Headscratchers / Pleasantville

How will David explain his sister leaving the real world?

Just how the hell will David explain to his real parents that they'll never see Jennifer ever again?

• He may not have to. Note the ending — the whole events of David's time in the show take up just one hour of real time. So Jennifer could conceivably spend three years in college and then return with about a weekend passing in the real world. Now given Jennifer being who she is, would it really be so surprising for her to just vanish for a random weekend? Doubtful - especially with her brother covering for her.
• That explanation above is indeed Word Of God according to Gary Ross' DVD commentary (although he admitted he made up that explanation on the spot). 1 hour in real life = 1 week in Pleasantville. Three years of college works out to be about 6 days.
• Made up on the spot or not, it makes perfect sense. Most shows are 1 hour long and run once a week.
  • This is actually backed up by the movie itself. When David transports back to his world the TV announcers says that the first hour of the "Pleasantville" marathon has passed. David obviously spent several days in the TV world.
  • It's more than "several days". They arrive in April 1958 (we see the calendar in the first scene inside the show), and Jennifer is leaving for college when David comes back. Since she would have to finish high school first, it's at least June and more likely August at the end. If four months = one hour in our world, four years of college is twelve hours. So at worst, Jennifer would only be gone for that one night. I rather suspect her mother is used to that! (Yes, this contradicts Gary Ross' timeline of 1 hour = 1 week; but even Ross himself said that wasn't based on anything.)
• He'd still have to explain how she aged. Even a couple of years does wonders when you're gone. Party hardy, maybe.
• Maybe Pleasantville runs on Comic Book Time and she won't age...
• Or maybe she'll just age in people years and won't show dramatic aging after a year or two. But hey, I could be wrong.
  • Three years isn't actually that much when you're Jennifer's age - even if she ages, it won't show THAT much. She could put it down to maybe getting a full makeover while out of town for about a week. It's not like she'll have lost three years of her life; just... misplaced them. And if she doesn't age, problem solved.
• What about the thing they did in The Chronicles of Narnia? Those kids were there like fifteen years living there and aged normally, but when they got back into their world, they were children again.
• This is sort of supported. When David is about to be transported back to the real world, he has his hair combed back and is wearing a basketball jacket. When he's back in the real world, he looks the same he did when he first left, although he still has the jacket.
• I figured that, when David came back but Jennifer didn't, the same reality warping magic that was transforming Pleasantville altered the real world so that there never was a Jennifer.
• There's almost certainly some Narnia stuff going on; no matter how long the characters spend in the TV world, they will no doubt return to their own world looking no different than when they left and within a time span that won't cause anyone to wonder to much where they've been.
• It doesn't matter: both of their parents are totally wrapped up in their own lives. Jennifer & David were already going to spend the weekend completely alone anyways. The explanation of "Jennifer taking off somewhere for a few days" would only be needed if worst comes to worst: that the parents will realise that they haven't seen her recently & actually start asking questions.

Is Pleasantville worse off now?

• Maybe people in the actual 1950's weren't happy, but these were actual fantasy characters designed to be happy. Happiness is relative anyway. If you have 10 dollars, you want 20; if you have 20 dollars, you want 40. These people actually had everything they wanted because they honestly didn't know any better (unlike in the real 50's, where they pretended not to know or had feelings glazed over). But Witherspoon's character had to screw it all up, and the movie makes it clear she did it for her own amusement. Now they're saddled with the desires we have. You know, the ones we drive ourselves miserable chasing after, the ones that will never be satisfied. If these people had wanted these things for themselves, they would have snapped themselves out of this mode the way we did. They wouldn't have needed an outsider to do it for them. This makes the whole exercise of this movie either: a) tragic, b) pointless, or c) a worthless Strawman argument.
  • You're missing the point. The Pleasantvillers (is that a word?) only know complete averageness of feelings. They can't suffer because they don't know sadness, but they don't know happiness either; they have no desire for advancement, but their existence has no point; they don't have the aching need to fulfill their desires, but they don't have the satisfaction of doing so; they don't get sexually frustrated, but they don't get orgasms. Which life would you prefer: one in which your feelings are always stuck exactly in the middle, or one that allows for suffering, but also allows for happiness?
  • Someone obviously hasn't read 1984.
  • It's the inverse of Invasion of the Body Snatchers, with emotions being introduced to the citizens, seen from the POV of the "invaders".
  • You're 100% right, original guy, but it's still not a sell you can make. Because everybody in our world with our messed up human emotions IS happier once they rationalize the terrible things they're stuck with as being in some wholly unsupported way 'for the best'. So we say 'loss makes you appreciate what you have more', and 'failure teaches you more than success', and 'change destroying everything you care about is fine because it brings with it exciting new things'. Because we'd rather live in OUR fantasy world where those things we have absolutely no power to get rid of are in some way to our genuine benefit... no, even BETTER than what everybody else has. Just because they're ours and we can't not have them. So we ruin everything of theirs until whats ours is all they have to cling to and portray it as a victory to convince ourselves, again, for the eightieth time, because for SOME reason it keeps not sticking.
  • Yikes. Leaving aside that an entire universe was essentially lobotomized (in the original 1950's idea of what the procedure was supposed to do for you) and frozen in time, and of course freeing the people from this condition was worth a brief struggle by most systems of morality... Think of it as a refutation of Plato's Allegory of the Cave. Two outsiders came in and told all the people they'd only been looking at shadows, and living in chains all this time. There was some strife, but one by one the people accepted their freedom and wandered out of the cave. Eventually the whole town was saved. Score one for human intelligence and resiliency! Everyone chose the real world and all its pains and complexities. If you wouldn't, that's dystopian fanfic territory.
  • That is one alternate interpretation of the tale, and a valid one. But the story is primarily focused on anti-nostalgia and anti-escapism, so there's not really much room to discuss the negative aspects of the changes Pleasantville has gone through.
  • This isn't really a headscratcher as much as it's the whole philosophical argument the movie is engaging in. To quote Carl Jung: “Even a happy life cannot be without a measure of darkness, and the word happy would lose its meaning if it were not balanced by sadness.” The argument goes that in order to fully understand happiness, and thus be truly happy, you need to have at least some understanding of what it is to be unhappy in order to contrast it; essentially, you savour happiness because you also know what it is to feel the lows of sadness, loneliness, discontent etc. Otherwise, what you understand to be 'happy' would be artificial and meaningless. The inhabitants of Pleasantville are 'happy' in the sense that they don't really experience anything bad, but the whole argument of the movie is that they're not really alive or fully human either, because their concept of 'happiness' has nothing to contrast against and thus give it meaning. To illustrate; the basketball team always wins the game because winning is 'good', but it doesn't really mean anything or give them real satisfaction because they've never experienced what it means to lose the basketball game, and thus don't have the drive of avoiding that feeling to make the victory sweeter. The 'happy' marriage goes through the motions of domestic bliss, but it means nothing because they've not had to work to reach a true intimacy, which requires hard work and potential disappointment. Everything is hollow because the victories don't really mean anything, and everyone's just artificially going through the motions of everything being nice and, well, pleasant. The movie is making the case that while it might not always be 'better' in an 'avoiding pain and unhappiness' sense, introducing colour — and thus moral complexity and the possibility of hurt and pain, among other things — into the lives of the people of Pleasantville is unarguably better in the sense that it makes their lives real, and thus gives them the possibility of finding true happiness and meaning rather than just going through the motions of faking it. It's entirely possible to disagree with this argument, of course — but that doesn't make it a plot hole nor is it the filmmaker's problem if you do.
  • Also the movie doesn't seem to support the idea that the people of Pleasentville are actually happy. Note that Bill talks about how much he looks forward to painting the Christmas display for his store every year before he's had any concept of color. And when his eyes and Betty's meet there's a deep lingering longing look like there's an attraction there well before Betty even has the bath scene. They don't have the words to articulate it but it's really implied they're not actually happy, at best the feel a surface level "pleasentness" but there's a pain lingering a lot down for a lot of them them because they feel unfulfilled.

The outside team playing in Pleasantville

• If there is no "outside of Pleasantville", then who is the basketball team playing against? And if the Pleasantville team always wins, then that means someone always loses. It surely isn't pleasant for them, whoever they are.
  • It seems obvious that Pleasantville's general idealism means that nobody was expected to really think about it. Alternatively: "It's not the winning, it's the taking part that counts."
  • According to the DVD commentary by director Gary Ross, he explains that the opposing team is indeed an unknown visiting team that is perpetually always in town playing against Pleasantville, a la the Washington Generals in relation to the Harlem Globetrotters.
  • Wow, now that is a Fridge Logic Fate Worse than Death. You're stuck outside of your (non-existent) home, always losing The Big Game , forever. Even if they're too lobotomized by the Fisher Kingdom powers of the setting to notice, you can't help but sympathize.
    • Since one theme of the film is that 50s utopias were never well thought-out, one could argue that the visiting team members were the least developed characters of all and probably barely existed in terms of self-awareness. They probably weren't existing outside of the portions of episodes when a basketball game was being played.
  • Being that they don't know rivalry, they are probably driven entirely by the desire to just do sports, without caring for whether they win or lose. Notice that when Pleasantville loses, but real feelings haven't yet exploded in town, the players don't seem too concerned about their loss either.
  • I'd have guessed cross-town rivals, myself.
    • It's not out of the realm of possibility that a town has more than one high school. Like Beverly Hills High vs. West Beverly for example. And makes sense in the scheme of no "outside of pleasantville."
  • Storybrooke, Maine.
  • Well a lot of things don't make sense with a limited geometry. Where are they getting their water? Food? Supplies? At some point they will cease to able to produce what they have in such a limited space. Where are they getting the supplies they don't use? Someone has to make them. Who brought in all those books for library? How about the United States? Do they or do they know how it's history if they have it's flag?
  • I always assumed that everything kind of poofed into existence when it was needed. Grocery store low on food? A food delivery poofed into existence coming around the corner driven by the same truck drive thats been delivering there for years. As for the rival basketball team, I kind of figured they worked the same way. When it was time for the big game, there bus poofed into existence coming up the street and parking at the school gym. Then once they lose, they all loaded up and drove away, and once they were out of sight, poofed away till the were needed again.
• Where do Buddy Holly and the other banned musicians come from? Are they Pleasantville natives? Is Holly dead or is death by plane crash too unpleasant? And why would he or anyone be on a plane anyway? Presumably planes just sort of exist, like firehoses.
  • I figured the real-world music came in the same way the text appeared in the books, once someone familiar with it was there to bring it to the others' attention. Also, the movie takes place in the spring of 1958, when Buddy Holly was still alive in the real world.

What happened to the original Bud and Mary Sue?

• What happened to Bud and Mary Sue? I understand they were replaced when David and Jennifer came, but when David left, did the real Bud come back?
  • Additionally, if he did come back, how would he adjust to the radical changes that took place while he was gone?
  • I always figured that Bud and Mary Sue just took the places of the main characters in the real world. Considering that they pretty much had to have gotten used to differences in people and changes in society while they were in the "real world", they shouldn't have too many problems returning back to Pleasantville. Hell, the still changing, fairly conservative Pleasantville would probably be a relief from David and Jennifer's world. Or, alternately, they went completely insane from the culture shock and won't notice the difference anyway.
  • Remember the whole timing issue - even if Bud has lived in place of David, it's only been an hour. A ridiculously confusing hour, no doubt, but just an hour nonetheless - he wouldn't have had time to adapt to the real world. It might, however, have shocked him enough that modified-Pleasantville, which is now somewhere between old-Pleasantville and real life, would still look like a lot better. Alternatively if he hasn't lived in David's time he just comes back, gets the culture shock of his life, and then adapts like everyone else in Pleasantville has already done.
  • I assumed Bud and Mary Sue cease to exist. They were never real so it doesn't matter. The real “Bud” is David and the real “Mary Sue” is Jennifer. Both of whom take a town full of fictional characters and help transform them into real people.
  • The "Pleasantville" that the movie is set in is most likely some kind of parallel dimension based on the TV show created by the remote control rather than the actual, literal TV show. If so, then there probably wasn't a "Bud" or "Mary Sue" before David and Jennifer showed up, because the dimension was made "for" them, fully formed, with everything set up for them to occupy those particular roles.
  • David and Jennifer probably merged with them or vice versa, and it’s very likely that they’re gone forever.

Will toilets appear in Pleasantville?

• Will the toilets appear in the soda shop now?
  • You probably meant that as a joke, but I can't resist answering the question. Yes, if the map outside of Pleasantville fills in, that would suggest the emergence of other common infrastructure.
  • Unless the toilets were smashed when the shop was ransacked.
    • What a perfect time to install new ones!
  • A better (if squickier) question might be, if the toilets have all appeared, but the residents of Pleasantville haven't ever used a toilet before, does that mean we now have an entire town full of people who need to be individually toilet trained?
    • Think of all the unused food sitting in them up until this point. That food has to come out on their first BM... and they're not trained!
    • There's no reason to think that every single bit of food they've ever eaten is just sitting around inside them. The food just goes into them and disappears without thinking further about it, like every other inconvenient or "dirty" thing.
  • Wanna get into icky problems related to their newfound biological needs? Forget toilets - let's talk pregnancies. No systems for birth control, and they've all just discovered sex and are collectively doing it like rabbits. You do the maths.
    • Didn't something similar actually happen in the real world around the same time period?
    • Not exactly like the movie shows, of course, but yes, it did. Believe it or not, the teen pregnancy rate was actually higher in the 1950s than in any decade since. There are several reasons for this, not all of them "bad" reasons as such (for example, the average age of first marriage was much lower then, so some of those pregnant teenagers were 18- or 19-year-old women who were already married and wanted to get pregnant anyway), but it was also partly because no one was teaching teenagers about how babies are made and how to avoid it. Even if teenagers knew about contraceptives, they were illegal in many places anyway.

What good is a Pleasantville college degree to Jennifer?

• What good is it for Jennifer to go to college in the Pleasantville universe? It's not like it'll change her (presumably shitty) real-world grades, nor will her Pleasantville degree be honored by real-world employers. Does she plan on staying in Pleasantville forever?
  • She could just be going to college because she wants to learn. Her big color changing moment is when she chooses to stay home with a book rather than go out with Skip, because reading is fun and learning is its own reward.
  • Besides, as discussed above, with Year Inside, Hour Outside, in several days of real-life time she would return with all the knowledge of a post-graduate. Then she'd just take an external degree in the real-life analogue of the institution she'd gone to in Pleasantville.
    • Wouldn't she get lonely and become maladjusted for that long with her college mates being semi-fictional people who have been awakened to life in artificial ways? Also, where is a college?
    • Except her knowledge would be a half-century out of date.
    • Well only some of it, she'd miss out on recent developments and all her history would be out of wack from the 50's inaccuracies, but most of her math and science would be the same, English too.
    • We have entire tropes like Science Marches On dedicated to why a world set in the 1950s would give Jennifer a nearly worthless science education in the world of the late 1990's/early 2000's.
    • Who says she's going to be focussing only on science? In any case, she'll almost certainly return to her own world no older than she left it, just like her brother did, so she'll have plenty of opportunity to correct any gaps or errors in her 1950s education.
  • She'll have learned how to buckle down and study, and she'll have matured, making mistakes and learning from them. Those mistakes won't affect her real life and she'll still be the wiser for them. And yes, she'll have learned a lot - psychology, medicine, geography, math and numerous science majors still have a lot of information that is used today. Not to mention her history is only missing 50 years - American history has been around for a lot longer than 50 years and hasn't changed a lot in how it's taught. Alternatively if she decides to throw it all away and party constantly, she'll have it out of her system by the time she gets back.
    • One hopes that even if her Pleasantville degree won't do her much good in the real world, it can at least prepare her for earning a real degree there.
  • I don't see the problem. She'll be away six days; when she gets back, she'll have plenty of time to fill up the fifty years of history she's missing, and she'll have a lot of background on which to build this knowledge.
  • Yeah, that was the only part of the movie that really grated with me… I did kind of wonder how her twin brother explained that one to the rest of the family. Also, you’d think that people would raise eyebrows when she showed up with her “Class of ‘58″ high school diploma or whatever. And what if the show got canceled by the network? Would that leave her in limbo or something?
  • There's almost certainly some kind of Narnia Time thing going on with Pleasantville. David/Bud spends a week or so in Pleasantville, but when he returns home it's probably only been a couple of hours at most. For all we know, Jennifer showed up again maybe a few more hours later, looking no different but having undergone something of a personality shift.
  • Even if it's too late for her to get into a good college in the real world, there's always community college for a year or two, and with her newfound work-ethic and the knowledge she picked up in college in the '50s, she'd have no problem making better grades to transfer to a better school. (The bigger problem might be convincing her mother to pay for it.)

Parents don't notice their kids are replaced

• Did Betty and her husband realize that Bud and Mary Sue had been replaced/weren't their actual children? Surely the radical personality changes would have been a clue off.
  • At first, no, because remember no one in Pleasantville feels anything really unpleasant. If they noticed Bud and Mary Sue were acting differently, they would have chocked it up to some utterly mundane and vanilla childhood problem (like not having the newest pencil that all the other kids are using). It would have been like a world-class case of denial where any personality alterations would have been instantly rationalized away and forgotten about. Clearly by the point where the whole "anti-colored" movement had started they know something is up, but they're too busy reeling from all the other changes going on to really put everything together. By the end, David and his sister have clearly explained it to them, considering that Betty is saying goodbye to David at the TV.
  • The best guess is that it works similarly to Sam Beckett in Quantum Leap. They are different people, but everyone else sees and hears the original people. Just like in Quantum Leap, nobody would make the assumption, "Gee, they sure are acting different. I bet they've been replaced by somebody else temporarily." Because that's pretty far fetched. The only difference is that there is no goal of "leaping", hence no point of keeping their identity a secret and thus you have the ending where the Pleasantville folks understand that Bud and Mary Jane aren't the same people.

Introducing colors and sex to Pleasantville

• How do they know what colors are if everything is monochrome? Also, how do they not know of sex if they had children?
  • Taking into account that Pleasantville is a show, you could think that it poofed into existence with all of them in their pre-defined positions, and not knowing anything else than they need to make their sitcom.
    • That's how I interpreted it. You'll notice that the first few times Dave and Jennifer break the routine, the others just sort of glitch and repeat their cues, kind of like a videogame AI.
  • When things start colorizing, a background character mentions seeing something that was "red red." I got the impression that while characters are aware that everything's in black & white, the concept that it was black & white versions of colors was kept in place.
    • This is also seen at the town meeting once the issue starts getting more urgent. One woman accuses a man's door of being "blue". His response is "it's always been blue!" so they've always known the color things were, but now they can actually see it.
  • Pleasantville parodies older TV shows, and one aspect of this parody is that they never address things like sex, or even allude to it. Shoot, in the 1950's, married couples on TV couldn't even share a bed.
  • The way I see it their wants, desires and feelings were never completely absent, just sorta turned into standby mode. They always had very vague notions of them: they knew what colors were, once the use of their genitals was explained to them they didn't need any more encouragement, and Johnson already took a very diluted form of pleasure in painting the bar's window. David and Jennifer coming in town didn't create anything that wasn't already there - they just upset the equilibrium and got the Pleasantvillers out of their standby mode.

Fire never seen in Pleasantville

• So, why were there no fires in Pleasantville before David and Jennifer showed up? Surely they enjoyed restful evenings next to the fireplace back then.
  • Yes, but they never got out of the fireplace. Nothing "bad" happens in Pleasantville. That's sort of the whole premise of the setting.
    • I was just about to add that I remembered that they had fire pretty much under control. After all, their food was cooked.
    • Yup, they just didn't have any concept of a "fire fire", much like they were shocked by something being "red red".
  • No, there were no fires at all. Jennifer explicitly states that nothing burns, and takes out a handkerchief and a lighter to prove so. People also stared at the tree on fire without any concept of what it even was.
    • The lighter's fuel burned, didn't it? It was small, but it was indeed fire. Fire that was meant to exist. If I recall right, Jennifer noticed because she couldn't light a cigarette. Presumably because she was a teenage girl and not meant to smoke in that universe. A grown man probably could light a cigarette or cigar. Similarly, the tree was not ever meant to burn, so it was impossible until that moment, hence the surprise.
  • Or the soda shop's grill.

Gaining color though sex?

• Wow the mom is in color now! Great huh? Until you realize gaining color is usually associated with sex, her husband was still black and white
  • Gaining colour was associated with Character Development. The husband gained color when he felt real love for the first time. With regards to sex, the mom said her husband "would never do that kind of thing" for her, meaning he is oblivious of sex as much as she was. Hence the bathtub scene and the tree bursting into flames.
  • The above is correct. Though it's quite clear what she's doing in the bathtub but not everybody who had sex was in color and not everybody who was in color ended that way because of sex. Bud's change occur when Bud he defends his TV mom from the bullies and Mary-Sue's when she decides to study instead of having sex.
    • Ultimately it's not about the sex, but what the sex represented for many of the people. For Mary-Sue having sex meant nothing, and never had... abandoning her dynamic of meaningless sex to better herself represented her character development. For the mother, it was about taking some time to just think about herself and do something to please herself, as opposed to being totally devoted to and thinking of nothing but her family... to be, in the teeniest, tiniest, smallest way a little bit selfish.

Outside things don't exist in the show's universe

• A rare in-universe example, all over the place with the show. Highlighted once they enter the show's world where the things never addressed in the show simply don't exist. There are no toilets, there's literally nothing outside of Pleasantville, and the residents don't even know what sex is. And of course, the entire world is actually monochromatic.
  • Out of universe: If there's nothing outside Pleasantville, where did the opposing basketball team come from? At the very least, without any roads leading out, how did they get in?
    • They're cross-town rivals.
    • Another explanation: they get in off-screen. The citizens know about the USA, they just don't need to go there.

Does the show's changes impact on the actors?

• How are the characters in the show treated as stand-alone if actors were portraying them when the show was originally made in the 1950s? Any sense to this?
  • What? Seriously, no idea what you're asking.
  • Because they're in the show's narrative universe. Think of it as stepping into a book — you're meeting the character, not the author. Thus, while actors may have come up with explanations for various things, their speculation never made it into the series — inside Pleasantville, anything that never appeared in the series simply doesn't exist.

Love Dodecahedron Ending

• Can someone explain the ending to me that happens between George, Betty, and Bill? Did Betty leave George for Bill, stay with George, or is she conflicted on what she wants? It's really confusing and I really want to know what it all means.
  • There is no answer to that question, it's purposefully left unresolved and even commented on in the movie (With each one saying they don't know what happens next). Along with getting all the benefits of real life like freedom and sex and enjoying food are the downsides of real life, and that includes things not being tied up neatly or people having a clear romance path. None of them hate each other, none of them is a bad person or somehow doesn't 'deserve' to be happy, they're just stuck in a situation with no easy or 'right' answer as they have desires and feelings now that they're working through. As it stands, not even they know what's going to come of themselves.
  • I thought she ended up with both of them, because they realized they can do whatever they want now. I just don't understand why they were both sitting in the same spot?
  • The ending is a bit of a Mind Screw in that it can be interpreted in a few ways. Are they working as a threeway now, or is Betty still having an affair with Bill? I doubt it's the latter, since the two don't seem to mind being open about it. Would the Pleasantville people even know what an affair is? Would they remain strictly monogamous or create some kind of free love society?
    • Or, like the vast majority of people from our society, they're just in the process of figuring it out. The husband and wife will probably separate for awhile but explore whether they can make or want to make their marriage work properly. Meanwhile the wife will continue to see another man she has feelings for. Eventually she'll probably choose one of them and settle down again.

Colorization through breaking patterns

• Why didn't the townsfolk who were smashing windows and burning books start to colorize? Surely that's just as profound a breaking of their pattern as falling in love or discovering a passion for painting.
  • It's not just about breaking the pattern, but how and why you break the pattern. The people smashing windows and burning books are trying to force things back into the pattern.
    • This explanation falls apart when you consider one of the last scenes, in the courtroom, where the mayor becomes colorized because he's the one trying the hardest to keep things the way they were.
    • That's not why he becomes colorized. He becomes colorized when he stops trying to hold back the changes.
    • Actually he becomes colorized when he lets himself feel anger.
    • This is the correct thing. The mayor was previously nothing but the "big, jovial, easygoing guy whose entire thing is acting like he cares about everyone (with a side of being a bit of an overbearing minor jerk for light jokes)" type. When he gets angry, but more when he admits to being angry about the changes and not caring about the people he's hurting, that's when he becomes colorized.
    • More to the point, the mayor becomes colorized when he is forced to stop resisting the need to fix the pattern.

Theme is Boomers ruining a utopia?

• So is this film basically an allusion of how boomers ruined society? Because if you ignore the obvious bias that the film shows towards most of the female characters compared to the male characters in Pleasantville and focus solely on the teenagers as a whole, you start to see the film starts portraying that not everything about the counterculture movements in the 50's to the 70's as a good thing. As Pleasantville literally starts falling into disarray.
  • It's more of a "things have to get worse before they can get better." Pleasantville represents a complacent society. In order for society to grow past it's complacency and allow individual freedoms, parts of that society have to be confronted, destroyed, etc.
  • Besides that, the oldest boomers were only 12 in 1958. They barely even existed in Pleasantville, or at least in the portions of it that we saw.

Impact of David and Jennifer coming to Pleasantville?

• Did David and Jennifer's intrusion forever alter those Pleasantville episodes? As in what we saw in the movie are what viewers in-universe are going to see in those episodes from now on. This may also confuse hardcore Pleasantville fans as well as any of the show's living creators or cast members not recalling doing any of that during filming. Could the alteration have worked retroactively making whatever happens in those episodes now as what they've always been?
  • The TV show is probably completely unaltered in its recorded form. The "Pleasantville" world that the movie takes place in is most likely some kind of Narnia-like parallel dimension that is based on and functions according to the rules of the television show, not the actual literal television show itself. My guess is that the remote control magically created a separate 'Pleasantville' dimension for the characters to inhabit, and no one else watching the Pleasantville TV marathon noticed anything different at all.
• Maybe like with Jumanji, only the people who encounter it are changed while the world inside stays the same for the next people to meet it.

No one in Pleasantville knew about sex?

• Why did no one know about sex when the town had a Lovers Lanes? We all know what goes down in places like that and the adults had to also, right?
  • Sex education was different back then and, besides, in The '50s people weren't exactly candid about their sex lives or the subject entirely.
    • Even if that's true, there's still a Lover's Lane which means sex existed. So why was sex treated like a new thing in that universe?
    • The rule of the thumb is the only things which had explicitly existed in Pleasantville before David and Jennifer were those which were explicitly shown or at least mentioned onscreen on the series as filmed in 1950s. And sex obviously wasn't. As for Lover Lane's purpose, well, you have to take them literally when they keep repeating the "holding hands" thing.
  • They were shown "holding hands" at Lovers Lane, it really is that simple.