Leslie holds her annual "Galentine's Day" brunch for her friends on February 13th. Ann is the only one in attendance who isn't currently in a relationship. Feeling bad for her friend, Leslie decides to find someone for Ann. Later, Leslie holds a meeting with the Parks Department to finalize plans for a Valentine's Day singles mixer being held at the rec center. She also informs everyone that they need to bring an eligible bachelor to the party for Ann to date.
Ben gives Leslie her Valentine's present, a stuffed animal based off a dream that she had. In return, Leslie has a cryptex puzzle for him that will tell him where they will meet tonight for their date. He just has to crack the code, but he can't even open it.
Chris is still depressed about being dumped by Millicent. He does not approve of Tom's choice of DJ for the dance, so he offers to do it himself.
Andy offers to help Ben with the cryptex. He suggests they ask Ron. Ron smashes the cryptex open to reveal the clue hidden inside. Ron solves the riddle and the three of them realize this is a scavenger hunt. They search for the next clue and realize Leslie made it exceedingly difficult and long. Ron easily solves many of the clues, while making sure that everyone understands that he hates riddles and puzzles. They find out there are two dozen clues left, so they split up to cover more ground.
At the dance, Chris plays weird depressing music that puts a sour mood on the event. Jerry accidentally brought a male escort for himself. April has brought in her weird friend Orin, earning her a calling out from Leslie. When Ann arrives, Leslie sets her up with different men, all of whom are inappropriate in their own ways. Tom tries to cheer Chris up so he'll play less depressing music, but it doesn't work. Leslie decides to cheer up Chris, so she puts April and Tom in charge of finding a guy for Ann.
Chris laments to Leslie that he's 44 years old and still single, believing Millicent may have been his soulmate and he's afraid of being alone. Leslie gets him back up with a pep talk, and thanks to her efforts, Chris puts on happier music and everyone has a good time at the dance. Ann thanks Leslie for spending the dance trying to find her a date, but she's ready to call it a night and go home. Leslie decides to take her out for a drink, but she sees Ann in her car putting on lipstick. Leslie tells April that Ann has a date, and guesses that it's with Chris. Leslie decides to follow Ann, upset that Chris is dating an employee after Ben had to quit for dating Leslie. April tries to talk Leslie out of it. Leslie goes to meet Ben.
Ben, Ron, and Andy failed to find the last clue. Ron figures out that, since Leslie loves to be right, the special location is somewhere that she was proven right. Ben guesses that it's the memorial for Li'l Sebastian. He meets Leslie, and she tells him about Chris and Ann. He gets upset for the same reasons she did, and they decide to catch them in the act. They arrive at the restaurant and are shocked to see Ann is actually with Tom, not Chris. April shows up and tells them she set up Ann with Tom because Tom cheered Ann up during the mixer and that he's at least somewhat cool. Leslie is touched that April helped Ann out. Leslie and Ben leave Ann and Tom alone on their date, which Ann quickly admits was a mistake after Tom reverts to his usual chauvinistic attitude.
Later, Ron approaches Leslie to warn her against giving him a scavenger hunt for his upcoming birthday. She says she understands, but he then has to admit that he really wants her to do it for him.
Tropes
- The Bear: Alluded to when Ron has to go into The Bulge and receives a lot of favorable looks.
- Briar Patching: Ron makes a pretty obvious attempt at this at the end, telling Leslie that he absolutely does not want her to set up a scavenger hunt for his upcoming birthday, so definitely don't do that, whatever you do. (He then breaks down and admits that he does, in fact, want that.)
- Brother–Sister Incest: Implied with one of the men Leslie tries to set Ann up with.Jeff: Leslie, you didn't tell me she was so beautiful!
Ann: Aw, thanks, Jeff!
Jeff: Not as beautiful as my sister, but... you know the law. - Comically Missing the Point: Jerry went on Craigslist to find a date for Ann, only to wind up getting himself a male escort for the night.
- Cutting the Knot:
- Leslie gives Ben a cryptex
containing a clue to where to meet her for their date on Valentine's Day. Ben can't figure out the five-digit combination and asks Ron if he could solve it. Ron just takes out a hammer and smashes it to pieces to get the clue. - Similarly, when the scavenger hunt turns out to be very long and complicated, Ben suggests they simply go to places where the clues are likely to be and hope they happen to find the last one.
- Leslie gives Ben a cryptex
- Date Peepers: Ben and Leslie.
- Hidden Depths: Both Ron and Andy prove to be good with Leslie's riddles. Ron loves riddles and Andy loves Leslie so between them they're really good at figuring out what she was getting at. Special points must go to Ron though, as he figured out a 30-letter anagram in about 90 seconds.
- I Resemble That Remark!: Ron states that he hates riddles before solving the current clue in a heartbeat and enthusiastically coming up with a game plan to find the rest.
- Oh, Crap!: Leslie has sent Ben on a scavenger hunt for clues about their date. Upon the discovery that there's a third clue, Ron asks, "Just how many clues are there?" Ben shoots a wide-eyed Aside Glance.
- Scavenger Hunt: Leslie sets one up for Ben.
- Strange Minds Think Alike: Both Ron and Andy guess that the answer to a clue about what Ben and Leslie did on a date is "fuck". Or rather, "fucks," because the cryptex requires a five-letter word.
- "The Reason You Suck" Speech: Leslie gives one to April for not taking her assignment to find a guy for Ann seriously, with Leslie pointing out that if the situation was reversed, Ann would help her even though April's constantly a jerk to her.
- Valentine's Day Episode: The episode features Leslie's annual "Galentine's Day" luncheon and the Parks department's Valentine's dance.
