First Time Watching: Clueless

Over the last seven years, I’ve watched shows like: The O.C., One Tree Hill, Gossip Girl, and Gilmore Girls. It has been eleven years since I was in high school, yet those shows forced me to look back at my experience through a different lens. I felt like I was finally understanding everything that happened, all these years later.

The movie, Clueless, made me feel the same way.

What I’ll do is give you a brief synopsis of the movie, name some of the key characters, and then talk about the moments that stood out to me. Hopefully, this will reveal the entire movie in front of you.

If it doesn’t, don’t say anything.


Clueless is a 1995 film based in Beverly Hills and is about a high school girl named Cher, who thinks she has everything figured out and can negotiate her way out of anything because her Dad is a lawyer and taught her to “never take the first offer”. While playing matchmaker for “clueless” classmates and teachers, she realizes that she is the one who is clueless. And then she kissed her former stepbrother.


Cher: She likes to (forcibly) help others find their perfect match, while trying to ignore the fact that she’s single. She also can’t drive to save her life.

Josh: He is Cher’s former stepbrother and is in college. He is played by Paul Rudd, so I’ll probably be referring to him as Paul Rudd most of the time.

Mel: Cher’s Dad. He’s very protective of his daughter, but not so protective of his diet.

Dionne: Cher’s (best?) friend.

Murray: Dating Dionne.

Tai: New girl at school, who is clueless. Cher takes her under her wing, until she becomes the most popular girl at school.

There are more characters, but I’ll talk about them as I mention them.


The opening video montage, which is set to “Kids in America”, has a very Rebecca Black “Friday” feel to it. The aerial view of the Jeep is to blame for me making this connection.

We’re introduced to Dionne, who looks like she is wearing a two-layer fondant cake on her head, but it’s actually just a hat rich high school kids wore in California in 1995, I guess.

Murray walks around with his pants halfway down his butt and his boxers sticking out. If you were in a school setting at any point in the last 30 years, you’ve seen this “look” on multiple people and probably asked yourself, “why?”

Cher got a C in Debate Class and when her Dad asks to see her report card, she says it’s not ready yet because the teachers were trying to lowball her with their “first offer”.

If I knew grades were negotiable, I’d have complained to my Grade 4 teacher about a C+ in algebra. I always did well in math; I had no memory of poor test results.

Heck, I couldn’t even tell you what algebra was at the time! All I knew was “math”.

Cher determines that her Debate Class teacher, Mr. Hall, is a miserable man because he’s 47 and single, so she tries to set him up with the World History teacher, Ms. Geist, by writing a poem to him and leaving it in his mailbox.

Within no time, those teachers were exchanging numbers on a bench and kissing in the staff parking lot. I feel like a paragraph was written into all future Code of Conducts because of them.

Now that the teachers were happy, they both bumped her grades up to an A-. Cher’s Dad was so proud.

Tai is the new girl at school and Cher takes her under her wing almost as a pet project, molding her into who Cher thinks she should be.

Cher tries to set Tai up with Elton, but Elton actually likes Cher. On their way home from a party in the valley, Cher rejects Elton, so he leaves her in a Circus Liquor parking lot.


What? The guy took her phone and then told her to lay down on the ground, so he could run away. Cher got up almost immediately and was more upset that her outfit was dirty.

This moment in the movie stuck out like a sore thumb and I don’t think it was necessary. She was already stranded in the middle of nowhere and was going to call Paul Rudd to pick her up, regardless.

It’s not like she struggled to find a phone, either. A payphone was right there.

The cops were never notified of the maniac with a weapon, roaming the streets.

Christian is a new guy at school and he looks like he stepped out of one of those cheesy posters that advertise a haircut style.

He’s overdressed, as evidenced by his pleated pants.

Cher likes him and decides to send herself flowers, love letters, and candy every day, so Christian thinks she is a hot commodity.

Do girls actually do this in real life? Is this a tactic you don’t want guys to know about?

Well, it worked on Christian. He takes her out to a party, but lo and behold, Paul Rudd is there to “keep an eye on Cher” because he’s liked her ever since his first scene in the movie, but she needs about 80 minutes to figure it out.

I forgot to mention that Cher’s Dad, Mel, threatened to kill and bury Christian if anything happened to his daughter.

Mel is basically every Dad on The Bachelor from the early seasons. I may be exaggerating here, but only a little.

Cher said, “Whenever a boy comes over, you should always have something baking.”

I mean, as someone who can sniff out food like I’m a four-legged member of the K-9 unit, I don’t hate that idea.

A theme throughout the movie is Mel’s health. Cher is always trying to get him to eat healthy and likes to say, “It has Vitamin C!” as if that helps.

There was a scene where she took a sandwich out of his hands and in that moment, a Sub got its wings.

Tai is at the mall talking to two guys she met at Foot Locker when, all of a sudden, they pick her up and pretend as if they’re going to throw her over a railing.

What the heck?

Of course, everyone at school talks about it and the story has been put through the broken telephone so many times that kids think a gang member tried to shoot Tai at the mall.

This gives her a lot of attention and she embraces it by retelling the story in a more harrowing manner than necessary. She is now popular and Cher is looking at her like, “How’d she get so confident so fast?”

Cher goes for her driving test and when she tries to change lanes, she nearly hits a bicyclist. To compound the issue, she hits a parked car on the side of the road and keeps driving!

The driving test examiner didn’t even tell her to remain at the scene. Instead, they keep going and he has her pull over…eventually.

She failed her test and is shocked she can’t talk herself out of it.

This brought back memories of my driving tests. Not because I did anything wrong; I passed them on the first try. It’s just a stressful ordeal.

Tai is burning things that remind her of Elton. She tells Cher that she loves Josh (Paul Rudd) now. This bothers Cher, but she doesn’t know why.

It’s because she loves him – her former stepbrother – but doesn’t realize it yet.

This sparks something in Cher and causes her to become a better person by cleansing her soul. Her days of meddling are over.

Eventually, Cher ends up with Paul Rudd and they kiss.

The whole “I love my former stepbrother and now we’re a couple” thing was a bit weird for me. And the fact that she’s 16, while he’s a freshman in college, also didn’t jive.

Oh yeah, Mr. Hall and Ms. Geist ended up getting married and invited a lot of students to the wedding. That’s not normal.

What I took away from this movie is that we’re all clueless at one point or another. We’re wrapped up in our own world, unaware of certain things going on around us, because we’re focussed on what we want.

As we go through the ups and downs of life, what we want changes and we lose a bit of our cluelessness every time we discover something new.

This movie wasn’t meant for me, though I’m a little less clueless after watching it.

See what I did there? Or are you clueless?

Two puns. Sorry.

Have you seen Clueless? Let me know your thoughts on it. How was your high school experience? What should I watch next?

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14 Responses to First Time Watching: Clueless

  1. Yyyyyyaaaaaassssss PAUL!!! I love this movie! Back when renting movies was a thing, I got this movie so many Fridays in a row my parents forbid me to get it anymore and to “try something new” but I loved the tv show and I needed the movie all the time!

    Its based on Jane Austen’s “Emma” actually LOL

    The dating the step brother was an issue for me. Not the age difference – girls are always into older guys. And yes, some girls DO send themselves flowers/cards/candies to make a boy jealous or think someone else is into her. Think of the “they want what they can’t have” or “if they know someone else is interested they’ll find you interesting too”

    Oh man I think I need to watch this today!

    Liked by 1 person

    • Paul says:

      I’m just picturing you wandering into Blockbuster and going to the same shelf every Friday and being like “THIS ONE” haha

      This is good info to know. Never would’ve imagined they would buy themselves something and pretend it’s from someone else. Girls are ahead of the curve. Took me 15 years to catch on lol

      Liked by 1 person

      • HAHA oh not even Blockbuster “Steve’s TV” 😉😉

        Lol and yeah man, girls are sneaky and we plan things. Like *sends a text we meant to send* then texts “hahaha oh my gosh I’m sooooo sorry that was for my other friend!”

        Liked by 1 person

  2. Sabrina B says:

    Yayyyy you watched it!! This is one of my favourite movies (I could quote every moment you mentioned off the top of my head) and Cher is one of my favourite characters. I don’t really think you’re the main demographic but there are funny moments all the same. The robbing moment is necessary because it taught me what an Alaia was, and I know now it’s a totally important designer.

    I saw this movie for the first time long before high school, and I think I wanted this to be what my high school experience would be like while also knowing it would not be like this. As you know, it was definitely not like this, except for maybe seeing dudes around me in sagging pants. Cher was and still is a fashion inspiration though.

    OH and when I was in LA in 2014 I drove past the house they used as her house in this movie, and it’s amazing.

    Liked by 1 person

    • Paul says:

      Haha your justification for the robbery is great. I never thought twice about that dress.

      That sagging pants era debuted in Grade 7 I think and carried on until the end of high school. I never understood it.

      But anyway, I think this is why girls are probably more aware/ahead of the curve at that age – you have movies and TV shows that show you what you can be in high school. Guys don’t have that. For me, Grade 9 was just school in a different setting. I didn’t understand the context of being in high school. This movie, and ones like it, should probably be required viewing on the last days of Grade 8 when there’s nothing to do, but I’m sure school boards will disagree with me.

      You would drive past the house lol

      Liked by 1 person

      • Sabrina B says:

        I think a lot of the 90s and 2000s high school comedies marketed towards guys have a much different focus–think Superbad or American Pie for example. Meanwhile things like 10 Things I Hate About You or She’s The Man have male leads as well as female leads and show male connection an bonding during high school, but get largely marketed towards girls. Basically: everyone should watch more movies.

        It wasn’t even on purpose! It would be if I went back though.

        Liked by 1 person

  3. peckapalooza says:

    As someone who went to high school in the 90s, I’ve always felt like this is a movie I should have more of an attachment to than I actually do. I don’t know… it just never did much for me. I know my sister loved it, though.

    Liked by 2 people

  4. Belladonna says:

    This movie is horrible! LOL

    Liked by 1 person

  5. rebbit7 says:

    I watched this film a while back. While I thought it was entertaining, I found the plot so bizarre and incongruent that I didn’t love it. Your play-by-play of the film confirms that! 😆 I also found it really uncomfortable that Cher ended up with her stepbrother in the end (incestuous much?), and I’d like to believe it’s all just satire. But it’s an American teen classic, so I guess I respect that! Can’t wait to see what else you review soon. 😊


  6. Dutch Lion says:

    This was Brittany Murphy’s debut if I remember right. I’m sad she died. She was awesome. I love her and Ashton Kutcher in “Just Married”. Really sad.

    Liked by 1 person

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