Would it be hard for a movie like Never Been Kissed to be made today?
For starters, social media would likely make it harder for Josie's undercover scheme (and for people to not more quickly uncover her real idenity) to work. Plus, I find it hard for people to quickly digest Josie's romance with Mr. Coulson (leading up to the climatic "kiss") simply due to the unfortunate implications behind it. It's kind of like in Clueless where Cher winds up with Paul Rudd's character and we're supposed to ignore the fact he's virtually her brother (ex step-brother but still...)
http://recapscallion.blogspot.com/2010/05/never-been-kissed.html
https://www.thelist.com/113889/never-kissed-things-adults-notice-90s-rom-com-classic/
https://www.refinery29.com/en-us/2019/04/229220/never-been-kissed-anniversary-teacher-student-relationship-controversy
Mean Girls probably made it harder to take the earnesty of this film seriously. That scene where that girl who vaguely looks like Drew Barrymore, crying about her "feelings" seems like a direct shot at Never Been Kissed:
https://www.youtube.com/watch?v=sR528E5_8yI&t