Hilarious in Hindsight: "Pink Triangle" is about a straight man pining for a lesbian. As with the rest of the album, it's based on Rivers Cuomo's personal experience: he had a crush on a woman, but gave up on pursuing her when he saw a pink triangle patch (a gay pride symbol) on her backpack. It's only after he released the song that he learned that this was a case of Mistaken for Gay: the woman wasn't a lesbian herself, and only wore the pink triangle symbol to show that she's an LGBT ally.
Jerkass Woobie: The lyrics can produce this effect, as some of them which might invite more sympathy are contrasted with ones that come across as assholish (the third verse of "Getchoo", which undercuts its protest about being seen as a "freak" with an insenstively-worded dismissal of his behaviour as "just fooling around"), creepy (the sniffing-and-licking-a-Japanese-fan's-letter-and-imagining-her-in-her-school-clothes business of "Across the Sea", which really wrecks the chorus' vibe), stalkerish ("So I went into your room, and read your diary!" in "El Scorcho") or just plain what the fuck ("Butterfly"). Cuomo himself acknowledged this in a letter to the Weezer Fanclub in 1996.
Misaimed Fandom: A Zig-zagged version: Many listeners have described the album as "incelcore," due to its lyrics and the way the protagonist is around females. This is more or less a Vocal Minority that's mocked by the majority who point out the album's less angsting and social awkwardness, and more Cuomo's own Creator Breakdown when recording the album. (Plus, it's hard to imagine many incels relating to a song called "Tired of Sex.")
Squick: "Across the Sea", in which a then 26-year-old Cuomo admits to lusting after an 18-year-old Japanese fan by sniffing and licking a letter that she sent him, imagining her in her school uniform, and wondering how she masturbates.
Tear Jerker: The entire album qualifies, but "Across the Sea" and "Butterfly" are arguably the biggest ones.
Vindicated by History: One of the biggest examples in music. What was once a critical and commercial flop is now considered by many to be Weezer's best. To put it in perspective: In 1996, Rolling Stone readers voted Pinkerton the second worst album of the year. In 2002, Rolling Stone readers voted Pinkerton the 16th best album of all time.
Wangst: Some listeners may find it hard to sympathize with the lyrics of "Tired of Sex", which essentially whine about having too much sex.
What Do You Mean, It's for Kids?: While on tour for the album, they did an acoustic lunchtime show at a Seattle-area high school, as part of a contest sponsored by a radio station. Amazingly, they got away with performing "Pink Triangle" during the set.
Katawa Shoujo "Instafeels" video.