Tower Topper is possible to "win" by proving to Britney that the game is rigged and impossible to win by getting to the top line and showing how the block skips over the winning position. You can further "win" the game once Ai rigs it by not making any mistakes that expose how she's not just made the game winnable but impossible to lose. Each game is meant to be a thematic lesson of sorts, with this one highlighting not just Zach's unhealthy amount of prideful stubbornness is a product of an environment where he never had to compromise to avoid failure because someone was always around to protect Zach from facing any negative consequences (his mom, Keisuke, and now Ai), and he's never really acknowledged that outside help beyond resenting it.
Dance Uprising is winnable, but it's very hard. The high scores were set by someone I know who is really good at rhythm games, and what I made isn't a good rhythm game in that the notes had to be procedurally generated based on the peaks of the audio file which won't always line up with a beat. Its lesson is that Zach doesn't necessarily have to suffer consequences with experimenting with femininity if he can trust Britney enough to let her help or save him when he missteps, but he should still try to take middle approach of not being too enthusiastic nor too defiant.
Zone of the Zombies 2 is survivable, but I wouldn't call it humanly beatable. The speed you shoot at is far important than your accuracy, and while it might be possible to drop every zombie if you spam both mouse buttons like a demon, it's not a reasonable expectation. It's meant to be a lesson about being distracted with the wrong objective yet trying to conquer it by himself meant to tie into how Zach's goals with re:Dreamer, but more specifically how Zach sabotages himself when he tries to fight Britney to prove her wrong instead of teaming up with her as an equal partner.
Mrs. Puck Man isn't playable, and it isn't a lesson so much as it is a metaphor for many aspect of Zach's masculinity. He talks a big game about knowing way more about the cabinet than you would expect given the impression he exudes of never actually playing it. He feels upset when Britney offers to pay for it and can feel even more upset when she says "ladies first" as a dig. His forceful manhandling of it when he feels it isn't working can result in breaking part of it (the joystick being a further metaphor for the body part he no longer has and yes I have to word it like this for itch.io). Even if it's a relic of the past, he still feels bad about having broken it with a lingering sadness of disappointment for what could have been but never was. If he's played both Tower Topper and Mrs. Puck Man he can feel so bad that he will even go to the manager's office before he leaves and give back the expensive game console he won on the condition that they use that saved money to repair the cabinet instead of hauling it to the dumpster.
This was more than you asked, but I like giving details like this.