Summary
Skip approaches "Bud" and begins to ask him what would happen if he asked his sister out. David recognizes this as the beginning of an episode he's familiar with, and tells Skip that he ought not to ask "Mary Sue" out right now. Skip is discouraged, but David tries to reassure him.
"I don't know what I'd do if she didn't go out with me," Skip says and shoots a basket, but doesn't make it in. The rest of the team looks over, shocked that he didn't make a basket.
In the hall, David tries to convince Jennifer to go out with Skip, saying that if they don't do what they're supposed to, they could "throw their whole universe out of whack." Jennifer tells him she's creeped out; she went to the library and found that none of the books had anything in them. Pulling out a tissue, she lights it on fire, but it does not burn, and she points out that they don't even need firemen there. Jennifer's friends giggle and come towards her, telling her that Skip is planning to ask her out and give her his pin.
At home, Jennifer dresses for her date with Skip, as David tells her to go along with it, before rushing off to work at the local soda shop.
David arrives at the soda shop, where he's greeted by Bill Johnson, his boss. Bill tells David that when he was late, he just kept wiping the counter without knowing what to do next. David looks down to see that Bill is just mechanically wiping the same spot over and over. David suggests to Bill that he can make the fries even when David hasn't put the napkins out yet.
That night, David works at the counter at the soda shop. When Jennifer and Skip come in, they sit at a booth and Skip thanks her for going out with him, calling her "the keenest girl in the whole school." David comes over and takes their order; Skip orders a cheeseburger and a cherry Coke, while Jennifer jokingly orders a salad and an Evian.
Skip tells Jennifer that he admired her report in town hall and is intimidated to talk to her. He tells her he wants to take things slow, and isn't even quite sure he's ready to hold hands, which visibly disappoints Jennifer.
Jennifer goes to the bathroom and goes into a stall, where she finds there is no toilet. Her three friends rush into the bathroom and ask her, "Did he give it to you?" to which Jennifer replies, "I don't think he knows how." The girls gush about the fact that Skip is going to take her to Lover's Lane and hold her hand.
Jennifer goes back to the table and tells Skip she wants to go to Lover's Lane. He looks intimidated as she drags Skip out to the car. Seeing them leave, David gets upset and chases them out of the diner, but they are already driving away. "You can't do this to someone who doesn't exist!" David yells after the car.
At Lover's Lane, Jennifer comes onto the innocent Skip, who tells her, "I didn't think you'd wanna come her until we'd been pinned for a little while." She replies, "Oh Skip, you can pin me anytime you want to."
Meanwhile, David hurries home, where he runs into George on the front porch. He tells George he's worried about "Mary Sue," and George tells him, "Bud, your sister's getting older now, and she'll naturally be going out with boys, but she's a fine young woman. She would never do anything for us to be concerned about."
The scene shifts to Jennifer moaning in pleasure in the car with Skip. Skip sits up abruptly and tells her that he thinks he is ill, motioning down to his erect penis, but Jennifer assures him, "That's supposed to happen."
At home, David eats cookies and drinks milk with his parents. There's a knock on the door and David runs to answer it. It's Bill from the ice cream shop who wants to tell David that he closed up the shop all by himself, even though he's never done that before. As he talks about his uncharacteristically spontaneous evening, Betty walks up and greets him. Bill and Betty clearly have an attraction to one another, and they stare at one another in silence.
Back at Lover's Lane, Jennifer thanks Skip for a wonderful evening, and Skip seems to be in a state of post-orgasmic bliss. "What did you do to him?" David asks Jennifer as she comes into the house, but she assures him that it was a nice time and goes up to bed.
As Skip drives through the neighborhood, he looks over at a patch of roses, one of which has turned red. He is shocked by the sight of color in his black-and-white world.
The next day, David looks for the repairman in the television in the living room. The weather channel reports that once again, the weather will be 72 degrees all day without a cloud.
At basketball practice, David sees Skip telling the boys on the basketball team about his night with Jennifer. As they go to shoot baskets, everyone on the team misses. David goes to Jennifer and tells her that she's messing with the entire universe. One of Jennifer's friends calls to her by a new nickname that Jennifer has evidently taught her.
"But they're happy like this!" David insists, to which Jennifer replies, "No one is happy in a poodle skirt and a sweater set." Jennifer tells David that the people in Pleasantville don't want to be geeks and have a lot of potential, before alerting him to a girl nearby blowing bubble gum that is a bright shade of pink.
At Lover's Lane, couples begin to do more than just hold hands. The basketball team gets worse at basketball. The furniture store begins selling a double bed for couples. A girl's tongue turns pink. All the while, David searches the television for the repairman, in hopes that they will be able to return to their real lives.
One night at the ice cream shop, David goes in to find that the teenagers inside are much more liberated than before, openly kissing and listening to rock and roll. Jennifer asks David for two cheeseburgers and two cherry Cokes, and he puts the order in.
"There are no cheeseburgers," Bill says, sitting on the ground behind the counter, dejected and clearly having an existential crisis. David takes him to the back to have a talk, where Bill complains about the monotony of flipping burgers. "Look, you can't always like what you do. Sometimes you just gotta do it because it's your job," David says, trying to motivate his boss.
Bill tells David that his favorite time of year is Christmas, because every year he gets to paint a mural of a different thing. He pulls out a book of photos and shows David all the different murals he has painted. "Wow, that's pretty good," David says, looking at the murals, but then advises Bill not to think too much about the fact that he doesn't like his job.
At the barbershop, George and some other men discuss the fact that the basketball team has been losing. Suddenly, the mayor, Big Bob, comes in and takes the spot of the man getting a haircut, saying that the basketball team has never lost.
At the Parker residence, Betty and some friends sit around the kitchen table playing cards. One of the women talks about her daughter whose tongue turned pink and tells the women that the color has spread to her daughter's lips. Another woman says that she saw a green car in front of the ice cream shop, as the camera zooms in on Betty's face, listening. When she picks up her cards, Betty is shocked to see that they are now colorful.
Later, while doing the dishes, Betty asks Jennifer what happens up at Lover's Lane. Jennifer tells her mother that kids are having sex and Betty asks, "What's sex?" Jennifer explains sex to her mother.
Betty is shocked to hear about sex, telling Jennifer, "Your father would never do anything like that." Smirking, Jennifer tells Betty that she can enjoy herself without George.
Betty draws a bath as George gets ready for bed. She removes her clothes and gets in the bath, before masturbating. As she does, items in the bathroom become colorful and the tree outside lights on fire.
Analysis
In this section we begin to see that not only are David and Jennifer trapped inside Pleasantville the place, but they are also trapped inside the show itself. When Skip asks David if he can ask Jennifer out, David realizes that he is actually inside one of the specific episodes. Not only is the setting identical to that of the show, but Jennifer and David must navigate the designated script as well.
The script is a powerful component of Pleasantville, to such an extent that when David tries to diverge from the events as they are meant to unfold, it has immediate consequences. When he tells Skip that he shouldn't ask Jennifer out on a date, Skip emotionally short circuits almost instantly. His permanent smile is replaced by a defeated stare, as he says, "I don't know what I'd do if she didn't go out with me." Then, when he tries to score a basket, it bounces out of the net, something unheard of on the Pleasantville basketball team.
The fact that the citizens of Pleasantville are so intent on sticking to the script makes David and Jennifer responsible for the well-being of the community. It's not only that Skip's continued success is contingent on Jennifer agreeing to go out with him; when David arrives late to the ice cream shop, he finds that his boss, Bill, is unable to figure out how to do his job without the routines that he is used to fulfilling with David. Thus, the success of the ice cream shop is contingent on David playing his role effectively. Not only must David and Jennifer find ways to get back to their real lives, but along the way they must conform to strict and immovable guidelines.
A great deal of the film's comedy comes from the contrast between the innocence of Pleasantville and the worldliness and irreverence of Jennifer. A teenager who is used to riding in the fast lane, Jennifer is regularly exasperated by the limited scope of Pleasantville teenager life and determined to have fun and break the rules as much as she can. When Skip asks her on a date, he is the epitome of a gentleman, but Jennifer is impatient with his lack of physical experience and decides to take the upper hand sexually with him, regularly making innuendo and rolling her eyes at his "aw shucks" attitude.
As Jennifer and David begin to relax the attitudes of the Pleasantville citizens, it has an effect on the actual environment of the town. After David teaches Bill that he can autonomously affect his own business, and after Jennifer has sex with Skip, the world slowly begins to fill with colors. Skip sees a red rose in the night, bubble gum becomes pink, and car lights turn red. As the citizens are awakened to the colorful turns their lives might take, the world literally begins to fill with color. The 1950s conservativism of Pleasantville is gradually unwound by the looser sexual morals of Jennifer in all her modern empowerment.
