In theory, Valentine's Day is hands-down the most enjoyable holiday. You get to bask in all the festive trappings—shiny chocolate boxes, as much red wine as you can stomach, a tender filet mignon by candlelight—without the meal prep and headaches (looking at you, Thanksgiving). But if the best Valentine's Day TV episodes teach us anything, it's that romance is a lot messier than "table for two."
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Just ask Don Draper. Even TV's consummate womanizer, so seductively played by Jon Hamm across seven seasons of "Mad Men," has been off his game on V-Day. Then there's the cringe-worthy flirtationships that populate "The Office," holding up a mirror to every red-faced interaction you've ever had with that special someone.
Below, we spotlight 15 of the best Valentine's Day TV episodes from shows new and old now available on streaming. Tapped out on all the classic rom-coms? Our picks include funny moments from your favorite sitcoms: Liz Lemon literally renamed the holiday in private protest on "30 Rock," and Chandler's V-Day was forever ruined by a surprise birthing video on "Friends."
Looking for a period romance, or an intimate drama with soaring emotion? We also pose a few tear-jerkers for your consideration, including a devastating episode of "This Is Us" and a mournful, feature-length installment of "Downton Abbey."
Whatever your pleasure this cupid's day, the following memorable moments have stood the test of time. Here are the best Valentine's Day TV episodes to stream right now.
'The Office' - "Blood Drive"
NBCU
Season 5, Episode 16 offers a perfect mix of classic "Office" cringe and Valentine's Day whimsy. Micheal meets his dreamboat lover girl at a blood drive, then holds a lonely hearts party at the office in the hopes that she'll show up.
'Mad Men' - "For Those Who Think Young"
AMC
The Season 2 premiere of "Mad Men" is the show's smokey 1960s allure turned up to 11. Don takes Betty to the Savoy on Valentine's Day and has an embarrassing moment in the bedroom afterwards.
'Downton Abbey' - "Episode One"
Nick Briggs/ITV
Looking for a tear-jerker with gorgeous period touches? The Season 4 premiere of "Downton Abbey" puts a somber spin on the classic V-day love plot as Mary, six months after Matthew's death, remains in mourning. At 1 hour 30 minutes, it's the first feature-length episode of the series — and one of the best.
'Friends' - "The One With the Birthing Video"
NBCU
Phoebe lands one of her greatest zingers in Season 8, Episode 15 of "Friends." She leaves a graphic birthing video for Rachel, but it ends up in front of an unsuspecting Chandler.
'Parks and Recreation' - "Operation Ann"
NBCU
Leslie's Galentine's Day parties on "Parks and Rec" always kill (Season 2; Season 6). But we chose Season 4's "Operation Ann" for its wacky commitment to the game of love. Leslie tries to set Ann up with someone at the senior citizen's dance, and Ron and Andy complete the world's toughest scavenger hunt.
'New Girl' - "Valentine's Day"
Greg Gayne/FOX
Of course "New Girl" excels at showing all the messiest sides of romance. In Season 1, Episode 13, Nick and Julia's first V-Day together is foiled, and Jess attempts her first one-night stand.
'The Office' - "PDA"
NBCU
Michael and Holly can't keep their hands off each other. Jim and Pam drunkenly scour the office for the ideal love nest. Erin and Andy are thrust together in a Valentine's Day treasure hunt. Season 7, Episode 15 is another pitch-perfect "Office" romance plot.
'Gossip Girl' - "Crazy, Cupid, Love"
The CW
It's Valentine's Day on the Upper East Side in Season 5, Episode 15, and Blair can't resist playing cupid for someone she loves. Meanwhile, Georgina crashes Nate's party and gets ~something~ off her chest.
'Modern Family' - "My Funky Valentine"
ABC
Season 1, Episode 15 is "Modern Family" at its early best. Claire goes commando under a trench coat for a role-playing fantasy with Phil, which goes awry when she comes into contact with an escalator. Elsewhere, the late-great David Brenner roasts Jay and Gloria's age gap in his stand-up set.
'Gilmore Girls' - "A Vineyard Valentine"
Warner Bros.
Luke and Lorelai + Rory and Logan + Martha's Vineyard = an awkward Valentine's Day for the ages. Season 6, Episode 15. Get on it.
'The Nanny' - "Love Is a Many Blundered Thing" (1996)
CBS
Season 3, Episode 19 was a turning point for Fran and Maxwell's flirtationship. And in terms of physical comedy, you really can't do better than Fran Drescher in this wacky, adorable V-Day special: Thinking a mystery Valentine's card was from Mr. Sheffield, Fran puts up an embarrassing billboard in Times Square — then tries furiously to take it down.
'And Just Like That...' - "February 14th"
HBO
"And Just Like That..." is the definition of a mixed bag, but Carrie's slightly tortured musings about her dinner date with Aidan in Season 2, Episode 7 is worthy of old school SATC fans' attention.
'Grey's Anatomy' - "Valentine's Day Massacre"
ABC
Here's a throwback for you: A married Derek and Meredith, along with the rest of the team at Seattle Grace, race to treat dozens of injured lovers after the roof collapses at a restaurant on Valentine's Day.
'This Is Us' - "Jack Pearson's Son"
NBCU
No better way to join the broken hearts club than by watching Season 1, Episode 15 of "This Is Us." Randall has a breakdown, and Jack and Rebecca's Valentine's Day flashback is the beginning of the end.
'30 Rock' - "Anna Howard Shaw Day"
NBCU
Watch Liz Lemon unravel as she battles her longtime hatred of Valentine's Day—which she's personally renamed to Anna Howard Shaw Day, after the women's rights icon—in Season 4, Episode 13. In an effort not to spend the holiday alone, she schedules a dental surgery — then can't find anyone to give her a ride.
