Do you have a friend who’s still stuck in high school? I know one too many people who are.

It’s a comment in passing. A sly remark. Looking people up on social media. Wondering about too many what ifs. Holding grudges against people who don’t deserve it.

For better or worse, high school remains as a significant time for some people. They remember it all a little too well. Even sometimes, wistfully thinking. Wondering. Wishing.

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There are several things that come to mind when I think back to school, and it’s not so much about the people.

Jansport backpacks. Lunchboxes. Yellow pencils and classic pink rubber erasers. Crayons and glue. The weather is fairly sunny, slightly breezy. Lockers. Cafeterias. Tennis shoes. School dances. Field trips. All the makings of your classic high school experience.

So today, we will transport to an idealized version of high school. In this Universe, maybe Chad/Stacy does text you back and take you to prom.

Drive Me Crazy (1999)

An underrated 90’s romcom classic! Such great chemistry between these two. Melissa Joan Hart breaks the “popular mean girl” trope by being one that actually has a heart. I’m actually a sucker for popular girl meets unpopular guy and this hits the spot perfectly. Adrian Grenier is actually pretty cool in his own right, he’s just opinionated and chooses to be different, which is a refreshing take on the character. This movie is peak 90’s teen nostalgia, outfits, music, comedy, romance, and all.

American Pie (1999)

How can I reference a Taylor Swift song in the title of this post and not put this movie on this list? I actually prefer the second one since it takes place at a lake in the summertime, but the first one is close behind and is pretty much comedy royalty.

She’s All That (1999)

A cult classic. This is one of the movies where you can show it to anyone of any age, of any generation, and they’ll just love it. Absolutely eat it up. It’s a classic “am I just a bet to you?” moment. So seemingly simple, yet unmatched.

Can’t Hardly Wait (1998)

Have you ever tried confessing to someone at the very tip of the high school experience? I’ve always wondered about couples who get together their senior year. The timing just sounds awful. Perhaps it’s the ticking time bomb of it all – a now or never adrenaline rush that finally pushes people to do what they’ve always wanted to do.

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It’s probably no coincidence that three of these movies were released in 1999, and the fourth one released in 1998. What a time the 90’s were for a so american high schooler.