17 Best Valentine’s Day TV Episodes Ever

The next month and a half leading up to Valentine’s Day is all about ~love~. You’re going to see chocolates, flowers, and teddy bears in every corner of every store until February 14th. And then you can celebrate February 15th, aka National Valentine’s-Day-Candy-is-Half-Off day. But until then, we’re stuck with the pink and red color palette everywhere. And what better way to celebrate the season than with some truly lovely episodes of TV?

Television has a way of making love stories into the most unrealistic thing on the planet. But we love it. Give me a grand romantic gesture or a totally scripted speech any day! Sometimes it’s fun to live vicariously through the love lives we’re definitely never going to have. Here’s to feeling all the emotions! Check out some of the best Valentine’s Day-themed TV episodes to binge over the next few weeks!

17. How I Met Your Mother, “Desperation Day”

This is a classic Barney (Neil Patrick Harris) episode, as he proves how much of a dog he really is the day before Valentine’s Day. He dubs February 13th as “Desperation Day” and sets out to find a girl so desperate for love and affection before V-day that she’ll basically be begging to sleep with him. It’s pretty skeevy, to be honest. Maybe let’s not paint women as desperate heathens looking for love on TV anymore? Good thing Neil Patrick Harris is just so damn charming that we know his motives must be at least a little admirable.

16. Boy Meets World, “First Girlfriends Club”

Let’s be honest — Shawn Hunter (Rider Strong) was a bit of a player. How could he not be with that perfect, flippable hair?! But when he met Angela (Trina McGee) all of that changed and he turned into a one-woman kind of guy. Well, his exes had a few things to say about that. On Valentine’s Day, they hold him captive, so he can’t break Angela’s heart the same way he brother theirs. It’s sad to see what his high school antics did to these girls, but even sadder than that is how they can’t accept that he’s changed. Eventually, Angela shows up and saves him, and everyone realizes Shawn’s good intentions in that particular relationship. It’s a great ode to how sometimes people really do change, especially when they find a love worth changing for.

15. Glee, “Silly Love Songs”

Sometimes the way to someone else’s heart is through music and Glee totally has that covered. The episode gets its name from the Warblers cover of “Silly Love Songs” by Paul McCartney & Wings. This whole episode is basically about bad timing. Rachel (Lea Michele) and Finn (Cory Monteith) can’t get it together while Finn’s off trying to get back with Quinn (Diana Agron) who’s in a relationship with another guy. Drama! No one ends up happy or with who they want to be their Valentine, but that makes it feel just a little more like real life cause let’s face it — Valentine’s Day sucks — especially in high school.

14. Gossip Girl, “Crazy Cupid Love”

Hello Upper East Siders, time for a cray Valentine’s Day. This is the episode where Blair (Leighton Meester) and Dan (Penn Badgely) finally kiss after growing unexpectedly close. Some hate the couple, but kudos to the show for adding a whole other layer of WTF to everything with that relationship. While Blair denies feelings for him for a little bit longer after this, the two eventually take a shot at it, and it’s surprisingly sweet. This episode is also yet another reminder that it’s literally impossible for Dan to be Gossip Girl her(him)self, but whatever — we’ll let it slide (do we have a choice?).

13. Orange is the New Black, “You Also Have Pizza”

It’s Valentine’s Day in prison on this episode of Orange is the New Black. The inmates all give their descriptions of what love is, with Marisol ending her definition with “you also have pizza” because — duh — being in love and having pizza are both amazing feelings. The episode is full of couples trying to get together, some breaking up, and some wrestling with some unrequited feelings. (Relatable.)
The true heart of the episode comes from Poussey’s (Samira Wiley) flashbacks where we learn she was in love with a female friend until that person’s father ends up finding out they’re together and breaking them apart, calling their affair a “problem” that needs to be fixed. It’s heartbreaking and adds a whole new layer to the characters’ feelings on Valentine’s Day in the present.

12. New Girl, “Valentine’s Day”

Jess (Zooey Deschanel) is preparing for her first Valentine’s Day alone and looking for a one night stand to ease her loneliness. Schmidt (Max Greenfield) agrees to be her wingman since this is kind of his forte. As you may have expected, things don’t go as planned and Jess ends up alone anyways. But this has positive consequences: Jess learns that it’s always better to be alone than to be with the wrong person. And that’s a lesson any single girl can use on V-day.

11. Friends, “The One With the Candy Hearts”

Oh. My. God, it’s a Valentine’s Day Friends episode. Janice (Maggie Wheeler) stumbles back into Chandler’s (Matthew Perry) life just in time for the holiday and the two end up, briefly, rekindling their relationship. Although she insinuates it won’t last long, Janice ultimately gives her on-again-off-again boo some candy hearts that have “Chan and Jan Forever” printed on them. Typical Janice.

Elsewhere, Ross (David Schwimmer) finds himself on his first date in nine-years (post-divorce), but still ends up at a table with his ex and her new girlfriend when they both choose the same restaurant. In a touching moment, they both lament the end of their love and the better things on the horizon. The most relatable part of the episode? The girls — all single, burning mementos of past relationships. Sure, it ends with a fire (which means hot firemen!), but it’s the thought that counts.

10. Happy Endings, “The St. Valentine’s Day Maxssacre”

Oh, Happy Endings, the gem of a show that left us too soon. This Valentine’s Day episode has all the things that made the show great: Penny (Casey Wilson) being crazy, Jane (Eliza Coupe) being neurotic, and Alex (Elisha Cuthbert) being mistaken for a hooker. All that good stuff! We watch as Penny tries to postpone breaking up with her latest boo until after the holiday — but her tactic has Dave (Zachary Knighton) starting to think his new girlfriend is doing the same to him. No one wants to be alone on Valentine’s Day, even if they know they aren’t with “the one.” The best part of the episode is Brad’s (Damon Wayans Jr.) trip to the dentist and the ensuing silliness.

9. Mad Men, “A Day’s Work”

This episode is great for the rare glimpse at Don (Jon Hamm) bonding with his children. His day with Sally (Kiernan Shipka), the one child who can see right through him, shows just how similar to one another the two are. Their time together also clearly displays that Valentine’s Day isn’t just for couples — it’s for the love between family, too. And Sally telling Don she loves him at the end of the episode is as heartwarming as it gets.

8. Parks and Recreation, “Operation Ann”

Parks and Recreation knows how to do a great holiday episode and Valentine’s Day is no different. This installment has Leslie (Amy Poehler) trying to find her BFF, Ann (Rashida Jones) a date, but her options are kind of scarce. Everything is culminating at the Valentine’s Day dance, DJ-ed by a hella-depressed Chris (Rob Lowe), who’s playing the most dreary music you can imagine. At least Leslie and Ben (Adam Scott) are happy, as Ben tries to complete the crazy complex and very loving scavenger hunt Leslie laid out for him for the big romantic holiday.

7. The Vampire Diaries, “Total Eclipse of the Heart”

On The Vampire Diaries you can never expect any holiday to go to plan. In an attempt to be normal college students despite being undead supernatural creatures, the girls decide to go to the “Bitter Ball” on V-Day to deal with being single on the holiday. While Valentine’s Day is most often seen as a day for romantic love — this ep really proves that maybe it’s actually better to celebrate the holiday as a day for the realest type of love: friendship.
Elena (Nina Dobrev) is not actually Elena this entire episode, though, she’s Katherine and nobody notices. Her BFFs, her exes, her family — no one! That is until her childhood friend (also ex-boyfriend) and all-around gent, Matt (Zach Roerig) finally figures it out. Luckily Elena has a friend like Matt on Valentine’s Day; someone who truly knows her.

6. The Office, “PDA”

Michael (Steve Carrell) and Holly’s (Amy Ryan) PDA is out of control on Valentine’s Day and the entire office is over it. Because of this, the office has a meeting about PDA in the workplace, attended by Jim (John Krasinski) and Pam (Jenna Fischer) who had a bit too much Valentine’s Day champagne at lunch and are now a bit tipsy at work. Their lowered inhibitions lead them into some PDA of their own in the office, i.e., doing it in the closet at work. While basically everyone this episode probably should’ve been fired, it’s sweet to see how ~in love~ these coworker couples are.

5. Modern Family, “My Funky Valentine”

It’s all about switching things up on this Modern Family Valentine’s Day episode. Instead of taking Claire (Julie Bowen) to the same restaurant he has for the last 17 years, Phil (Ty Burrell) decides to switch things up. The two go to a hotel for the night and engage in a bit of role play. Naturally, it goes horribly awry because this is a sitcom after all, but it shows how important it is to put a little effort into your relationships once in a while — even ones you’ve grown used to. You may spill oil everywhere or get your coat caught on an escalator… when it’s the only thing you’re wearing… and in front of one of your parents… but at least you’re putting effort in!

4. Buffy the Vampire Slayer, “Bewitched, Bothered, and Bewildered”

On Buffy, you know no love story is going to be typical. When Xander (Nicholas Brendon) is broken up with by Cordelia on the holiday of love, he blackmails a classmate/witch into helping him get her back with a love spell. Unfortunately, love spells are *the worst* and it goes completely wrong — making every other woman but his ex falls in love with him. Next thing you know, Xander is running from friends, foes, teachers, and parents (including Buffy’s mom) as he tries to rebuff their advances. Eventually, the spell is reversed, the embarrassment is forever, and it turns out Cordy loved him all along.

3. Friends, “The One With the Birthing Video”

What’s more romantic than watching someone give birth? Oh, everything in the world? Chandler accidentally watches a birthing video thinking it’s porn from Monica (Courtney Cox) — and the two proceed to lose all hopes of romance for the rest of the night. Sure, it’s ~the miracle of life~, but ew! Not on Valentine’s Day! Ross isn’t having the best V-day either, as he lies to his girlfriend about Rachel (Jennifer Aniston) living with him. Probably not the best move, dude. It’s also probably why this is their first, last and only Valentine’s Day spent together.

2. 30 Rock, “Anna Howard Shaw Day”

One of the best 30 Rock episodes of all time happens to be a Valentine’s Day episode. A single Liz (Tina Fey) schedules dental surgery for Valentine’s Day hoping it will allow her to just bypass the holiday. But there’s one big problem — she has no one to pick her up. This leads to a drugged-out Liz in the waiting room hoping her anesthesia will wear off and hallucinating all of her ex-boyfriends (and Bon Jovi!) being there to see her. A lonely Jenna (Jane Krakowski) also tries alternative means to feel better on the holiday — i.e., harassing her stalker about why he isn’t stalking her anymore. Don’t ever change, Jenna, we feel your pain.

1. Parks and Recreation, “Galentine’s Day”

This episode brought us the joy that is Galentine’s Day. and our lives have truly never been the same since. February 13th is a day for celebrating the ladies in your life, free from partners, SOs, baes, and spouses. Leslie creates this holiday to shower her friends with love and gifts (and waffles) that only Leslie Knope could come up with. It’s the ultimate way to show what Valentine’s Day is really about ‐ love, in all its many forms. Whether you’re single or in a relationship, you can celebrate Galentine’s Day every year with your BFFs and remember just how lucky you are to have your gals.

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