I feel you. This is how I feel about teen movies made before the 90s - The Breakfast Club, Dazed and Confused etc. I just can't empathize with that period (the 80s, 70s...) because I was born at the middle of the 90s in Europe and I didn't have exposure in my own adolescence to the things depicted in those films. However, I can empathize with teen films made after the 90s, especially the 2000s, because they're closer in time to my own adolescence and I might have experienced some similar situations.
'The Perks of Being a Wallflower' is kind of an odd one because it's a 2010s film and the plot is supposed to take place in the 90s (20 years gap in time) but it somehow works that way. Perhaps the 'hipstery/instagramy' thing comes from the fact that they used a filter over the film to make it appear older than it is and fade the bright colors that we see in films nowadays (stylistic effect). The plot is much clearer in the book, but it mainly concerns Charlie getting over a lot of things that happened in his life, and the main themes are child abuse (Charlie was abused as a child by his aunt, his aunt was also abused as a child and as an adult by her boyfriends, Sam was also abused as a child by her dad's boss, Brad was physically abused by his dad for being gay etc.) and mental health issues (Charlie's depression following his abuse and the death of his abuser i.e. his aunt). They merely gloss over these to keep the PG-13 rating - if they divulged or explained more explicitly what happened to the characters, the film would've gotten NG-17. The film obviously isn't about getting into pretty Sam's pants!
It's very, very possible that they didn't know David Bowie's 1977 hit Heroes if they were teens in the 90s. I didn't know Heroes until the 2000s, because that's when I started becoming a teen and developing a taste in music.
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