15 best Valentine’s Day TV episodes of all time

We choo-choo-choose the greatest February 14-themed installments to grace the small screen

By Saloni Gajjar, Jen Lennon, Cindy White, Jenna Scherer  |  February 8, 2024 | 1:00pm
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15 best Valentine’s Day TV episodes of all time
Clockwise from bottom left: Parks And Recreation, Arrested Development, The Simpsons, Futurama (Screenshots: YouTube) Graphic: Rebecca Fassola

February 14 is just around the corner, people. Which means it’s high time to rewatch those Valentine’s Day-centric TV episodes, whether they toast the holiday, revel in its craziness, poke fun at it, or what-have-you. From Michael Scott’s tour of Times Square in The Office to a survey of what love actually is in Orange Is The New Black to the greatest card of all time on The Simpsons, these are, in chronological order, The A.V. Club’s favorite Val-Day-focused TV installments to date.

This article originally published in 2023. It was updated in February 2024.

The Simpsons, “I Love Lisa” (1993)
I choo choo CHOOSE you

“I Love Lisa” is a fantastic example of showing its softer side. The episode boasts that famous “I choo-choo-choose you” valentine, the one Lisa gives to Ralph when she notices he hasn’t gotten any from the rest of their classmates. Ralph, of course, develops an instant crush (“uh, so, do you like…stuff?” remains iconic), and Lisa spends most of the installment trying to figure out how to let him down gently. The series would later offer a more cynical take on Valentine’s Day in season nine’s “Trash Of The Titans,” in which a department store owner invents “Love Day” to boost summer sales (and winds up creating a lot of trash). But our heart always goes back to this one. [Cindy White]

Buffy The Vampire Slayer, “Bewitched, Bothered, And Bewildered” (1998)
Buffy The Vampire Slayer - (2x16)

Let’s face it: The proto-incel vibes of early series Xander Harris have not aged well (kind of like those of his creator, ). But this season-two episode from staff writer Marti Noxon, which puts Xander in the spotlight for the first time, marks a vital moment of character growth for the third Scooby. It’s also, like some of the best Buffy episodes, funny as hell. Smarting over Cordelia putting the kibosh on their budding relationship (“Do you know what’s a good day to break up with somebody? Any day besides Valentine’s Day!”), Xander blackmails Sunnydale High’s resident witch, Amy, into casting a revenge-motivated love spell on his ex. Naturally, it backfires in spectacular fashion, causing every woman in town except Cordy to become infatuated with him. Does Xan slow-mo strut down the school hallway to the tune of Average White Band’s “Got The Love”? Does Amy turn Buffy into a rat that Oz has to rescue from a mousetrap? Does our hapless hero attempt to barricade himself and Cordy in the Summers’ basement, only to discover that the door opens from the other side? That’s a definitive yes to all of the above. And like the best of , the comedy is offset by meaningful character moments. Xan’s painfully honest speech to the spell-addled slayer (“If I thought you had one clue what it would mean to me … but you don’t. So I can’t.”) belies his usual objectifying advances; and we feel profound sympathy for Willow who, when not under a stalkery spell, is actually in unrequited love with her BFF. But the bloody cherry on top of “Bewitched” is when Angelus, in a bid to one-up Spike, gifts Drusilla with a literal human heart. Now that’s called making an effort. [Jenna Scherer]

Frasier, “Three Valentines” (1999)
Frasier - Niles Crane - ‘Three Valentines’

Sorry, Buster Keaton. David Hyde Pierce has come to snatch the 20th-century slapstick throne. In this serialized episode (widely considered to be one of ’s best), Pierce delivers arguably the greatest silent slapstick sequence of all time as Niles’ preparations for a V-Day date begin with ironing his suit and end with him, pantsless, dousing a sofa fire with a gallon of boiling-hot soup. The scene also gives Eddie the dog the chance to deliver Jim Halpert–caliber reaction shots. Frasier isn’t faring much better, as he desperately struggles to figure out whether a dinner with a PR exec (played by the great Virginia Madsen) is a date or a business meeting. And congratulations to Daphne for coming out on top when her lonely hearts Valentine’s evening with Martin scores her an impromptu date with a hot waiter—not to mention , who tells Frasier that she calls the guy she’s banging “The Cricket” because “he rubs his hands together really fast during sex.” Get it, girl. [Jenna Scherer]

Futurama, “Love And Rocket” (2002)
Futurama - A wondrous thing happened why not

It comes as no surprise that Bender is the worst boyfriend in the galaxy, robot or otherwise. When Professor Farnsworth tweaks the Planet Express vessel’s A.I. to have a female voice, ’s resident booze-swilling playboy embarks on a whirlwind romance with the ship itself. It’s hard to blame him, considering his girlfriend is voiced by none other than Sigourney Weaver. But Bender’s gonna Bender, and it’s not long before he’s sneaking around behind Planet Express Ship’s back with a series of side pieces (including, sublimely, the disembodied head of Lucy Liu). When he finally breaks things off in the middle of a space battle, his girlfriend goes full HAL and tries to kill herself and the entire crew. The episode saves its true love story for Fry and Leela. The former spends most of it searching Planet Express’ cargo of candy hearts for the perfect message to convey his feelings; but he says it better when he sacrifices his own oxygen supply to save Leela’s life. Fry recovers in time for the pair to hold hands beneath the light of a pink quasar—before Zoidberg inserts himself between them. “And no one could have been happier unless it would have also been Valentine’s Day. What? It was? Hooray!” [Jenna Scherer]

Arrested Development, “Marta Complex” (2004)
“Speech, Speech, Speech!” Marta Realizes She Wants Michael - Arrested Development

With one seemingly uplifting Valentine’s Day speech, Michael Bluth (Jason Bateman) inadvertently destroys three different relationships. Lucille Austero (Liza Minelli) realizes she’s not getting what she needs from Buster (Tony Hale); Lindsay (Portia de Rossi) finally accepts that she’s never really clicked with her husband; and Marta (Patricia Velasquez) realizes she’s in love with the wrong Bluth brother. was always at its best when it fully embraced both the real implications and the wackiness of its punny title, and the dysfunctional relationships that fall apart for relatable reasons but through bizarre circumstances in “Marta Complex” are a perfect example of the show in peak form. [Jen Lennon]

The O.C., “The Heartbreak” (2004)
O.C. - Seth and Summer’s Dance

Seth and Summer losing their virginity to each other on Valentine’s Day? Yeah, writers knew they were appeasing shippers with the classic season-one episode, “The Heartbreak.” Seth and Summer hook up after his sweet declaration of love, yet their first time is anything but memorable. This storyline avoids usual YA tropes and takes a more realistic approach. And that’s not all episode 19 offers: Sandy and Seth having the sex talk, Ryan’s old friend arriving in Newport Beach (much to Marissa’s annoyance), and that “Wonderwall” cover add up to make “The Heartbreak” an excellent holiday-themed hour. [Saloni Gajjar]

The Office, “Valentine’s Day” (2006)
The Office - New York Slice!

You can thank season two episode “Valentine’s Day” for multiple excellent arcs that impacted the show’s legacy in ways big and small. Angela’s bobblehead present to Dwight? Bob Vance proving he’s a delightful gift-giver and Roy proving he sucks? Ryan lamenting after he hooked up with Kelly on February 13? It’s all in the wacky V-Day spirit. Most importantly, Michael and Jan’s romance restarts after she kisses him in the Dunder Mifflin New York office, launching their unhinged multi-season relationship. And for that, “Valentine’s Day” remains iconic. Not to mention, it sets the template for several holiday-themed eps to come. [Saloni Gajjar]

30 Rock, “St. Valentine’s Day” (2009)
Going To The Church on Valentine’s Day In Exchange For Sex | 30 Rock

No poet in history ever described infatuation more eloquently than Kenneth Parcell (Jack McBrayer) when he said, “There’s something about Jennifer that just makes me all carsick inside.” He’s just one of the lovelorn characters in this season three episode, which sees Liz and Jack both struggling through dates with absurdly hot people: the former’s neighbor Drew (Jon Hamm at the height of his fame), and the latter’s girlfriend Elisa (Salma Hayek). Jack begrudgingly pretends to be a devout Catholic for Elisa’s sake, but he’s distracted by visions of splitting a $1,000 dessert at a one-percenter restaurant called, hilariously, Plunder. In classic Liz fashion, she proposes a first date with Drew on the night she realizes, moments too late, is Valentine’s Day. (“Norts!”) What follows is a beautiful disaster that begins with Liz’s breast falling out of her shirt as she slurps a stew she made with “cheddar cheese instead of water” and ends with her sitting alone in a hospital room with Drew’s critically ill mother at the exact moment she dies.Alas, this otherwise sparkling episode gets points off for a subplot involving Kenneth’s date with a new TGS hire whose blindness is portrayed with all the respect of a Mr. Magoo cartoon. Though our favorite page getting Cyrano de Bergerac’d by Tracy is a delightful premise, there’s no escaping the fact that, 15 years down the line, it’s clear how cringe-inducingly ableist this bit was all along. [Jenna Scherer]

Grey’s Anatomy, “Valentine’s Day Massacre” (2010)
GA 6x14 Cristina/Owen/Meredith/Derek

Of course this episode is titled “Valentine’s Day Massacre.” It wouldn’t be Grey’s without a little dying and crying, so the Seattle Grace doctors have to treat patrons of a romantic restaurant when a roof collapses on them. Despite the gloom, there’s plenty of love. The hour sets up Bailey and Ben’s long haul, (blonde) Lexie and Alex’s brief tryst, and establishes Callie and Arizona as a sensible couple (ah, the season six glory days!). And what’s a Grey’s outing without Meredith reminding Derek she hates Valentine’s Day and brunches, but loves sex and surgery? This episode is just a reminder that they really knew what they were doing with the show back then: It’s a glorious mix of tragedy, romance, and blood spilling out of body parts. [Saloni Gajjar]

Parks And Recreation, “Galentine’s Day” (2010)
Galentines Day Reunion - Parks and Recreation

It’s all but become a real-world holiday, so it’s easy to forget that, like Festivus before it, Galentine’s Day was invented whole cloth in a network comedy writers’ room. But this February 13, never forget that the term was coined by one Leslie Knope in this season two episode of . As everyone’s favorite small-town civil servant describes it, Galentine’s Day is a day for “ladies celebrating ladies” with gifts, compliments, and, of course, breakfast foods. “It’s like Lilith Fair, minus the angst … plus frittatas.” But this episode is more about Valentine’s Day proper, as Leslie and her then-boyfriend (Justin Theroux!) embark on a quest to track down her mother’s lost love (John Larroquette!). Meanwhile, Andy plays his first-ever rendition of Mouse Rat’s “Sex Hair,” April breaks up with her gay boyfriends, and Tom finally learns to let go of his fake wife. And of course, Ron is the wisest person in the room: “Basically, Leslie, he’s selfish. And you’re not. And that’s why you don’t like him.” There’s also some stuff with Mark Brendanawicz, but…y’know, who ever remembers Mark Brendanawicz? [Jenna Scherer]

Happy Endings, “The St. Valentine’s Day Maxssacre” (2012)
Happy Endings Season 2 Episode 13 The St. Valentine’s Day Maxssacre

The 2010s’ most chaotic network sitcom sees the series’ quartet of impulsive besties utterly self-sabotaging their respective V-Day plans. Power couple Brad and Jane have pre-arranged the perfect date, but Brad tanks it thanks to the lingering sedatives from a dentist’s appointment earlier that day. (Damon Wayans Jr. deserved an Emmy for Brad’s attempt to romance his wife while dipping his entire forearm in chocolate fondue.) Elsewhere, Dave negs himself straight out of a threesome, and Penny’s plan to delay breaking up with her boyfriend till after V-Day backfires when he calls it off first. As for Alex, she’s less interested in finding love than in St. Valentine himself, a third-century martyr who met his end when “they ripped him tip to taint.” But not everybody bats zero. When the gang reunites in a limo chauffeured by Max (in his latest cash-grab scheme), they join forces to reunite him with the ex-boyfriend (played by an ace James Wolk) he screwed things up with the previous Valentine’s Day. That the episode saves its one sincerely swoony moment for the only gay couple is a testament to how ahead of its time Happy Endings really was. [Jenna Scherer]

New Girl, “Valentine’s Day” (2012)
New Girl: Nick & Jess 1x13 #2 (Nick: You’re not having sex with Schmidt!)

Ladies, who among us hasn’t woken up V-Day with a case of the “dirty twirls”? That’s what Jess is afflicted with, anyway, when she rolls up to her Schmidt asking him to help her score a one-night stand on the big night. (If there’s anyone who knows how to orchestrate a loveless hookup, it’s the guy who has his own Douchebag Jar.) really hits its stride in this season-one episode, helping solidify it as the reigning queen of the 2010s hangout-sitcom era. It’s got everything: Schmidt and Cece’s first hookup, Jess being a complete freak, Winston being a sweetheart to his ex, and Nick trying his best. We’ve also got guest appearances from Lizzy Caplan (as Nick’s workaholic girlfriend), Ryan Kwanten (as Jess’ himbotastic one-night stand), and Clark Duke (as a skeevy intern). “Valentine’s Day” is equal parts character showcase, comedy of errors, and a sweet ode to hopeless romanticism at the dawn of the Tinder age. [Jenna Scherer]

Mad Men, “A Day’s Work” (2014)
Talked About Scene: Episode 702: Mad Men: A Day’s Work

Leave it to Matthew Weiner (and episode writer Carly Wray) to give us a Valentine’s Day episode that’s simultaneously a farce, family drama, and meditation on the nature of relationships in all their forms. And in classic fashion, most of the gang at Sterling Cooper & Partners—whether partnered or not—are married, above all, to their jobs. In one of the series’ funniest running bits, Peggy copes with her angst over her ex-paramour, Ted, by unwittingly stealing a dozen roses that were actually meant for her secretary, Shirley. Over on the West Coast, Pete finds his ambitious equal in real-estate agent Bonnie, and the two essentially agree to a ménage à quatre with their jobs. But the bittersweet heart of the episode is a profoundly lonely Don’s impromptu road trip with his daughter; poor Sally’s eyes have been opened to the truth about her evasive dad, and over a plate of cold fries, the two speak for the first time as equals. Kiernan Shipka’s mumbled delivery of the line “I’m so many people” makes our eyes well up every time. It truly sucks to be a Draper. [Jenna Scherer]

Orange Is The New Black, “You Also Have A Pizza” (2014)
What is love? - Orange is the New Black scene

In its heyday, there was no show better at making viewers simultaneously laugh and weep than Jenji Kohan’s groundbreaking ensemble dramedy. The guffaw-tears are legion in this season-two episode, which, safe to say, is the queerest Valentine’s Day episode of television ever made, between Nicky and Big Boo’s competition to see who can bed the most women in Litchfield and Poussey’s heartbreaking flashbacks to her doomed love affair with a German general’s daughter. It’s also a compelling argument for the idea that the greatest love is platonic, whether it’s Flaca and Maritza baring their souls over a tray of misshapen heart-shaped cookies or Pennsatucky and Healy, brooding over separate heartbreaks, embracing each other in the dark of the prison yard. But the heart of the episode (sorry) is a series of talking heads, sprinkled throughout, in which a rogue’s gallery of inmates answer the question: “What is love to you?” I’ll let the ladies speak for themselves:Suzanne: “All that weird stuff. Whatever’s wrong or bad or hiding in you. Suddenly it’s alright. You don’t feel like such a freak anymore.”Aleida: “24/7, deep-dick, can’t-walk-right fucking.”Sophia: “Pain. Horrible pain. That you want again and again.”Flaca: “It’s like getting into a bath, but the water is like warm chocolate pudding. And the Smiths are playing ‘There Is A Light That Never Goes Out.’ Oh, there’s warm lighting all over, and there’s, like, five dudes massaging you.”Maritza: “And you have a pizza.”Flaca: “She’s right. And you also have a pizza.” [Jenna Scherer]

 
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