Based on the manga by Komiya Sanae and Nonomura Hideki.

What are some cringy moments in anime?

Well, I have two scenes that come to mind.
First: Almost any scene from Eiken. This anime was just one big cringe-fest in my eyes, almost every girl has breasts that are way too big (I mean, look at that pink haired girl in the bottom corner), there are so many sexual scenes that try so hard to be funny, that it just comes off as annoying, inappropriate and overall, just makes me feel very uncomfortable, especially when most of the girls have these raunchy quirks that try to come across as uniquely humorous, but most of time it’s just irritating! Especially when it comes to Yuriko, who constantly jumps up and plants her crotch into the protagonist’s face. Fortunately, there are only two episodes of this show, the second one being worse than the first, in which the school participates in these “sports events” (Since when has “yogurt water-sliding” become a sport?).
There is so much wrong with Eiken that I can only suggest you watch it for yourself to see how awful it is, now for the other scene, which is something that happens at the very start of Eiken. As Anime America describes it: The Perceived Pervert I don’t think I can put up a picture of what this is, but in a nutshell, it’s when a male character (usually the protagonist) falls or slips on top of some female character and accidentally touches her breast(s) or crotch.
Suddenly, the female character starts kicking the male character’s ass, because she feels justified in putting down a supposed pervert, after an accident. This scenario needs to stop, for very simple reasons.
First of all, this is something that only ever happens that regularly in anime, and I never understood why that had to become a repeatable scene in the first place.
Second, it perpetuates this stereotype about women that they can abuse men without any repercussion, since if it were the other way around, the male would undoubtedly face punishment for abusing a woman from what was clearly an accident.
I could go on about how this scene pisses me off, but I think you all know about it by now.