The kids go through the joys and pains (well, mostly pains) of Valentine's Day.
Tropes:
- Abhorrent Admirer: In the end, Andrew's horrid behavior pushes Missy away, and causes her to lose any interest in him.
- Amicable Exes: Gina and Nick become these when they have a respectful, civil conversation with one another at Lola's party.
- Armor-Piercing Response: When Andrew tells Missy that he knows that she still likes him, her response afterwards makes him realize that his behavior has drove her away.Andrew: Missy get your coat, we're fucking going home, you like me!
Missy: Not anymore. (Andrew is shocked) - Asshole Victim: Andrew's decent into toxic masculinity ends with the girl of his affections rejecting him, having all of his hair ripped out by the root until he looks like his bald father, then getting kicked out into the rain as a party of onlookers film him crying. All things considered, he brought it on himself.
- Awful Wedded Life: The Gloubermans, even more so than usual. Marty is downright hateful about Valentine's Day and makes it absolutely clear that he is more interested in watching the Knicks game. He screams at Barbara and waves money in her face (similar to how Andrew did so with Missy) before dragging her off to dinner, which he insists will take no more than 45 minutes so that he can be back in time to watch the game.
- Bait-and-Switch: It seems that Andrew is going to Lola's party to apologize to Missy for his possessive and jealous behavior, but quickly reverts back to that same behavior by the time he arrives at Lola's party.
- Big Bad: Andrew becomes the main antagonist in this episode, since his personality is at his worst here and drives the conflict with his actions with everyone else, including Maury, becoming disgusted with his actions, especially when he tries forcing Lars out of his wheelchair.
- Bittersweet Ending: Nick learns to accept Connie as his hormone monster and is back on speaking terms with Gina, while Jessi and Matthew enjoy each others company during Valentine's Day. However, Nick's relationship with his parents becomes tense, Andrew pushes Missy away, and Jay is forced to break up with his pillow and couch cushion.
- Bizarre Alien Biology: Maury's penis-shaped nose goes erect once Matthew gets another guy's phone number.
- Call-Back:
- Andrew's crush on Diane Lane is brought up again. It turns out he first met Maury while watching one of her movies.
- After being briefly alluded to in Season 1, we finally get to see Maury being Matthew's Hormone Monster.
- Jessi does a fist pump while saying "life is a fucked up mess" during the Valentine's Day song.
- Nick and Jessi are exasperated by Andrew's Kangol hat persona. Nick openly complains that Andrew builds these personas around whatever hat he's wearing. This is a callback to Andrew with his "jazz hat" and the "pimp hat".
- Judd's trained raccoons show up again in a less violent role.
- Maury mentions Marty's huge balls again.
- Brother–Sister Incest: There's a subplot involving conjoined brothers in an incestuous relationship.
- Character Development:
- Jay's storyline is mostly separate from the other characters, and is focused on his realization that his obsession with sex and "relationships" with inanimate objects are just ways of avoiding having to deal with the real issues in his life.
- Nick finally rebels against his parents' smothering affection and starts asserting himself, which Leah approves of.
- Jessi comes to terms with her mother having moved on from her failed marriage, finally letting go of her anger.
- Matthew proves that he is a good friend to have and that he's not just young, gay and mean.
- Andrew develops in a negative direction, going from a nice kid to being outright violent towards others.
- Condescending Compassion: After Missy compliments his hat, Andrew just responds with condescension.
- Continuity Snarl: Connie was supposedly kicked off Jessie's development, yet we see that they still hang out.
- Crazy Jealous Guy: Andrew towards Missy. He massively overcompensates when he thinks that Missy is seeing Lars, including buying her candy he should know she can't eat due her well-established bad reaction to sugar. When Lars points this out it only increases Andrew's jealousy.
- Does This Remind You of Anything?: Continuing with the Season 2 finale, Nick and Connie's relationship plays out like a typical love story. Matthew also has this with both Jessie and Maury.
- Dogged Nice Guy: Inverted. Andrew thinks he's this near the end of the episode, when in all reality he's turned into a major Jerkass throughout the entire thing.
- Entitled to Have You: After Missy gives Lars a Valentine's card (as a friend), Andrew gets very possessive over her. In the season two finale he had glimpsed her record on Maurice's computer in Human Resources and it indicated that she still had a thing for him. Based on this he literally shouts at her that he knows that she's into him and he demands that she accept that fact despite his increasingly scary behavior.
- Epic Fail: Andrew's attempt to draw Missy's attention by jumping up to touch a door jam fails and results in him hurting himself.
- Everyone Has Standards: Even the likes of Maurice, Matthew, and Devin are put off by Andrew forcing Lars out of his wheelchair to humiliate him. Though in Maury’s case, he gives up trying to convince Andrew that Lars really is handicapped, supports him in throwing Lars off his wheelchair and even directs Andrew to Lars’ seatbelt in his chair.
- Andrew had this too at the beginning of the special, though his toxic masculinity was at a relatively low level, when he is against Maurice murdering his bandmates when they agree to come to Lola’s party without Andrew since she 86’d him from it.
- Fan Disservice:
- Nick's dad has no shame talking about his vagina-scented breath.
- Maurice is still having flashbacks to the time he saw Andrew's dad's scrotum.
- Freeze-Frame Bonus: During Jay's Imagine Spot to be the "Ultimate Fuck Machine", there's a title card that says his occupation is 40-year-old magician.
- Gayngst: Matthew is self-conscious about being the only openly gay kid at school on Valentines Day. Luckily for him, he runs into a boy his age in a similar predicament at Wallgreens. Also discussed when Jessie vents her frustrations to him about her mother's relationship with another woman and he tells her that her mother still deserves to be happy.
- Humiliation Conga: Andrew's Jerkass, and indeed outright violent, behavior at Lola's party horrifies everyone to the point that nobody takes his side, not even Nick. Then Lola tears off Andrew's hat, which had been giving him a bad allergic reaction and this results in ripping out much of his hair so that he is partially bald. Finally, he has a freakout on the street, embarrassing himself while most of the kids video it from inside.
- Ignored Epiphany: Andrew realizes that he's turning out like his dad, but when he goes to apologize to Missy, his hormone-addled rage when seeing her with another boy causes him to act even worse. By the end of the episode, most of his hair gets ripped off, making him look bald.
- Imaginary Love Triangle: Andrew thinks that his crush, Missy likes Lars and vice-versa, when in reality the two are just friends. It gets to the point where Andrew's growing jealously towards Lars and possessiveness towards Missy causes Andrew to attack the former, while pushing away the latter from Andrew.
- Inelegant Blubbering: Nick's sudden rush of estrogen causes him to start crying hysterically over things he'd normally be more controlled over.
- Intellectual Animal: Judd has trained his raccoons to the point where they can serve as cooks and waiters! One of them even takes a cigarette break before delivering a course and two others have a conversation with each other.
- It's All About Me: Andrew falls victim to his own ego over the course of the special. This is best illustrated in his Dream Sequence, wherein he imagines a future where Missy is a famous Jazz musician receiving a Grammy award — and she tells the audience that Andrew, her manager and lover, is the one who really deserves it and that she would never choose to be with anyone but him. Even when he realizes that he's made an ass of himself in front of Missy, he seems more concerned that he's turning into his father than whether or not he's actually hurt anyone.
- It's Always Spring: Mid-February in Westchester County, New York, should not be that green, nor have as many people walking around in short sleeves.
- Jerkass Realization: Andrew realizes too little, too late that acting like a possessive jerk would drive away Missy for good.
- Kick the Dog: Andrew attacking Lars, a handicap kid. He earlier verbally attacked Caleb for pointing out his Entitled to Have You behavior, as well.
- Laser-Guided Karma: Because of his acting very violent and possessive towards Missy, Andrew ends up pushing her away before Lola, Andrew's ex-girlfriend, rips his hat off with most of his hair attached, completing his transformation into his own father. Lola then throws Andrew out of her apartment, and Andrew then takes out his violent frustration on inanimate objects, hurting himself in the process, while everyone else laughs at his suffering.
- Leaning on the Fourth Wall: Jessi gets Matthew to admit he hired another voice actor to do her in their song and dance number because she (or her voice actress) had previously stated that she wasn't comfortable singing.
- Magical Queer: Jessi genuinely enjoys spending Valentine's Day with Matthew even though he's gay. He even orchestrates a fantasy Friendship Song and dance at dinner. Matthew then helps Jessi accept her mother's relationship with Dina on the premise that finding love, even when you're middle-aged, is a good thing. Given Jessi's depression storyline at the end of the last season, this is all very good for her.
- Men Don't Cry: Andrew and Jay are downright baffled and even a little disgusted when their seemingly-friendly teasing drives Nick to tears.
- My God, What Have I Done?: Andrew actually blurts out the "What Have I Done" part when he realizes that he has pushed Missy away with his actions.
- Noodle Incident:
- At some point Devin and Devon got back together, for better or worse.
- It’s heavily implied that they got back together after “Steve the Virgin”, with them talking selfies together after Gina calls them out on adding to Nick’s humiliation.
- The ladybug mentions being a single parent whose partner had died.
- At some point Devin and Devon got back together, for better or worse.
- Not Good with Rejection: Andrew goes full-on nuts when Missy makes it clear that she just wants to be friends. He has multiple outbursts, terrifying Missy in the music room and later attacking Lars at Lola's party.
- Oddly Specific Greeting Card: Jessi and Matthew look for Valentine's Day cards and find a whole section for conjoined incestuous twins, saying things like, "Two hearts sharing the same beat, two souls sharing the same feet." This becomes a Brick Joke when a pair of conjoined twins end up on a date at the same restaurant as Jessi and Matthew.
- Oedipal Complex: Connie accuses Nick of having one of these when buying a Valentine's card for his mother and, later, going to a Valentine's Day dinner with them.
- Pay Evil unto Evil: Lola tears off the hat attached to Andrew's scalp, resulting in the loss of most of his hair, before literally throwing him out of her party, all of which happens after Missy completely rejects Andrew. Considering how much of a jerk he was being, it's hard feeling bad for him.
- Parental Incest: Connie gives Nick crap over buying his mother a Valentine's card by saying he wants to fuck her and give his dad a BJ.
- Parents as People: As Matthew explains to her, Jessie may wish that her parents were still together, but she should accept her mother's new relationship if it means she's allowing herself to be happy.
- Prince Charming Wannabe: Andrew desperately tries to come across as the perfect guy for Missy, but in the process just acts violently and possessive.
- Product Placement: Walgreen's is a prominent location in the special. Coach Steve now works there and the kids shop there. It also includes a Take That! at the competition: "We make CVS look like Rite Aid".
- Say My Name: Andrew shouts Missy's name at the end of the episode.
- Shout-Out:
- The entire episode has many references to When Harry Met Sally....
- Andrew's fall from grace can be a reference to Black Mirror's very own "Nosedive".
- Sexophone: Connie's...emissions make this sound.
- Stunned Silence: Most of the kids react this way while Andrew is attacking Lars, if only because the sudden violence is in such stark contrast to what had been an otherwise very civilized party that they seem unsure of how to handle it.
- Throw the Dog a Bone: After missing so many baskets, Andrew finally makes one and breaks the fourth wall to ask the viewer to watch it again, but then negates that and tells them to continue watching.
- Took a Level in Jerkass: Fueled by a sense of entitlement once he finds out she still has feelings for him, Andrew becomes extremely possessive of Missy, going as far as to throw Lars out of his wheelchair when she gives him attention, then grabbing her by the hand and yelling at her. Even before this, he has no qualms teasing Nick to the point of tears in public or yelling at Caleb when he tells Andrew that he's becoming possessive.
- Vocal Dissonance: When Leah repeats "Aloe vera", she suddenly speaks with Connie's voice.
- What Have I Become?: After getting most of his hair ripped off and being told that he now looks like his dad, Andrew realizes too little too late that he's becoming just as much of a jerk as his father is.
