10 Star Trek: The Next Generation Episodes Awkwardly Romantic Enough For Valentine’s Day

So you’re not into mail-order teddy bears or heart-shaped boxes of bonbons. Neither is the crew of the Starship Enterprise. There are plenty of reasons, human and otherwise, that Star Trek: The Next Generation wouldn’t be considered Valentine’s Day viewing. Androids like Data aren’t programmed to feel human emotion, and just a few minutes of getting to know Worf makes it clear the Klingon race will do just about anything to avoid it.

Even the homo sapiens on board (with the possible exception of Riker) aren’t exactly temptresses or Casanovas. Some need an operating manual just to get through a date, while others wouldn’t show affection if the Federation mandated it. Could you possibly imagine Captain Picard waltzing over to Dr. Crusher’s quarters with a bottle of Magus III’s finest vintage and a bouquet of chameleon roses? Point made. 

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Space fairytales aren’t about to happen when you’re beaming alien diplomats or racing across galaxies at warp nine. Still, the crew of the Enterprise tries to fumble their way through romance between all the Calrissian conflicts and Ferengi negotiations. From Riker’s interplanetary (and often interspecies) liaisons and Data’s failed attempt at programming human emotions to the embarrassingly amorous antics of Deanna Troi’s mother, it appears love in 24^th century space isn’t nearly as advanced as the technology.

“Haven” Season 1, Episode 10 (1987) 

Half-Betazoid Deanna Troi is mortified enough when her eccentric mother sends over a talking silver plaque from Betazed that publicly announces her daughter’s arranged marriage to human Wyatt Miller (and then vomits jewelry all over the transport deck). The atmosphere isn’t programmed for seduction when Deanna shows up in her fiancée’s doorway. Cold feet get even colder when he shows her his sketches of a mysterious blonde he’d been dreaming of since he could remember, a woman he thought was supposed to be Deanna until he beamed on board and saw she had the wrong hair color.

When the face in Wyatt’s dreams finally materializes onscreen when a Tyrellian ship encounters the Enterprise, he transports to his mystery woman and leaves Deanna to on-again, off-again paramour Riker (who was brooding over her engagement the entire time). This is also when Lwaxana Troi’s Betazoid-style pursuit for a mate has her first zeroing in on Picard—meaning, the captain is essentially doomed.

Moment of epic awkwardness: Just when it seems things can’t get more uneasy than an arranged marriage to another species, Deanna and Riker try for one last fling on the holodeck. Wyatt strides in with an underhanded insult in hand. The arguments between the future in-laws at the dinner table are also not to be missed.

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“The Dauphin” Season 2, Episode 10 (1989)

It doesn’t take long for Wesley Crusher to fall hard for the alien princess Salia after she is beamed onto the Enterprise—at least, she seems human(oid) enough. Even her pretty terrifying governess isn’t enough to make him want to beam himself to his room.

Wesley’s first mistake is running to the crew for advice, which ranges from Worf’s Klingon mating call to Data’s DNA compatibility analysis to Riker reciting excessively flowery (or in this case, starry?) poetry. Not that someone whose idea of setting the mood involves howling and throwing plates is the best person for a hormonal high schooler to ask for dating advice. A romantically inept android isn’t exactly a walking encyclopedia of love either, but Riker gets extra credit for his literary seduction skills. Wesley’s second mistake? He ignores all the warnings about what this teenage head-of-state crush has been hiding. 

Moment of epic awkwardness: When Wesley finally works up the nerve to kiss Salia, her governess seems to materialize in the doorway and morphs into something that could pass for a cross of Mothman and Bigfoot. Salia herself then turns clawed, fanged and extremely hairy. Talk about the most memorable first kiss ever.

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“Manhunt” Season 2, Episode 19 (1989)

The telepathic and always inappropriate Lwaxana Troi returns to the Enterprise in the throes of the Betazoid version of menopause, which sees her sex drive essentially quintupling. Her mate of choice? Captain Picard, who is put off by her blatant come-ons. Lwaxana’s version of hello is using her species’ advanced mind-reading abilities on Picard to expose his “naughty thoughts” in public. En route to the Pacifica conference as the representative for Betazed, she lures him into what is supposed to be an ambassadorial dinner for the crew (to which she only invites the mortified captain).

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When she starts making bedroom eyes—and suggestions—at dessert, Picard ups the awkwardness factor by inviting Data to interrupt their dinner date with sleep-inducing scientific anecdotes. He then escapes to a Dick-Tracy-esque program on the holodeck to make himself unavailable. Lwaxana pursues him, enters the program and starts seducing a mystery man who turns out to be no less holographic than the rest of the program. Picard out.

Moment of epic awkwardness: When Lwaxana starts making bedroom eyes (and suggestions) at dessert, Picard eagerly invites Data to interrupt their disaster date with sleep-inducing scientific anecdotes. The android soon launches into a doctorate-level lecture on satellites that makes Lwaxana Troi want to go to bed—for sleep.

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“The Emissary” Season 2, Episode 20 (1989)

Klingon dating 101, if a race that can attract a mate with a roar can even call it dating. Lieutenant Worf’s old half-Klingon, half-human flame, K’Ehleyr (pronounced Kay-lar) arrives to warn the crew about a potential threat. Never mind an impending battle; things on the personal front don’t exactly look too promising. Klingons are about as romantic as their battle grunts might suggest. Not to mention colder than an android in a freezer.

Worf is less than thrilled when Picard insists he and K’Ehleyr work together to fend off the potential feud, and starts growling when she slinks over to his computer and tells him to quit acting like a “Klingon glacier.” However, if there’s one thing that can melt this abominable snowman, it’s electric pink Spandex. He later prowls onto the holodeck and literally takes K’Ehleyr’s calisthenics program (if you could call fighting alien beasts in the jungle with a bat’leh calisthenics) to the next level.

Moment of epic awkwardness: When Worf tries to level up one more time by hollering traditional Klingon wedding vows, K’Ehleyr’s reaction to a shotgun wedding is all too human. She snaps that she will never be his wife and effectively kills the ambience.

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“Booby Trap” Season 3, Episode 6 (1989)

Lieutenant Commander Geordi La Forge programs an awkward enough beach rendevous on the holodeck, complete with Coco-NoNo cocktails and a gypsy serenade. When his date shows she is clearly not impressed with coconut rum or violinists in pirate boots and puffy shirts, he retreats to Ten-Forward with his visor downcast. La Forge loses himself in his work, heading to the Holodeck to figure out how to reconfigure the warp drive and save the ship from power losses.

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He programs the original version of the drive only to grow unreasonably infatuated with a 90-something-percent accurate hologram of its creator—the Enterprise’s original engineer, Leah Brahms. Even more awkward than a holographic romance a la Lwaxana Troi? In Galaxy’s Child (S4 E16), he meets the real Leah Brahms and learns she’s not only married (something her hologram neglected to say), but also aggravated at his modifications to the ship.

Moment of epic awkwardness: As if slowly falling for a disembodied computer voice isn’t creepy enough, LaForge keeps urging it to take on more and more of Leah’s characteristics until it finally gives him the holo version. Who cares if it’s off by a small percentage? 

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“The Vengeance Factor” Season 3, Episode 9 (1989)

Even the captain’s number one can be blinded by lust. When Commander Riker’s new Acamarian love interest refuses to open up to him, he assumes Yuta has either a fear of intimacy or a longing for her home planet’s cuisine. Evidently he misses that one detail about her people’s long history of blood feuds. it doesn’t seem that the shy humanoid blonde with the ridged forehead is capable of murder. Or is she?

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Things start to grow suspicious when an elder from an opposing clan drops dead from a sudden heart attack, and Dr. Crusher’s research reveals the culprit to be a genetically engineered micro-virus. Riker is skeptical until the database from Acamar III reveals an identical death from over 50 years ago—and its not-so-innocent perpetrator. Her anti-aging secret? Yuta confesses, to Riker’s horror, that she altered her cells to keep her alive long enough to eradicate everyone in the enemy clan. 

Moment of epic awkwardness: Riker’s phaser-point attempts to talk Yuta out of her revenge mission hardly have any effect. When he turns his phaser on her for the last time, it isn’t set on Stun. Cue the song I Used to Love Her (But I Had to Vaporize Her).

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“Ménage à Troi” Season 3, Episode 24 (1989) 

While Picard (mostly) dodges Lwaxana Troi this time, it’s now Lwaxana’s turn to get a proverbial taste of her own love potion when she is pursued by Ferengi officer Daimon Tog. She rejects the big-eared alien’s advances until she, Deanna and Riker are beamed aboard a Ferengi vessel—and have their dresses transported off. Lwaxana’s only hope for escape is seducing Tog’s access code out of him with an erotic ear massage.

When that doesn’t work, she strikes a deal with the Ferengi that allows them to keep her so long as Deanna and Riker are returned to the Enterprise. At Deanna’s urging, Picard halfheartedly plays the scorned lover, spewing Shakespeare until he manages to convince the Ferengi to hand Lwaxana over. Not that he intends to keep her on board. After she is beamed back and leaps into Picard’s lap, the captain extricates himself and commands Wesley to set course for Betazed—warp nine.

Moment of epic awkwardness: That ear massage. In human (and Betazoid) terms, the appeal of it is puzzling, but the ears are apparently the hottest Ferengi erogenous zone. Mrs. Troi gets major props for daring to touch those with freshly manicured nails.

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“Data’s Day” Season 4, Episode 11 (1991)

Never ask an android to be your go-between when it comes to matters of the heart. If Data and feelings don’t mix, inviting the emotionally challenged lieutenant commander to be in your wedding party is pretty much programming the big day for disaster. It might also be wise not to admit cold feet to someone who has the dictionary definition for the phrase stored in his database.

When botanist Keiko Ishikawa confides in Data that she wants to cancel her wedding to Transporter Chief Miles O’Brien right before the rehearsal, she also makes the mistake of asking him to talk to Miles. She hasn’t picked the best messenger. Data’s objective programming leads him to think that the decision to call the wedding off is good news. O’Brien is ready to deactivate Data when he matter-of-factly reports that Keiko “has made a decision to increase her happiness” by cancelling the wedding. Data backs off, and the wedding is back on.

Moment of epic awkwardness: Data’s attempts at learning to dance are hardly any less cringe-worthy than his grasping at emotion. He steps on Dr. Crusher’s feet most of the time when she teaches him, but the mechanical grin on his face when he finally gets it is priceless. 

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“Qpid” Season 4, Episode 20 (1991) 

How do you take one of the most epic love stories of all time and make it epically awkward? If you’re the limitless—and often tactless—Q, you beam the entire crew into Sherwood Forest and put Captain Picard on a Robin Hood mission to rescue Maid Marian (Vash, a romantic encounter from Season 3). After Q spies on Picard and Vash arguing over the former’s issues with expressing emotion, he zaps captain and crew to medieval England for a romance lesson of mythic proportions.

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Picard isn’t the smoothest operator in green tights. When he manages to break into the castle where Vash is trapped, he hardly makes a heroic show of throwing her over his shoulder and dashing out the window. Their fighting rouses the guards, who haul him off to the dungeon. Vash herself is later thrown in with him when she tries to escape on her own. Bonus: Worf as Will Scarlet and Data as Friar Tuck are the stuff of legend.

Moment of epic awkwardness: Vash and Picard argue so much as they march to trial, they hardly seem to notice they’re potentially destined for the executioner’s axe. They even keep at it during the trial (hardly the best way to keep one’s head attached). Ah, romance.

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“In Theory” Season 4, Episode 25 (1991)

It might not be the best idea to rehash your most recent breakup while configuring probes, but that is exactly what Lt. Jenna D’Sora does with an unsuspecting Data. She isn’t on the same wavelength. Anyone who robotically admits that said breakup has given him a fascinating glimpse into human intimacy clearly isn’t boyfriend material. Jenna still finds Data intriguing even after his fumbling attempts to understand emotion. He still isn’t quite sure what has just happened to him after she engages him in a halfway human kiss.

Data turns to the crew for his experiment. Based on what he can gather from a Klingon, a Betazoid and several humans, along with all the Shakespeare he can possibly read, Data programs himself to experience this mystifying thing called love. There are more than a few glitches, including obnoxious singing, even more obnoxious hyper-analyzing, and instigating a lovers’ quarrel. Program fail. 

Moment of epic awkwardness: The whole episode. There is absolutely nothing this android can get right about romance. Data critically analyzes everything, including a gift from his girlfriend, until she looks ready to delete his artificial love program right there and then.  

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This article first ran on Valentine’s Day 2016. We didn’t see any reason not to try again, though.