to see colors like that? Must be awfully lucky to see colors like that. I bet they don't even know how lucky they are."
After David gives him the book about art history, Bill is excited about the prospect of expressing himself through painting. Soon, however, he is discouraged by the fact that he will never be a great painter because his life is in black-and-white.
"Look, you can't always like what you do. Sometimes you just do it because it's your job. And even if you don't like it, you just gotta do it anyway."
After David teaches Bill that he doesn't always have to do things the way he's always done them, Bill feels liberated, but also begins to resent his work more and more. He bemoans the fact that he doesn't like making hamburgers over and over again, and David teaches him another lesson, that sometimes work is hard, but it's important to keep going.
"Nobody's happy in a poodle skirt and a sweater set."
David tries in vain to advise Jennifer not to mess too much with life in Pleasantville, insisting that the citizens are happy, but she has other ideas. In a comedic moment, Jennifer suggests that no one is happy "in a poodle skirt and sweater set," suggesting that even if the citizens of Pleasantville think they're happy, they don't know what's good for them.
"I did the slut thing, David. It got kind of old."
At the end of the film, rather than returning to their old life, Jennifer opts to stay in Pleasantville. There, she has discovered the joy of reading and learning, and is convinced that she has a brighter educational future in Pleasantville than back in the 1990s, where she was a popular girl in the fast crowd. Here, she tells her brother that her promiscuous days are behind her, and she wants to pursue a new way of life.
"...maybe it's not just the cooking or the cleaning you miss. Maybe it's something else. Maybe you can't even describe it."
In court, David tries to make a point about the fact that turning colors is not necessarily a bad thing. He goes to his Pleasantville father, George, and questions him about the fact that he misses Betty. He tries to dig beneath the surface of George's feeling, the fact that he misses having a wife, to try to get George to think about the ways he misses Betty as an individual.
"What's sex?"
This is a humorous line, addressed to Jennifer, in which Betty reveals she has no idea what sex is. Even though the adults in Pleasantville have children, they live in a completely sexless society. Thus, it is up to the worldly Jennifer to school her mother on the birds and the bees.
