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
TV Lists The Gene and Courtney Show
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.
27 Comments
Chuck vs the Masquerade (S4E16)
That’s not even the best part of I Love Lisa.Golden Age Simpsons at its finest.
“I died in 30 days!” made me laugh until I cried. As a refugee of too many elementary school productions that bit could not be more spot-on.
I love the Krusty flashbacks. A Robert Frost and Nation Of Islam joke. This show was untouchable.
Now for my favorite part of the show! Wazzat say? Talk to the audience? Oh GOD, this is always death. MY GOD MAN! I’VE WATERED HER AS FAR AS SHE’LL GO! I CANNA WATER NO MORE!It’s just jam packed. Top 5 all timer, no question.
“We choo-choo-choose the greatest February 14-themed installments to ever grace the small screen, but only since The Simpsons began airing because that’s when TV started.”
Maybe that’s when TV started to have Valentine’s Day episodes? Seriously, I’m sure there were examples from before that, but I’m pretty old and I can’t think of any off the top of my head.
I realize this comment is a year old, but if you’re going to plant a marker, that’s a pretty good episode to choose. Brutal:
It’s a full year later, and you still haven’t posted your examples of great Valentine’s Day episodes from before 1990. I’m sure you’re just taking your time to choose carefully, right?Just for fun I looked up the list on Wiki. There are maybe 20-25 such episodes. There are well over 300 total Valentine’s Day episodes. So, yes, pretty shocking that they picked 15 episodes out of the 92% of them that came out after Simpsons started. But hey, I’m sure by next year you’ll grace us with your hallowed opinion of which of those 25 other episodes they should have included.
I would have accepted any of the Valentine’s episodes of The Middle, but my favorite is probably when Mike volunteers in Brick’s class and Brick has a crush on a classmate.
Holy crap was that a Drivin’ n Cryin’ reference in 2023? Everybody now!
It’s not a VD list unless Xander is being chased by all the women of Sunnydale.
♫♫They did the monster mash
(The monster mash) It was a graveyard smash
(They did the mash) It caught on in a flash
(They did the mash) They did the monster mash♫♫
You played the wrong tape, didn’t you?
Wow, exactly one year to the day.
And the AV Club celebrates a holiday in its traditional way, by saying a fun thing is “cringe-inducingly ableist.” Here’s the bit on 30 Rock, by the way:The joke is on the ridiculous people trying to make the date work, not on the blind woman herself. It’s not discriminatory to note that blind people cannot see — they really can’t.
The first two seasons of Parks and Rec were promising but not great, and “Galentine’s Day” was one of the first where the show really felt like it could reach its potential. I really like the subtle way the show handles the end of the Justin Theroux relationship. He never does anything outright terrible, and many of his character traits (enthusiasm, a tendency to be oblivious to other people’s hesitation) are ones that Leslie herself has. He never stops being, on a superficial level, a good match for Leslie, yet the episode slowly reveals that he’s kind of a jerk. Parks and Rec also finally started to figure out what to do with Ron, who had started the show as a apathetic dick. Ron’s description of Theroux’s character as a “tourist” perfectly encapsulated the doubts about him the show build up slowly all episode.
On Happy Endings, you wrote “quartet” then mentioned at least 5 of the 6 main characters.
Ah yes the infamous week of both Valentine’s Day and Ontario’s statutory“Family Day”. That special time of year where if your homeless without a family or a significant other, you win a kick in the balls!
They should come out with an “Alone Day” for all those alone people.
The Gene & Courtney Show is possibly one of my favorite episodes of TV ever—even though Gene and, especially, Courtney can be extremely grating characters. It even has top-notch B and C plots, with Tina and the Valentines, and Bob/Teddy and the flowers. And the full lyrics to Gene’s song:
If you have good times, and if you have good rhymes,
You may have found your one and only.
But then the one you like-like says, “Take a hike-hike,”
Then suddеnly you’re lonely.
But still be glad, еven if you’re sad.
Take comfort just in knowing
You’ll be okay. It’s Valentine’s Day.
Your heart’s not broken; it’s only growing.
Teddy unintentionally completely blowing Bob’s negotiating at the wholesellers market is one of my favorite Teddy interactions
A happy Anna Howard Shaw Day to us all!
When are we getting a list of the best Leap Day episodes that will only contain that 30 Rock episode
Frasier had one, too!
oooh that’s a good reminder for me to break out my blue and yellow scarf this year.
Let that be a lesson to the rest of you….NUTS
Haven’t seen “The Gene and Courtney Show” in a while, but “V for Valentine-detta” is my personal fave VD episode of “Bob’s”. A pretty good Bob and Gene subplot, a fun caper-like main plot and, most of all, four words: Jillian Bell as Nat.