|It's really hard to say congrats without sounding sarcastic.|
|— Ann Perkins|
Leslie Knope hosts the annual Galentine's Day with her lady friends but feels bad that Ann Perkins doesn't have anyone with whom to celebrate Valentine's Day. She asks the Parks Department to set Ann up with someone at a Valentine's Day singles mixer that they are organizing. Chris Traeger, who is still depressed about being dumped by Milly, decides to DJ the mixer. Meanwhile, Leslie has given Ben Wyatt a Valentine's Day scavenger hunt filled with intricate riddles hidden all over Pawnee in order to discover where she wants to meet him that night, but she made it exceedingly difficult. Andy Dwyer and Ron Swanson help Ben out, and Ron turns out to be very eager and adept at solving riddles, despite his claims to the contrary. They agree to split up and find the riddles out of order to more quickly find the last one.
At the mixer, Chris plays depressing music that puts a sour mood on the event. Ann arrives and Leslie unsuccessfully tries to set her up with numerous men. April Ludgate, who dislikes Ann, refuses to help her, so Tom Haverford steps up to help Ann out, making Ann feel better with his humorous efforts. Chris tells Leslie he is sad because he is 44 years old and still single, believing Milly may have been his "personal best". Leslie cheers him up with a pep talk, but says he is also at fault for being single since as he was the one who broke up with Ann. Chris later plays upbeat music and everyone has a good time at the mixer. A grateful Ann decides to go home, but Leslie catches her applying make-up in her car. Thinking Chris was playing good music because he was in a better mood since he asked Ann out, Leslie follows them despite April's protests.
Ben, Ron, and Andy fail to find the last riddle, but Ron correctly guesses the meeting spot will be Li'l Sebastian's memorial site. Leslie tells Ben about Ann and Chris, and the two agree to catch them on a date to expose Chris' hypocrisy about workplace dating. To their shock, they find Ann on a date with Tom. April arrives, explaining she saw Ann laughing with Tom and convinced her to at least give a date with Tom a try. 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. Ron later sheepishly asks Leslie to do a riddle scavenger hunt for his birthday.
Donna: I have several men in rotation. One's waiting for me out in the car. Don't worry, I rolled down the window.
Leslie: Oh Ann, you beautiful spinster, I will find you love.
Ron: Thank you all for being here, let's get started.
Leslie: Wow, great attitude Ron.
Ron: Sorry, I was talking to these ribs.
Andy: April hates Valentine's Day. And brunch, and outside, and smiling. [laughs] She's weird.
Tom: Hey, Chris Cross, can we change up the music? It kinda sounds like the end of a movie about a monk who killed himself.
Chris: It is.
Ron: I hate riddles, and other such nonsense. I want that on record.
Leslie: How am I supposed to find the love of Ann's life when it sounds like a funeral in here?
Ben: Screw romantic dinners, let's go rub it in their face.
Leslie: God, I love you so much.
Ron: Leslie, thanks to your annoying prying last year, I'm sure you remember my birthday is coming up.
Leslie: I know, I know, no parties, you hate parties.
Ron: Correct. Oh, you know that wild goose chase you sent Ben on for valentine's day?
Leslie: The scavenger hunt?
Ron: I also do not want that.
Leslie: Yep, I understand.
Ron: I absolutely do not want to solve a series of riddles and clues each more intricate than the last. You understand what I'm saying?
Leslie: Yeah, I got it Ron.
Ron: Uh, I- I do want that. Please do that for me.