Pop culture obsessives writing for the pop culture obsessed.
Screenshot: Mary Tyler Moore show, Parks And Recreation, Photo: Black Mirror (Netflix), Graphic: Natalie Peeples

Competition is in the air, thanks to March Madness, but the return of the dating series has us thinking about perfect pairs instead of an elite eight. Two new comedies, Hulu’s Shrill and Starz’s Now Apocalypse, capture the steep highs and lows of modern dating for folks of all sizes and orientations. Elsewhere, Netflix has Dating Around, a kind of successor to MTV’s Next, as well as the upcoming, only slightly darker French-language series Osmosis, which shows just how painful finding your soul mate can be even with the help of an app. But even though we can summon a date as readily as a pizza these days, it doesn’t mean these apps always deliver; more often than not, what would-be lovers need is a little human guidance, which is why we’re taking a look back at some of our favorite TV fix-ups and letdowns. As our own sweet sixteen proves, user error can be as big a problem as cold, unfeeling A.I.—sometimes it even reveals a lack of compatibility—but at least it’s not likely to lead to Skynet.


1. Parks And Recreation, “The Set Up” (season two, episode 13)

Katie Dippold’s (The Heat) script for “The Set Up” delves into accessibility on the professional and romantic fronts. While Ron fends off surprise visitors as the result of a new government initiative, Leslie Knope sets out to date in earnest again. Keen to be fixed up, she looks to her best friend Ann, who is currently dating her former flame (if Mark could be called that). Though a great option is staring them both in the face—Justin Theroux as as a handsome lawyer also named Justin—Ann’s doubts about Mark lead her to “save” Justin for herself and set Leslie up with an MRI technician named Chris (guest star Will Arnett). Despite his job, Chris is incredibly shallow and whiny, openly complaining about Leslie’s “flaws,” like being an Indiana alum, while expressing admiration for her uterus, which, in a bit of foreshadowing, he tells her has room for triplets. Thanks to hindsight, we know that Ben Wyatt (Adam Scott) was waiting to show up at the end of the season, which makes Leslie’s string of romantic disappointments a little more bearable. [Danette Chavez]


2. Frasier, “The Matchmaker” (season two, episode three)

Seattle’s most uncertain recipient of tossed salad and scrambled eggs attempts to play Cupid in this second-season installment of the sitcom, and the ensuing situations plays to many of the show’s stage-farce strengths. After Frasier’s live-in housekeeper/physical therapist to his father, Daphne, complains about her lack of romantic prospects, the radio psychiatrist decides to find her a man. Unfortunately, while describing the kind of man he’s looking for, Frasier is overheard by the station’s new manager, Tom, who is gay and assumes from the conversation that Frasier is as well. Thus, Frasier’s invitation for Tom to come for dinner turns into a night of comical misunderstandings, in which Frasier, his father, and brother Niles are all at some point mistaken as being gay. It may sound like a groaner of a premise, but the episode actually won a GLAAD Media award for its handling of homosexuality in a comedic but thoughtful manner. [Alex McLevy]


3. Black Mirror, “Hang The DJ” (season four, episode four)

The rare bright (as in optimistic) spot in a season of Black Mirror, “Hang The DJ” shows its central characters defying a matchmaking algorithm to make up their minds for themselves. Amy and Frank are two twentysomethings who, like everyone around them in this Charlie Brooker-written future, use an app/machine called “Coach” to help them navigate dating life. They click on their first date, so naturally, they check the service to see how long they’re going to be together. The answer: 12 hours. They make the most of their night together, then spend years apart in unsatisfying trysts and relationships before getting a second chance. Frank’s insecurity leads to another split, but when Amy is faced with a marriage to someone she’s never met before, she reunites with him one last time. It dawns on her that their trials and tribulations are the actual compatibility test, and she asks Frank to take a leap of faith. Their decision to listen to their own instincts instead of some artificial intelligence breaks the cycle, and leads to a lovely scene with other permutations of their relationship. That revelation turns out to be its own simulation, but the moment Amy and Frank’s eyes meet for the real first time is pure organic connection. [Danette Chavez]


4. Crazy Ex-Girlfriend, “I’m Going On A Date With Josh’s Friend!” (season one, episode four)

When Rebecca’s lifelong rival marries a hedge fund manager and snags the promotion she herself turned down, Rebecca spirals. Heather’s solution: find someone to “pound the bad feelings”out of her. 20 minutes later, Rebecca’s with Jason from Tinder, whose carpal tunnel balls make him the perfect bad decision, one depicted via a “Partition” parody that is far more concerned with the anxieties associated with having sex with a rando (being murdered, contracting an STD, him harvesting her kidney) than its allure. The “date” falls apart when a butter commercial shames Rebecca into making “healthier choices.” Doing Jason from Tinder is not one of them, and Rebecca proceeds to make similarly impulsive decisions (Buddhism, veganism) to counteract it . The healthiest decision she makes is agreeing to go out with Greg, but Rebecca’s impulsivity comes back into play when their date goes surprisingly well. Facing the frightening possibility of a healthy, mature relationship, Rebecca stress-eats a meaty burrito and ditches Greg for the Vegan Guacamole Man. In terms of making healthy choices, Rebecca’s got a long way to go. [Maggie Donahue]


5. Brooklyn Nine-Nine, “DFW” (season five, episode 17)

As LaToya Ferguson noted in her review last year, Rosa and Gina are the Nine-Nine’s “too cool for school” kids, which is just one of the reasons they’re such a compelling duo even when their screen time together is limited. But their chemistry is what makes the matchmaking B-plot of “DFW” an episode highlight, along with Jake leading a suspect lineup in a Backstreet Boys singalong and Terry’s resulting injuries after he throws himself into yoga with typical Terry zeal. We learn just how well Gina knows her co-worker, presenting her with a bevy of options in a slideshow to throw her off the scent of the real fix-up. Gina talking up her female friends to Rosa while using a soundboard packed with recordings of Holt saying things like “sexual” and “get some” is one of the most hilarious and incongruous things about the episode, and almost renders the successful match toward the end irrelevant. [Danette Chavez]


6. Friends, “The One With The Pediatrician” and Paul Rudd (season nine, episode three)

As you might expect from a group of Friends, the Central Perk pals regularly fixed each other up, though with very little success. There was the one where Chandler sets Rachel up with one of his co-workers, only to debate the meaning of the word “casual”; Rachel returns the favor at one point by hooking Chandler up with her boss. But the most memorable fix-up scenario comes fairly late in the show’s run: In “The One With The Pediatrician,” Joey and Phoebe agree to find dates for each other, which Joey of course forgets to do. The night of the double date, he runs to Central Perk, where he yells out the name “Mike”—which is the name he gave Phoebe on the fly—and bumps into Paul Rudd. The dinner is a fiasco, as Joey turns out to be terrible at improv and, despite his date being beyond suitable for him, he’s incapable of remembering her name. But Phoebe and Mike still manage to hit it off, which is the start of a charming and enduring relationship. [Danette Chavez]


7. Gilmore Girls, “Double Date” season one, episode 12

Beware the blind date! As often happened on Amy Sherman-Palladino’s excellent dramedy, mother and daughter found themselves in similar predicaments, this time involving romance. Rory is tasked by her best friend Lane with setting her up with Todd, a friend of Rory’s boyfriend Dean, so the four embark on a double date in which Lane quickly realizes Todd is a bit too monosyllabic to be a good match. Meanwhile, Lorelai gets roped into a double date with Suki and her produce supplier Jackson, getting paired up with Jackson’s visiting cousin Rune, who not only immediately expresses his distaste for Lorelai, but is easily one of the most boorish and obnoxious men with whom she’s ever been forced to endure a blind date. Thankfully, by episode’s end, both Todd and Rune have been cast aside (“Bye, Loon!” Lorelai merrily mispronounces as he scurries off), and the Gilmores get back to the normal state of affairs in the early years—Rory with a boyfriend and Lorelai being surreptitiously crushed on by Luke. [Alex McLevy]


8. Living Single, “Wake Up To The Breakup” (season three, episode 17)

Screenshot: Living Single

For much of Living Single’s five-season run, Kyle and Maxine’s relationship wavered between love and hate. They were ideal sparring partners, each possessing a cutting wit, but we didn’t realize how great a sort-of couple they were until “Wake Up To The Breakup.” By season three, Max and Kyle had already hooked up a few times, but when Kyle tries to deepen the relationship, Max pushes him to date a lovely cable tech to prove how little she cares about whatever their relationship status is. But she is jealous or at least uncertain of how to deal with Kyle’s growing feelings towards her, which all come tumbling out in a most appropriate setting: a Brian McKnight concert. They end the night and their relationship (temporarily) in the venue’s security office, each staying true to what they want in that moment. Series creator Yvette Lee Bowser knew she had a singular couple on her hands, so she didn’t rush things, preferring a late-hour reunion in the series finale that was as heartwarming as it was a long time coming.[Danette Chavez]


9. How I Met Your Mother, “Matchmaker” and “Milk” (season one, episodes seven and 21)

Ted Mosby, desperate though he might be, is reluctant to turn to dating services for love. But when a matchmaker calculates the odds of him finding someone on his own (they’re not good), he signs right up, assured by the service’s 100% success rate. As promised, Love Connections quickly finds a near-perfect match for Ted… whom they’d already set up with someone else. Naturally, Ted tracks the woman down, only to find she’s about to get married, and that no made-up score is about to change her heart. Discouraged, Ted returns to his matchmaker to find her in a similar state of despondence, panicking that Ted is “going to die alone.” There’s an uplifting moment where Ted seems to coach himself though her, (“Hell, if a cockroach and a mouse can find love in this crazy city, then, damn it, so can I!”), and in “Milk,” he gets the call: He’s been matched with a woman who meets every point on his checklist. Ultimately, though, he realizes he doesn’t want the “perfect girl.” He wants Robin, and while no algorithm would ever place those two together, the strength of Ted’s feelings indicates that love isn’t something you can place a number on. [Maggie Donahue]


10. The Mary Tyler Moore Show, “Lou’s First Date” (season four, episode eight)

“You know those horrible phone calls you get when someone you hardly know calls you up and asks you to go out with somebody you don’t even know at all?” Mary Richards (Mary Tyler Moore) asks partway through “Lou’s First Date.” “Well, this is one of those phone calls.” The Twin Cities news producer has a winning line prepared in her attempt to connect her boss, Lou Grant (Ed Asner), with a date for an awards banquet, but in reaching out on Mr. Grant’s behalf, she doesn’t consider that there may be two Mrs. Dudleys at the number she’s cold calling. One Mrs. Dudley, Martha, is significantly older than the other (old enough to be her mother, even), and she’s the one who turns up at Mary’s before the awards—to Mary’s dismay, Lou’s frustration, and the shakily polite reactions of their co-workers. It seems further mortification is in store when Lou and Martha run into his recently estranged wife, Edie (Priscilla Morrill) at the banquet, but Lou has too big a heart to allow that discomfort to pass on to his date. With all the misunderstandings out of the way, “Lou’s First Date” is great spotlight for the teddy-bear side of Asner’s gruff performance, though he manages to get in one great, prickly zinger back at his wire-crossed matchmaker’s apartment: “All I said to you was, ‘Get me a date.’ I didn’t specify what kind of a date. How were you to know I wanted somebody under 90?” [Erik Adams]


11. The Marvelous Mrs. Maisel, “We’re Going To The Catskills!” (season two, episode four)

Screenshot: The Marvelous Mrs. Maisel

Most TV matchmaking attempts rarely yield more than the indignant eye roll or exasperated “Mom, stop!,” but Rose Maisel’s actually bear fruit. When she hears Benjamin’s mother say that he, a handsome bachelor and doctor, only dates weird girls, she chimes in to offer up her own peculiar daughter, and the meddling mothers spend the summer nudging their unwilling children together. Midge, knowing that a simple “no” won’t satisfy them, asks Benjamin on a very public date in order to get their parents off their backs. Though the date goes badly (mostly because Benjamin is an ass who refuses to row), Midge seems to have finally met her match in wit, if not in spirit, and the two eventually get together, making this a parent setup that actually kind of works. For the Maisels, after all, family is the most important thing: Everyone is drastically affected by any one person’s actions, so tied up in one another’s affairs that it makes sense that Midge and Benjamin would give it a real shot. [Maggie Donahue]


12. Taxi, “Louie And The Nice Girl” (season two, episode one)

“Louie And The Nice Girl” opens with an “only in a sitcom” prelude, where the entirety of the Sunshine Cab Company is excited to see someone they’ve never so much as spoken of before: Zena (Rhea Perlman), a candy-machine operator who’s as sweet as the contents of her hand truck. The whole garage loves Zena, but she only has eyes for loud, loutish dispatcher Louie (Danny DeVito). Once old softie Alex (Judd Hirsch) gets over his disbelief, he’s happy to help these opposites attract, leading to hotter and heavier things that your typical setting-up setup—at least the way Louie and his shredded wardrobe tell it. The truth is more complicated, as Louie lets on in a testy one-on-one drawing on the comic friction between DeVito and Hirsch: Louie and Zena haven’t actually gotten physical, because she’s the first woman he’s ever wanted to take on a second date. It’s always fun to see some vulnerability from DeVito’s petty tyrant; after filling a similarly caustic role for 11 seasons of Cheers, it’s even more fun to watch Perlman turn on the charm in her first go at a recurring role that put her and DeVito’s real-life romantic chemistry onscreen. [Erik Adams]


13. Golden Girls, “One Flew Out Of The Cuckoo’s Nest, Part 1” (season seven, episode 23)

Dorothy’s love life (or lack thereof) was the source of many jokes over The Golden Girls’ seven-season run, but she gets the last laugh in the two-part series closer, “One Flew Out Of The Cuckoo’s Nest.” Guest star Leslie Nielsen plays Blanche’s uncle Lucas, a charming Southern gent who’s rolling in the Hollingsworth money, but that’s not enough for Blanche to keep their plans. She tricks Lucas and Dorothy into entertaining each other for the evening while she does... what Blanche usually does. Over a crab dinner, Dorothy and Lucas decide the best way to get back at Blanche is to pretend that Blanche’s set-up worked a little too well. To everyone’s surprise, the romance becomes real, leading to a wedding and a big goodbye. It’s the stuff of fairytales, which is why it initially feels a bit out of place—but as Dorothy puts it, she was first rescued by her two best friends, Blanche and Rose, and her mother Sophia, so we already know who the real loves of her life are. “[Danette Chavez]


14. Cheers, “Diane’s Perfect Date” (season one, episode 17)

Some dates can be deadly dull—but others are just deadly. After betting they can set one another up with the ideal dates, Sam and Diane find themselves in an unsettling situation after he misinterprets her promise of bringing the perfect woman for him as being a secret way to date him herself. When she shows up with an uptight professor, Sam quickly grabs Andy, the first guy he finds in the back room of Cheers—and a total stranger who just so happens to have been recently released from jail after serving 10 years for manslaughter. Following a disastrous double date—Diane wants Italian food, but Andy warns them off a certain restaurant (“Bad memories, I killed a waitress there”)—Sam manages to pay off Andy and get him out of there while Diane cowers in the bathroom. It’s another round of signature Sam-and-Diane maneuvering to get the other to confess their feelings; unfortunately, Diane’s disinterest was a little too interesting for Andy, as he returned two more times to torment Diane with the threat of his affections. [Alex McLevy]


15. Sex And The City, “Drama Queens” (season three, episode seven)

In this season-three episode, Charlotte finds herself the only involuntarily single member of the group, and is typically obnoxious about it. She reads a book called Marriage Incorporated and decides to treat finding a husband like finding a job, hitting up her friends for “leads” and avoiding time burglars like her two happily involved friends (Carrie and Miranda, who explore new levels of intimacy in their respective relationships), and the Viagra-popping Samantha. A married couple offers to fix her up with their friend named Phil, who would be “perfect” for her, and Charlotte lives off that promise for the next week or so before spiraling out of control when her follow-up calls go unreturned. When she finally thinks she’s landed a date with the elusive Phil, it turns out to be a ploy by her married guy friend, who wants her for himself. The evening isn’t a total loss, though—Charlotte meets her soon-to-be first husband Trey after running from creepy married guy. [Danette Chavez]


16. Seinfeld, “The Fix-Up” (season three, episode 16)

There were other set-ups arranged on Seinfeld—the developing romance shown out of time in “The Betrayal” also comes to mind—but “The Fix-Up” centers George’s latest doomed relationship from beginning to end. When Jerry and Elaine decide to pair up their two friends who claim to have given up on dating, they learn just how many standards those friends still have: Cynthia wants a complete profile on George, of course, while he mostly wants to know if Jerry thinks Cynthia is worth dating. Still, Cynthia and George hit it off, and Jerry and Elaine promise to share any info they get from the new lovers. But when Cynthia seems to be ghosting on George, Jerry gets offended on his behalf while Elaine, who knows Cynthia is just worried about an unplanned pregnancy, takes her friend’s side over Jerry and George’s defective condoms. George briefly wins Cynthia back, only to lose her again when she notices his terrible table manners. [Danette Chavez]

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