Eight Lessons Clueless Can Still Teach You About Dating

Enduring wisdom from the Alicia Silverstone classic on its fifteenth anniversary.

Alicia Silverstone in Clueless

By James Brady Ryan

Fifteen years ago this month, director Amy Heckerling gifted us with the iconic ‘90s teen comedy, Clueless. Some of the Valley-Girl speak may have faded from style, but this seemingly vapid film can still teach us some enduring lessons.

1) Do Not Mess With the Recently Single

Brittany Murphy and Jeremy Sisto in Clueless

We admire Cher for trying to help Tai find the most popular guy to date, but how did she possibly think that Elton was the right choice? She had a reason — Elton had just broken up with his girlfriend — it just happened to be a horrendous one. A recently heartbroken guy is the worst possible candidate for your new friend. Is he looking for a little rebound sex to help deal with the pain? Sure, maybe. A serious relationship with the new girl in town? No, he is not. Keep in mind, much like wild animals, people are at their most dangerous when wounded.

2) Be Wary of the Overly Affectionate

Jeremy Sisto as Elton in Clueless

Do you have a "friend" who likes to give you shoulder rubs for no reason at all? To plant kisses on your cheek just because you did a good job? Is he always orchestrating ways to get you alone in a car/elevator/walk-in closet? It takes the viewer about one minute to realize that Elton wants to hook up with Cher, not Tai, but it doesn’t occur to our protagonist until after Elton tries to stick his tongue down her throat in the parking lot of some off-brand 7 Eleven. Remember, if he buys you little presents when it's not your birthday, or offers to watch your cat even though his allergies will make his face puff up like a Shar Pei, he wants to make out with you.

3) For the Love of God, Make Sure It’s a Date

Justin Walker as Christian in Clueless

For a girl who’s apparently super popular, Cher is surprisingly bad at picking up social signals. There is no scene more painful and hilarious than her attempted seduction of her (unknown to her) gay friend, Christian. There are campy cinematic classics, a pratfall off of the bed, a lie about a stomach ulcer, and overtones of desperation. We can't imagine a more awkward moment for both parties than when someone asks you, “Wait, is this a date?” Your date will feel like a bastard, and you will feel the need to stay away from sharp objects until the embarrassment fades. When dating, make your intentions clear, in advance.

4) Let Them Come To You

Alicia Silverstone in Clueless

Cher is a true master when it comes to getting a guy’s attention. Her helpful hints include: don’t go up and talk to that guy you like the moment you see him; don’t immediately open your door for him (or for yourself, if possible); do send yourself flowers and candy to make sure you look popular. Are some of these rules a little crazy? Yes, (we'd really advise against the flowers thing) but they have a purpose. As hard as it can be, playing it cool works.  Next time you feel like flying past your crush in a hot-air blimp that says "I'm Available!" on the side, breath deeply and try to channel Cher. 

5) Nice to Meet You. Will You Marry Me?

Stacey Dash and Donald Faison in Clueless

Remember when Dionne yells at her boyfriend for shaving his head before their yearbook photos, because, in her words, “What will I tell our grandkids?” Or how the movie ends with the three main couples — two of which have only just started dating — at a wedding, joking about how soon the girls will want to get hitched? That was weird. It might have been less weird had the couples been older, but there has got to be some kind of minimum timeframe before talk of future offspring starts. Clueless is an example of what not to do here, unless you want to forever be known as “That guy who asked if I liked the name ‘Rebecca,’ for a girl, on the third date.”

6) Find Me a Find, Catch Me a Catch

Alicia Silverstone, Stacey Dash, and Wallace Shawn in Clueless

These days, it’s pretty weird to be set up on a date by someone else. In general, when your aunt Linda says she knows the perfect guy/gal for you, shrugging it off seems to be the best bet. But can your aunt really be that much worse than some random website that compares keywords in your online profile? It’s true that not all of Cher’s attempts to hook people up ended well, but she set up a couple who eventually got married. So the next time a friend or family member tries to act as your own personal Yente, consider saying yes. It’s got to be better than vainly searching through Craigslist Missed Connections, right?

7) Berets Are Terrible

Alicia Silverstone in Clueless

Maybe you think you can make it work with a very specific outfit; you’ll look French, or like a Beat poet! It’s kicky! No. Not even Alicia Silverstone gets away with this. Put it away.

8) Learn to Let Go

Alicia Silverstone and Stacey Dash in Clueless

Does that sound trite? Let me tell you a little story: once, there was a wonderful little comedy based off of a Jane Austen novel that captured a moment in time and hit the right chord with the right audience. It was so quotable! The cast was so cute! Everyone was very pleased. Then, they made it into a sitcom that was sad and painful and limped along for three years on ABC and the UPN until it was mercifully taken out back and put out of its misery. Or our misery. Whichever. But what was true for Clueless is true for your dating life: if something’s done, let it be done. Otherwise you’ll find yourself months after a breakup, clutching your ex's forgotten T-shirt and singing “All By Myself” to a bottle of wine. And no one wants that.

Commentarium (15 Comments)

Aug 23 10 - 12:58am

I think the beret looks just fine on her, especially the kind you'd find in a second hand store.

Aug 23 10 - 10:23am

I rewatched this recently and remembered why I loved it so much. One of the best teen movies of its era. I had totally forgotten about the Christian situation--how painful!

Aug 23 10 - 10:29am

#5: They're in high school. While a few of my friends in high school were realistic, most of my female friends were absolutely convinced that they were going to marry their high school sweetheart and spend the rest of their lives with them.

In all fairness, about half of them did. And they're still living in that same town doing crap jobs.

Aug 23 10 - 10:49am

Sad to see Brittany Murphy--real loss

Aug 23 10 - 11:19am

I think something's wrong with this page -- I keep clicking through from the Nerve homepage and winding up on Cosmo.com.

Aug 23 10 - 6:03pm

"Woman, lend me fi' dollas." Love that movie, love Cher's beret.

Aug 23 10 - 6:30pm

Legs crossed towards each other? That's an unequivocal sex invite.

Aug 23 10 - 7:36pm

Hey. I pull off a beret amazingly. And there's nothing wrong with a beat poet. I have been in a situation in which I thought I was on a date with ridiculously sexy gay guy. He;s still a friend, but I think I did pull an Alicia that night...

Aug 23 10 - 7:47pm
robert paulsen

stacy dash is still dangerously gorgeous.

also, i had a girl ask me about names for our baby on our second date. i should have taken this advice.

Aug 24 10 - 12:22am
In Bed

#9 You can't go wrong with Paul Rudd.
In Bed With Married Women

Aug 24 10 - 2:08am

Never thought the tv show was thaaat bad.

Aug 24 10 - 9:27pm

Re: #3, to be fair to Cher, when setting up that evening, I'm pretty sure Christian said something along the lines of "it's a date."

Aug 25 10 - 10:15am
souf shin

i wonder ?

Aug 26 10 - 11:53am

Okay, I can agree with everything said here, except the part about the berets. But maybe that's just because I'm a bit of a Francophile.

Sep 02 10 - 8:12pm

Do you actually mean "Lessons Jane Austen's Emma can still teach you about dating?" since Clueless was clearly based on Emma?