15 Best Valentine's Day TV Episodes Of All Time

When you've got a full season's worth of episodes to write (back when shows used to run for longer than eight episodes a season, anyway), it can start to look a little daunting. Thank God for holiday episodes, right? With plenty to choose from, they offer an easy option to slide into a show's lineup. And Valentine's Day, especially if you've got characters audiences are desperate to see get together, makes for a guaranteed slam dunk. 

Whether these episodes feature comic misunderstanding, long-awaited pairings, loneliness on an epic scale, or even a murder spree, we just can't resist what these shows are serving up. And while some series may run dull Valentine's Day specials that audiences forget the minute they're off the air, the episodes we've assembled here are the best of the best, capable of winning over even the coldest, most cynical hearts. So swing by CVS and panic buy a sampler box of chocolates, because romance is most definitely in the air.

Despite the fact that "Hey Arnold!" was a kids' show on Nickelodeon, it still had its fair share of romance. Especially from Helga Pataki, whose brusque exterior belied a deep and poetic longing for a certain football-headed boy in her class. "Arnold's Valentine" throws a bone to all the Helga-Arnold shippers out there, as well as offering up a surprisingly mature take on what happens when you've spent so much time putting your crush on a pedestal that you aren't able to see them for who they are anymore. 

Helga tricks Arnold into going out to dinner with her, pretending to be his sophisticated French penpal. But that very same night, Arnold makes plans to go on a date with Ruth, the girl he's been crushing on hard for ages. In true sitcom fashion, he ends up bopping back and forth between the two, trying to keep his two dates straight. But along the way, he gets to know Ruth a little better — and that isn't necessarily a good thing. At the same time, he and Helga begin to have a great time. Who would have thought these two crazy kids might just make it after all?

"Futurama" is primarily a sci-fi comedy. Still, it has plenty of romance involved — although "Put Your Head On My Shoulder," the Season 2 Valentine's Day episode, is perhaps not the best example of it. 

In it, Amy and Fry end up stranded when her rocket car runs out of gas, giving the two the opportunity to bond and, well, hook up. But things get decidedly more complicated when their relationship hits the skids, they get in an accident that requires Fry's head to be grafted onto Amy's body, and they break up. (Yes, in that order.) So any future dating of other people in this episode becomes ... well, fraught with complication, to say the least. 

In terms of genuinely touching romantic affection, it can't hold a candle to some of the moments we're treated to with Fry and Leela. But when it comes to jealousy, comedic misadventures, and the deconstruction of romantic tropes, "Put Your Head On My Shoulder" has everything you could want and more.

Jim (John Krasinski) and Pam (Jenna Fischer), arguably the most beloved couple on NBC's "The Office," aren't even together by the time the Season 2 Valentine's Day episode takes place. Still, there's plenty of romance to go around. (Although to be fair, almost all of it is generated by Phyllis and her special someone, who nailed it when it comes to sending giant ostentatious Valentine's Day gifts to the office and making her coworkers turn green with envy.) 

Pam is still with Roy, and since they're saving money for a wedding, she told him not to get her anything too crazy for Valentine's Day, a decision she regrets right around the time that Phyllis's giant teddy bear is delivered. 

Meanwhile, Michael is in New York City putting his foot firmly in his mouth at a company meeting with Jan, as Dwight panics over what to get Angela after she surprises him with a Dwight bobble head. A classic ensemble episode, this one shows the strengths of its entire cast.

Despite the many romantic relationships that evolved over the course of "Buffy the Vampire Slayer," the classic '90s teen show only had one proper Valentine's Day episode during its run on The WB and, later, The CW. And surprisingly, its main focus wasn't on Buffy and Angel, the show's most iconic pairing during its early years — although to be fair, their relationship was at the time experiencing one of its notorious downswings, seeing as Angel is sadistic and soulless at the time. Instead, Xander (Nicholas Brendon) is front and center. 

Smarting from Cordelia (Charisma Carpenter) breaking up with him, he enlists resident witch Amy to cast a love spell on her, with the hopes of winning her back (albeit by shady means). But as one might expect, this all backfires. Instead, every single woman within a three-mile radius has the hots for Xander, with the sole exception of Cordelia. What follows is a horrifying yet wildly funny take on the "be careful what you wish for" parable, with the female population of Sunnydale all vying for Xander's attention — with increasingly dangerous (albeit hilarious) consequences.

One of the best things about ABC's "Modern Family" is how all three of the main couples are adorable in different ways, so any Valentine's Day episode this show puts out is destined to be extremely cute. 

"My Funky Valentine" doesn't let us down. Phil and Claire decide to celebrate the holiday with a night out, where they check into a hotel and indulge in a bit of light roleplaying in the lobby bar. But things take a turn when they decide to head up to their room, only to find themselves stuck on the escalator with Claire's coat — the only thing she happens to be wearing — trapped in the mechanisms. 

Classic "Modern Family" shenanigans. Although this is the first season and we're still growing to care about all of the characters, it speaks to the quality of the cast and the chemistry they had together that everything is hilariously perfect so early in the show's run.

The will-they-won't-they relationship between Fran (Fran Drescher) and Mr. Sheffield (Charles Shaughnessy) is one of the most enduring and enjoyable aspects of CBS' "The Nanny," so it makes total sense that a Valentine's Day episode with various romantic misunderstandings between the two of them would be a highlight of the series. This is what we get in "Love Is a Many Blundered Thing," which sees the two grappling with their growing feelings for one another. 

When Fran receives an anonymous Valentine, she assumes it's from Mr. Sheffield and, eager to reciprocate the sentiment, she predictably goes big, renting out an entire billboard asking him to be her valentine. The only problem? It was actually from someone else. Now, desperately trying to avoid looking desperate, she has to paint over the billboard before he sees the message. (A task made all the more difficult when she gets stuck up there and Sheffield has to come to her rescue.) Their easy, comfortable chemistry with each other makes this one an underrated holiday gem.

From the first episode of "Abbott Elementary" on ABC, it's clear that there absolutely needs to be something going on between Janine (Quinta Brunson), our peppy go-getter, and Gregory (Tyler James Williams), the substitute teacher. But in true sitcom fashion, they make us wait for it. By the second season Valentine's Day episode, we're still waiting, but we're definitely inching in the right direction, with at least Janine fully aware that she has feelings for Gregory. The problem? They're both dating other people — people who are extremely wrong for them, at least based on the gifts that they exchange on Valentine's Day. 

Gregory gets his girlfriend a Lego bouquet, since she's allergic to real flowers, but she's expecting something a little more high-end. Meanwhile, Janine is utterly nonplussed when her boyfriend gives her a fancy designer tote, something she immediately starts filling with school supplies. This mismatch is a cute way for the show to make it clear how perfect they are for each other, while still keeping the mystery alive. (For a couple more episodes, at least.)

Leave it to The CW's "Supernatural" to come up with a truly gruesome version of a Valentine's Day episode. In this Season 5 darkly comedic twist on the holiday, Sam (Jared Padalecki) and Dean (Jensen Ackles) are drawn to town when people begin finding increasingly extreme ways of showing their love. As in, killing each other as an ultimate act of devotion. Naturally, the Winchester brother assume that there's something supernatural afoot, and their first suspect is a rogue Cupid, who's taking the whole "making people fall in love with each other" thing a little too far.

But alas, our Cupid is just a ruby red herring — the real villain is Famine, of Four Horsemen of the Apocalypse fame. It turns out that their purview is not limited to hunger in the most literal sense but can be applied to things that people long for or crave. Like a romantic partner or, say, Twinkies. With this quirky yet genuinely horrifying Valentine's Day special, "Supernatural" pays homage to the holiday while also further developing the season's arc.

There's secondhand embarrassment, and then there's watching the perennially unlucky in love Peggy (Elisabeth Moss) mistakenly steal a bouquet of flowers from her assistant Shirley, believing them to be hers, only to lash out irrationally when she learns the truth several hours later. Nothing like AMC's "Mad Men" to make you want to bury your face in a blanket and curl up in the fetal position out of sheer cringe.

"A Day's Work" is one of the show's rare Valentine's Day episodes, and while there are plenty of plotlines going around, what most people remember is Peggy making every possible wrong move. From blaming Shirley out of misdirected anger at her own mortification to calling Ted — her married ex-lover who moved 3000 miles away from her to get a fresh start — in order to reject the flowers he didn't even send her, our girl is not at her best here. But hey, who hasn't had one of those Valentine's Days?

Not too many holiday specials on television end up creating an entirely new holiday (off hand, we can think of Festivus from "Seinfeld" and Chrismukkah from "The OC"), but NBC's "Parks and Recreation" joins this elite roster with "Galentine's Day." Created by Leslie Knope (Amy Poehler) as an opportunity to celebrate all the wonderful women in her life, Galentine's Day takes the focus off romance and honors a different kind of love — friendship — and that's something we can all get behind. 

Of course, the episode does dip at least a few tentative toes into the world of romance, as Leslie attempts to reunite her prickly mother (Pamela Reed) with a long-lost love played by John Larroquette. Unfortunately, some flings are better left in the past, as they both quickly realize when he fails to live up to the rose-colored recollections of young love. (Honestly, it kind of reminds us of what would happen if Baby and Johnny from "Dirty Dancing" were to run into one another in their early 60s.)

Summer (Rachel Bilson) was never intended to be a main player on the Fox teen drama "The O.C." But her charm and crackling chemistry with Seth Cohen (Adam Brody) made her an immediate fan favorite, keeping her around for the entire series run. Although their relationship had plenty of ups and downs over the course of the show's four seasons, it takes off with aplomb in the Season 1 episode "The Heartbreak." 

It's Kirsten Cohen's favorite holiday (much like Seth's is Chrismukkah), but no one else seems to be in the holiday spirit. Ryan and Marissa are still recovering from the whole Oliver debacle, and the recent presence of Ryan's ex Theresa isn't making things any easier. After Seth and Anna break up, that leaves the door open for him and Summer to get together — and they do, multiple times, although it must be said that the first isn't exactly magical. But that's part of what makes this Valentine's Day episode so endearing. We have two couples who clearly care about each other but are trying to find their way through the weeds, as it were. 

Say what you will about the later episodes of the show, but the first season — and especially its Valentine's Day special, now that we're finally free from Oliver — are as close to perfect teen drama as it gets.

The bread and butter of Fox's "Bob's Burgers" is its holiday episodes. They have half a dozen for every major holiday and even created a catchy new Thanksgiving tune for the turkey-fest that just doesn't have enough songs devoted to it. So naturally, it has more than a few top-notch Valentine's Day specials. The question becomes not whether "Bob's Burgers" should make the list, but which of its holiday episodes should be included. 

In the end, we went with "The Gene and Courtney Show," partly because Gene's gentle yet chaotic energy gives him some of the most endearing preteen romances, and partly because Courtney is a queen and one of the show's unsung heroes. By the time that they're discovered and offered the primo gig of doing morning announcements, they're already well past their short-lived relationship. But that doesn't mean that working together doesn't stir up some old feelings. 

In the episode's wildly entertaining B-plot, Tina is put in charge of the school's carnation fundraiser, only to face an unexpected hitch when she goes feral tearing all the cards open to see if anyone got her flowers. Unfortunately, now she has no idea which card goes with which envelope. Whoops. Funny and genuinely sweet, "The Gene and Courtney Show" is a showstopper.

Ordinarily, Valentine's Day episodes are all hearts and flowers. But in the Season 6 episode of "ER," "Be Still My Heart," the traditional shade is a bit more blood red than usual. Although the show had plenty of light-hearted holiday episodes, "Be Still My Heart" took things in a dark direction, where a mentally unstable patient (David Krumholtz) is held in the emergency room while awaiting a psychiatric consult. 

While the staff Valentine's Day party rages on, John Carter (Noah Wyle) is met in a dark room by the patient, armed with a knife, who stabs him multiple times in the back. As he falls to the ground, he sees the dying body of Lucy, an intern with whom he had a sometimes antagonistic but ultimately caring relationship. One thing's for sure: The staff writers of "ER" did not come to play when they came up with "Be Still My Heart." "It sounds trite, but I have almost total recall about certain aspects of that show — and that storyline, in particular. I remember every moment," Wyle said of his experience filming "Be Still My Heart" in a 2025 interview with TVLine.

Loveable, quirky elementary school teacher Jessica Day (Zooey Deschanel) starts the first season of Fox's "New Girl" in a bit of a romantic funk. The pilot sees her break up with her long-term boyfriend Spencer, who has been cheating on her, and she hasn't fully recovered by the time the show's first Valentine's Day episode rolls around. Still, she's determined to give the single life a try and commits herself to having a one-night stand, despite the fact that every fiber of her being is hardwired to form an emotional connection with any prospective romantic partners. 

And predictably, when she zeros in on Oliver (Ryan Kwanten) as a potential target with whom she has absolutely nothing in common, things go awry almost immediately. This episode of "New Girl" has everything we love about the show boiled down into a single half-hour: Jess making poor sexual decisions, Schmidt struggling in his constant battle against youths, and Nick offering up more of his law school lore. It's still early days for "New Girl" in "Valentine's Day," but the show is clearly already firing on all cylinders.

"I Love Lisa," the Valentine's Day episode of the fourth season of "The Simpsons," proves yet again that one of the show's greatest strengths was its ability to mock characters while also making audiences empathize with them. It all begins when the well-intentioned Lisa (Yeardley Smith), seeing that her classmate and one of the show's most frequent punching bags Ralph Wiggum (Nancy Cartwright) hasn't received any Valentine's Day card, hastily addresses one of her own to him. 

But this kind gesture arguably does more harm than good — Ralph becomes besotted with Lisa, and when she finally has to let him down, well ... as Bart points out, on the video replay you can actually see the exact moment where his heart splits in two. Because Ralph is such a likeable character and Lisa such a genuinely kind-hearted one, the episode comes across as endearing rather than mean-spirited — the sweet spot of peak "Simpsons."