Whether you plan to celebrate Valentine’s Day with a partner, your Galentine’s gang, or solo, there are plenty of endearing episodes from all types of TV shows to set the mood. Light the candles, grab a box of chocolates, and cuddle up with these 14 sweet Valentine’s Day TV episodes, ranked from least to most romantic. There’s something for cynics and lovebirds alike!
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14. ‘St. Valentine’s Day’ — ‘30 Rock’ (2006 to 2013)
Did someone say Jon Hamm? If you know me, you know I’m a fan of Hamm. While I don’t have “Mad Men” on this list (it did appear on my Thanksgiving TV episodes ranking), a Hamm storyline is still worth including here due to his prominent role in “30 Rock” Season 3, Episode 11. Thank you, Liz Lemon (Tina Fey)!
In one of the most awkward and action-packed Valentine’s Day dates (and first dates) in the history of television, Liz and her neighbor-turned-date Dr. Baird (Hamm) experience more mayhem and embarrassment in the span of one night than many couples do in years. Bathroom distress, death, and scandal are just a few of the highlights. Meanwhile, Jack (Alec Baldwin) endures an uncomfortably hilarious outing to church with his girlfriend Elisa (Salma Hayek), while Kenneth (Jack McBrayer) tries his luck with a blind woman.
13. ‘If Boys Were Girls’ — ‘Malcolm in the Middle’ (2000 to 2006)
“Malcolm in the Middle” has been a recent TV staple in my household, with both of my kids miraculously agreeing to watch it together. As with most episodes of the series, “If Boys Were Girls” features the dysfunctional Wilkerson family enduring its fair share of boy-driven antics, this time mostly in a mall. Matriarch Lois (Jane Kaczmarek) is ultimately left wishing the baby she just found out she’s expecting is a girl.
Morning sickness and general havoc contribute to this episode’s low romance ranking — a Valentine’s Day spent vomiting is never a good one. At least Lois’s husband, Hal (Bryan Cranston), tries his best to find her a suitable Valentine’s Day gift, and his valiant efforts don’t go unnoticed.
12. ‘Valentine’s Day’ — ‘The Office’ (2005 to 2013)
My heart goes out to Pam Beesley (Jenna Fischer) anytime I catch the first Valentine’s Day episode of “The Office.” How many Valentine’s bouquet deliveries can one woman accept without being the intended recipient? If you skew more toward the bitter end of the spectrum when it comes to this overly corporate holiday, this episode is for you.
While Phyllis (Phyllis Smith), Michael (Steve Carell), Dwight (Rainn Wilson), and Angela (Angela Kinsey) each have some romance-adjacent moments, there’s a lot more torment than there is love among the office staffers. Can we fast-forward to the Jim (John Krasinski) and Pam era, please?
11. ‘Valentine’s Day’ — ‘Abbott Elementary’ (2021 to Present)
ABC’s acclaimed series “Abbott Elementary” is well-loved by fans and critics alike. The Season 2 Valentine’s Day episode isn’t packed with romance, but Janine (Quinta Brunson) does finally become aware that Gregory (Tyler James Williams) likes her amid the show's ongoing “Will they or won’t they?” storyline, and we think that’s cute.
After Janine and Gregory have awkward gift exchanges with their current love interests, we’re left hoping they’ll properly get together in Season 3. Despite a “whoops” kiss moment last season, the two are still platonic (for now).
The third season premieres on ABC this month. You can also catch up with your favorite teaching staff on Hulu.
10. ‘Stupid Things in the Name of Sex’ — ‘The Resident’ (2018 to 2023)
I enjoyed the first few seasons of “The Resident” but gradually lost interest as some of my favorite characters departed. That said, the Season 2 Valentine’s Day-themed episode of the medical drama was during the show’s peak and warrants a low-to-mid-range romance rating, thanks in part to Nurse Jessica (Jessica Miesel) and her adorable heart scrubs.
In the episode, the series’ most beloved couple, Conrad (Matt Czuchry) and Nic (Emily VanCamp), aren’t able to make their fancy dinner reservation, but they do manage to find simple moments of love and bliss. Many of Chastain Park Memorial Hospital’s other couples enjoy love infusions, including when Jessica and Irving (Tasso Feldman) make their relationship public.
Meanwhile, the latter’s speculation about whether the ER will see more suicide attempts or proposals gone wrong on the holiday hits the right notes for Valentine’s Day cynics. Speaking of proposals, I won’t spoil the “who,” but there is in fact a marriage proposal in the episode!
9. ‘My Funky Valentine’ — ‘Modern Family’ (2009 to 2020)
There’s no love lost in “My Funky Valentine.” Each of the “Modern Family” couples attempts to be on top of their respective love games as they celebrate the holiday, all to varying degrees of success. The big highlight is the story centering on one of my all-time favorite TV couples, Phil (Ty Burrell) and Claire (Julie Bowen) Dunphy.
The pinnacle comes as Claire’s trench coat (under which she has no clothing) gets stuck in an escalator. As luck would have it, while Claire is unable to move from the escalator, the couple runs into every respectable person in their sphere after their sexy role-playing bar date goes awry. It’s almost a romantic win.
8. ‘I Love Lisa’ — ‘The Simpsons’ (1989 to Present)
It’s no surprise the longest-running animated show in television history has eight episodes centering around Valentine’s Day. Season 4’s “I Love Lisa” is a standout classic packed with quintessential “Simpsons” humor, one-liners, and some animated amore to boot. Lisa (Yeardley Smith) sends an “I choo-choo-choose you” card to Ralph (Nancy Cartwright), which is meant to be platonic but isn’t received that way. It remains one of the most relatable Valentine’s Day card mishaps ever.
Marge (Julie Kavner) comes through as the levelheaded mom, giving Lisa solid advice for dealing with Ralph’s unwanted crush. In comparison, Ralph’s dad, Chief Wiggum (Hank Azaria), imparts some less-than-desirable advice to his son. Friendship wins in the end.
Get smitten with “The Simpsons” on Disney Plus, and explore other ways to watch the series online or over the air without cable.
7. ‘Doug Plays Cupid’ — 'Doug’ (1991 to 1999)
I love nostalgic TV. Even as an adult, I find there’s nothing like reminiscing over old cartoon favorites from childhood. Here, Doug (Billy West) spends another episode swooning over the ever-unavailable Patty Mayonnaise (Constance Shulman), going over the top as usual by being his kind and concerned — albeit desperate — self. Unfortunately for Doug, he’s unknowingly in over his head in the weird spot between the “childhood sweethearts” and the “never going to happen” TV love tropes. While it’s not a proper Valentine’s Day-themed episode, there’s enough young romance to still earn a spot on this list.
Case in point: School bully Roger (Billy West) shows his soft side as he pursues his love interest, Beebe (Alice Playten), and eventually employs Doug to play Cupid and help him become a gentleman in the hope that Beebe will go out with him. In only 22 minutes, everything works out as it’s meant to.
6. ‘Valentine’s Day’ — ‘The Golden Girls’ (1985 to 1992)
Thank you for being a friend, and thank you to “The Golden Girls” for giving us this memorable Valentine’s Day episode. The iconic roommates appear to be stood up by their respective dates, so the group takes the opportunity to gather around their kitchen table and relive moments of glory from Valentine’s Days past.
As you’d expect, their lifetime’s worth of memories and antics make for a fun walk down memory lane. From a Valentine’s massacre of sorts to indulging in a nudist retreat, the funny flashbacks alone are worth tuning in for. But the episode comes to a sweet conclusion when Sophia (Estelle Getty) gets her secret boyfriend Julio Iglesias (the real-life singer!) to sneak in the back door for a furtive rendezvous after the rest of the ladies end up hitting the town with their dates after all.
5. ‘Valentine’s Day Massacre’ — ‘Brothers & Sisters’ (2006 to 2011)
Before “This Is Us,” there was “Brothers & Sisters” and “Parenthood.” This trio of shows is filled with emotional family dynamics and romantic love. In “Brothers & Sisters,” the Walker siblings (Rachel Griffiths, Calista Flockhart, Balthazar Getty, Matthew Rhys, and Dave Annable) are the most romantic in Season 1, Episode 14’s “Valentine’s Day Massacre” (yes, despite that off-putting title).
The first five minutes of the episode pick up the day after Valentine’s Day, with a compellingly chaotic phone call among family members as the group avidly gossips about their escapades the night before. And there’s a lot to gossip about. Kitty Walker (Flockhart) and Senator Robert McCallister (Rob Lowe) have their first physical encounter, a surprise turn of events to everybody except Kitty. The “earthquake” joke the morning after couldn’t have been cuter, even alongside Kitty’s revelation that the senator has bigger political aspirations in mind.
4. ‘Mary Anne and the Great Romance’ — ‘The Baby-Sitters Club’ (2020 to 2021)
Despite Netflix’s cancellation of “The Baby-Sitters Club,” the show’s two-season run was cute while it lasted. Fans of the book-turned-TV series have rooted for Mary Anne (Malia Baker) and Dawn’s (Kyndra Sanchez) dating parents to wed for some time, but this episode keeps us waiting for that happy ending.
What happens instead is a heartwarming look at innocent teenage love with themes of friendship and self-love as the cherries on top. In the main storyline, Mary Anne and Logan (Rian McCririck) explore their boyfriend-girlfriend status with a fancy formal date that ends up as a double date with Mary Anne’s dad, Richard (Marc Evan Jackson). The father-daughter duo has quite a few loving moments in this episode, which shows they’ve come a long way in their own relationship journey.
3. ‘Baby Makes Five’ — ‘Beverly Hills, 90210’ (1990 to 2000)
While “Beverly Hills, 90210” features eight Valentine’s Day episodes across its 10-season run, I’m most enamored with Season 2’s “Baby Makes Five.” The heavy Brenda (Shannen Doherty) and Dylan (Luke Perry) storyline is not only right up my alley as a “Team Brenda” devotee, but the social impact of the plot is also heartwarming.
Dylan opts to bring Brenda on a nonconventional Valentine’s date to donate blood. As he explains, he was in a car accident as a child on Feb. 14, requiring a blood transfusion. He promised himself he’d donate blood when he was old enough, and now he is. For such a “bad boy,” he was actually pretty good when he tried.
During a conversation in 2022 with late “Beverly Hills, 90210” executive producer Jessica Klein, who cowrote the episode, I learned this episode led to an increase in Red Cross blood donations after it aired. Now that’s impact. This episode also ranks highly on my list because it ups the Valentine’s Day ante by combining a pregnancy reveal (hence the episode’s title) with a marriage proposal.
Fall in love with “Beverly Hills, 90210” all over again on Paramount Plus, or watch its dedicated PlutoTV channel.
2. ‘You Also Have a Pizza’ — ‘Orange Is the New Black’ (2013 to 2019)
Romance is the name of the game in the “Orange is the New Black” episode, “You Also Have a Pizza,” along with a heavy dose of innuendo and emotion, and a Valentine’s Day party to boot. This love-themed Season 2 installment opens with some of the Litchfield ladies sharing what love means to them.
Notably, love runs strong among the inmates despite the dark backdrop of a penitentiary. The episode leans into a multitude of romance tropes, from forbidden love to separated lovers. Highlights for me include the flashbacks of a pre-prison Poussey (Samira Wiley), kicking off with the romantic track “Hey There Delilah” by the Plain White T’s to set the mood.
We also learn a fun fact about a television legend. Piper (Taylor Schilling) points out to her boyfriend that Valentine’s Day is also “The Brady Bunch” matriarch Florence Henderson’s birthday. I looked it up and it’s true — Feb. 14 is, in fact, Henderson’s birthday.
Lock up your Valentine's date night with HBO’s “Orange is the New Black” on Netflix.
1. ‘First Date’ — ‘That ‘70s Show’ (1998 to 2006)
The start of Eric (Topher Grace) and Donna’s (Laura Prepon) official relationship in the “That ‘70s Show” episode “First Date” ranks highest on my romance scale. In Season 1, when the show was at its best, this episode unknowingly set up what we saw in the series’ recent revival-slash-sequel, “That ‘90s Show.” Eric and Donna end up married!
But first, all those years ago, their first date involved underage drinking and a love triangle with their friend, Hyde (Danny Masterson). As Fez (Wilmer Valderrama) astutely points out in the episode, competition between two friends like Eric and Hyde is one of the oldest stories in history; it’s also another common Valentine’s Day TV trope. Fortunately, it’s Eric who wins Donna’s affections, and despite the slight involvement of vomit, my heart soars seeing the beginnings of these TV soul mates.
Additional points are awarded to Kitty (Debra Jo Rupp) and Red (Kurtwood Smith) for keeping their romance fresh. Plus, I just love that the actors who play the on-screen couple, Jackie (Mila Kunis) and Kelso (Ashton Kutcher), are now married off-screen. It doesn’t get much sweeter than that.