The Best Valentine's Day TV Specials From The '90s

by Amy Roberts

Since I spent most of my childhood absolutely devoted to all the best kid shows that the '90s could offer, I am a hopeless romantic. Seriously, nearly everything I know about love I learned from those formative Valentine's Day specials of '90s kids shows, and you know what? They've served me well. I strongly believe that part of the reason for that is because the '90s were an absolute golden era of quality programming for children.

These shows never pandered to or patronized their young audience, and as a result, some of the best Valentine's Day TV episodes from that era were so amazing because they dared to explore love as being more than just a disposable, gift-wrapped sentiment. Instead, these shows portrayed love in all of its beautiful, wonderful, tragic, frustrating, painful, and glorious forms. And damn, that was some powerful storytelling for a kid to drink in at such a young age.

And by doing so, these Valentine's Day specials reminded kids that our feelings were normal, no matter what our parents or school teachers told us at the time. However we all felt about our crushes or those first loves that we nervously grabbed the hands of at recess, those feelings were all totally valid. And every one of these episodes explored and celebrated that notion to its fullest.

1. Hey Arnold!


Episode: "Arnold's Valentine" — Season 1, Episode 20

Oh, boy. Hands up, anyone who could painfully relate to Helga's lovelorn, passive-aggressive passions in Hey Arnold? Ugh, me too. And in this episode, in which she pretends to be Arnold's French pen pal in order to score a date with him (it goes horribly yet sweetly wrong), my little childhood heart actually broke for her.

2. Boy Meets World

Episode: "First Girlfriends' Club" — Season 5, Episode 15

The favorite fictional boyfriend of many a woman's childhood, Shawn Hunter, is about to share Valentine's Day with his girlfriend, Angela. Except a gaggle of his most irrational ex-girlfriends kidnap him in a bid to stop him from inevitably sabotaging the day and his own relationship, just as he did theirs. It was completely ludicrous and I love it.

3. Sister, Sister

Episode: "Valentine's Day" — Season 3, Episode 16

Tia played cupid in this episode when she tried to help Tamera win back her ex, and, more importantly, help Lisa and Ray realize their true, potent feelings for each other. I can still remember, with absolute crystal clarity, the sheer anguish (and delight) involved in waiting for Lisa and Ray to finally couple up.

4. Clarissa Explains It All

Episode: "Clarissa's Crush" — Season 2, Episode 1

Not content with simply sighing dramatically and daydreaming to an *NSYNC album about her pre-teen crushes like the rest of us, Clarissa Darling tries to concoct different ways to meet her crush — local weatherman Flip Fontana. The whole episode is dreamy and obsessive and totally evocative of exactly how a crush felt at that same age.

5. Recess

Episode: "My Funny Valentines" — Season 3, Episode 12

In a direct protest to Valentine's Day, petulant rebel T.J decides to send out a set of grotesque anti-Valentine's Day cards to every girl in school. Except the protest completely backfires when the cards get misinterpreted as legit love notes and a whole host of hilarious reprisals happen. Man, I loved this cartoon.

6. Rugrats

Episode: "Be My Valentine" — Season 6, Episode 32

Is there anything cuter than a bunch of babies trying to find a valentine dog date for their pet puppy? I think not.

7. Sabrina The Teenage Witch

Episode: "First Kiss" — Season 1, Episode 17

Sabrina always excelled at delivering some absolute first class Valentine's Day episodes, but it was the show's very first Valentine's effort that I truly cherish. Showing Sabrina turning her boyfriend, Harvey, into a frog after they enjoy their first kiss, the episode shows her struggling to turn him back, and oh jeez, is it sweet.

8. The Adventures Of Pete & Pete

Episode: "Valentine's Day Massacre" — Season 1, Episode 9

Not only does Big Pete endure the embarrassment of having a blatant crush on his math teacher, but the school bully is also sweet-talking his best friend in order to humiliate him further. Oh, and a school mascot accidentally gets murdered. It all goes off big time, people.

9. The Powerpuff Girls

Episode: "Keen On Keane" — Season 4, Episode 11

The girls decide to do some matchmaking when they realize that their teacher has no Valentine's date. Except they set her up with Professor Utonium and the two fall so madly in love that it threatens the safety of the city. Which is always a legitimate concern for all of us, right?

10. The Simpsons

20th Century Fox

Episode: "I Love Lisa" — Season 4, Episode 15

You'll remember this one as the episode where Lisa feels bad for Ralph Wiggum and sends him a Valentine's card. Except he promptly develops a massive crush on her, and she ends up rejecting him and breaking his heart on television. As you do. I still can't think of the phrase, "I Choo-Choo-Choose You" without dissolving into a mound of sadness.

11. California Dreams

Episode: "My Valentine" — Season 4, Episode 2

When Tony and Sam celebrate their first Valentine's Day together, they also realize that it could be their last because Sam has to transfer back to Hong Kong soon. So, they do what any lovesick air of teenagers could do in such a scenario — they get engaged. Naturally, this news does not go down too well with their friends, but they get a great song out of it and it makes for great television, folks.

12. Clueless

CBS Television

Episode: "Secrets And Lies" — Season 1, Episode 18

OK, so the TV spinoff of the classic movie wasn't perfect, but it definitely had its moments of greatness. And this episode — which sees Valentine's Day sending Cher's head into a spiral and divulging one of Dee's secrets, while Amber deals with a secret admirer — is pretty damn lovable.

13. Beverly Hills 90210

Episode: "Bleeding Hearts" — Season 6, Episode 21

If your parents were anything like mine, then you probably weren't even allowed to watch this show as a kid. But this episode still deserves a mention. There's celibacy pledges, drug deals, shady secrets, and a major heart condition at play. And on top of all of that, it's also Valentine's Day.

I highly recommend swerving cupid this year and being your own valentine by treating yourself to a rewatch of any of these episodes. Trust me, they're all the romance you need.