If you're going to get involved with somebody you work with, you got to be prepared for the consequences...
— Jackie
Everybody of the Jump Street team struggles with romantic love issues in a different way.
- Judy finds out her new boyfriend is actually deliberately hiding from her the fact that he is married. When she breaks the romance off because of this, he turns into a Stalker with a Crush towards her, and worse, tries to get the entire Jump Street team down through his workplace influence. Because he's actually a municipal official sent to audit the Jump Street team, this might affect the whole team.
- Penhall's girlfriend Dorothy throws him out of their house and their relationship ends. Having no other place to live, Penhall moves in with Ioki for a while. But they soon find out that living together is much more difficult than "just" being co-workers, and they get on each others' nerves. And all of that notwithstanding, they get assigned together to find a guy who flashes himself—which requires Ioki to cross-dress.
- Hanson and his girlfriend Jackie feel that they want to go do something "adventurous" (go on an exotic vacation/trip) to spice up their relationship, but they can't agree on how and when this can happen.
This episode provides examples of:
- Disguised in Drag: Ioki has to dress up as a woman, which includes wearing a wig, panties, pumps and lipstick, in order to catch a suspect who's exposing himself. This coincides with his bickering with Penhall about their grievances of living together, which accentuates their Heterosexual Life-Partners roles in this episode.
- Office Romance: Played for Drama with Judy. She starts a romance with a sort-of co-worker (a municipal employee who has to review the Jump Street officers). Turns out he's married and deliberately concealed that fact to her; upon which she breaks up with him. Then he turns into a Stalker with a Crush, stalking her with telephone calls and, when she refuses to continue the romance with him, outright lying on his report about her / the Jump Street program. This trope is also conversed In Universe, as Judy's story, once Hanson finds out, gets Hanson and Jackie (themselves in an Office Romance) talking about Office Romances, their viability and dangers.
- Stalker with a Crush: Judy starts a romance with a man; when she finds out he actually is married and deliberately concealed that fact to her, she breaks it off. Upon which he turns into a stalker—keeping calling her despite her wishes, lying on a report he has to file about her / the Jump Street team, blackmailing her...
- Valentine Day Episode: Deconstructed. Though the word "Valentine" isn't uttered in the episode, its original air date was February 12th and its title and, more importantly, every plotline in it, is about romantic love. But not the positive sides of romantic love: one is about the aftermath after a romantic relationship ends, one is about how a romance turns ugly when it is based on a lie, and one is about that relationships need work to keep them lively.
