It's Valentine's day but nobody, except Judy, of the Jump Street team has a date. Hanson is being grumpy about hating Valentine day, and is having a fight with his girlfriend Amy about this. Hanson, Penhall, Ioki, Fuller and Sal decide to spend the evening together playing poker. While doing so, each tells the story of their "worst date ever".
- Sal was caught by the father of his then-girlfriend when they were 16 and trying to have sex; they never got to that, but were forced to marry by the father (and still are happily married).
- Penhall tells how he once had a Two Timer Date with two women—twins, no less—which got out of hand. Then he admits he made that story up because he "never had a bad date in his life".
- Fuller tells a more serious story, about how he cheated on his wife with a police officer co-worker while on police duty and was caught for that, and how this ended his marriage.
- Judy (who by now has returned to Jump Street from her date) tells how horrible her date (on that very same night) was: the guy was doing karaoke but was a very bad singer.
- Hanson begrudgingly tells his "worst date" story last: he went to a Valentine high school ball as a 16-year-old. His father, who was a police officer on duty that night, was murdered by a man robbing a cafe that night, and at the end of his date, 16-year-old Hanson found that out.
After Hanson's story, everybody's shocked. He says he's o.k. though, and the whole team goes out to have a beer with each other in a bar.
This episode provides examples of:
- Agony of the Feet: Mr. DeAngelo's bowling partner drops a bowling ball on DeAngelo's foot; he recoils in pain in response.
- Breather Episode: This episode basically is about the characters reminiscing about bad dates over a poker game on Valentine's Day, and it is much lighter in tone than the preceding Very Special Episode about a teenager with Aids.
- Cop Killer: Part of Hanson's backstory, as revealed in this episode—his father was a cop who was killed on the job by a robber one Valentine's day when Tom was in high school. It's heavily implied this backstory is what made Hanson become a cop himself.
- Curse Cut Short: When Mr. DeAngelo gets a bowling ball falling on his foot, he yells "Son of a—" but is interrupted by his bowling partner before he can end that.
- Food Fight: During a Poker night, everyone starts throwing food items from the bowls on the table, at Penhall, when he reveals a story that he just told them was made up.
- Good Angel, Bad Angel: Conversed by Penhall, when he tells that when he considered having a Two-Timer Date with two twins, he had an angel on one shoulder and a devil on the other shoulder, whispering in his ears (the devil won).
- I'm Going to Hell for This: After telling a story about the time he had an affair with his partner back in the 70's and getting ridiculed by the other guys for it, Captain Fuller points out that they're all going to hell anyway for playing poker in a church.
- Mood Whiplash: The first four stories, and the mood of the episode in general, are more breezy and comedic; but when Hanson gets to tell his story at the end, it is much darker and much more of a tearjerker than the rest.
- Overprotective Dad: When Rosa's father finds a half-undressed Sal alone with his daughter, he makes the couple marry the next day, apparently not taking any chance at all that sex might have happened (but it hadn't).Sal: [Upon being discovered; nervous and awkward] Hi Mr. DeAngelo!Mr. DeAngelo: [Sternly but not unfriendly] Call me Dad from now on.
- Parents Walk In at the Worst Time: Downplayed: Teenage Sal and his then-girlfriend want to have sex for the first time when she is home alone because her father is out bowling. When her father unexpectedly comes home early, he walks in not on them making out anymore (they heard him coming), but he finds their clothes scattered all over the floor and a half-undressed Sal, so it's clear to him what they were doing.
- Shotgun Wedding: Sal tells how he was rushed into marriage at a very young age by an angry father who caught him and his then-girlfriend fooling around, even though nothing sexual had actually happened between them (though it wasn't for lack of trying).
- Twin Threesome Fantasy: The story Doug tells ends with two twin sisters inviting him to come home with them for the night (sex very heavily implied). He then tells he made up this story... which proves even more that that apparently is a fantasy of his.
- Two-Timer Date: Doug tells the story of his having a date with two women (twin sisters, no less) at the same time without them knowing. He keeps running from one to the other, until he can't keep it up anymore and pulls a Screw This, I'm Out of Here!.
- Valentine's Day Episodes: The episode takes place on Valentine's day, and it features all of the characters (except Judy) NOT going out on a date but playing poker with each other in the Jump Street Chapel while telling each other stories of earlier (Valentine) dates gone wrong (and at the end, even Judy shows up to tell how her own date on that very same day went wrong).
- Whole Episode Flashback: Most of the episode does not take place in the present day, but in flash backs. Each character is telling about a bad date they once had, and they're all shown in flashback (even the downplayed example of Judy, who's telling about a date that happened on the same day—it's still shown as a flashback).
- Your Cheating Heart: Captain Fuller tells that the reason he got divorced, is that he cheated on his wife with a fellow police officer.