- Jerry: Leslie, you can't actually plan your future. I mean, there are no guarantees in this world. As long as the people that I love are a part of my life, I will be just fine.
It's Halloween in Pawnee. Diane invites Ron to go trick-or-treating with her and her girls, and Ron reluctantly agrees, taking Andy with him. Andy is practicing his observation skills in preparation for his police exam, and carries a tape recorder to describe general things around him. Diane gets called away on an emergency, and Ron is forced to meditate in a dispute between Diane's daughters. He ends up making them cry. Diane leaves an angry voicemail for Ron, and he wonders if he's able to date Diane with her kids being part of the picture.
Leslie and Ann view houses for Leslie and Ben to move into once he returns from Washington DC. After viewing a few, Leslie believes she's found the perfect place and writes up a lease with the seller. In Washington, Ben announces that the campaign he has been working on is complete, and they have won. While April leaves immediately to return to Pawnee, Jennifer Barkley talks to Ben about his future career, offering him the opportunity to work on another campaign. However, when he tells Leslie, she is upset, as she was counting on him returning to Pawnee shortly. Ben promises that everything is still preliminary.
Leslie goes with Ann to Chris' Halloween movie screening at City Hall to get her mind off of Ben's news. At the screening, Donna loudly comments on the movie, as well as live-tweeting her reactions to it. Leslie discusses her problems about Ben with Ann, who suggests they scare Tom, who has just left the movie screening to use the bathroom, to cheer her up. However, Jerry is the one who comes out of the bathroom, and when they startle him, he has a heart attack.
When Diane later apologizes to Ron for snapping at him, Ron does not reciprocate, causing her to part ways with him. After April and Andy call him out on his actions, he changes his mind and goes to Diane's house with gifts. He apologizes, explaining that he has spent most of his life alone and is not used to children. They all then go trick-or-treating again, despite it being a week after Halloween.
Feeling guilty about causing Jerry's heart attack, Leslie sets up a charity sale to help pay Jerry's medical bills due to how bad their health insurance policy is. Tom tries to sell some of his designer clothing, but when a woman says she can't buy her son these nice clothes because he would outgrow them too fast, he comes up with an idea for a new business: renting his designer clothes out to preteens and teenagers. Ann sells off the items and clothes she accumulated from her past relationships. Disappointed by the low amount they've raised, Leslie conducts an impromptu auction for a date with Ann, which immediately gets out of hand.
Leslie tells Jerry they've raised a little over $1200 from the sale, which he's happy about, but Leslie still feels bad, projecting her own fears about her unstable future onto Jerry. However, he reminds her that you can't plan the future. Meanwhile, Jennifer and Ben have a meeting about him beginning to run a new campaign. She advises him to "think about your future".
The next day, Leslie is viewing the house a final time before canceling her lease on it. Unexpectedly, Ben arrives and proposes. Leslie accepts, and the two embrace.
Tropes
- Bachelor Auction: Leslie conducts an impromptu one during an auction of items for charity, and auctions off a date with Ann (with Ann's partial consent). However, when it's won by a hairy, middle-aged biker guy with tattoos and a tank top, Ann promptly bids a million dollars on herself, declares herself the winner, and exits stage left.
- Bread, Eggs, Breaded Eggs: When Ben tells Leslie about the job offer in Florida.Leslie: Florida? They have sharks in Florida. And swamps. And swamp sharks.
Ben: ...Do you mean alligators?
Leslie: Maybe. - Chuck Cunningham Syndrome: After he was Put on a Bus in "Freddy Spaghetti", Mark essentially seemed to be forgotten about, if not erased altogether. In this episode, the crew assembles a sale to raise money for some of Jerry's medical bills and Ann contributes by selling off several items she collected from her previous relationships; she has a box of items for every other ex-boyfriend she's had except for Mark, even though they had dated for most of the second season.
- Deadly Prank: Downplayed - Leslie and Ann's prank of jumping out to scare Tom winds up with them accidentally scaring Jerry, which triggers a heart attack in him but they're able to get timely medical intervention and save him.
- Double-Meaning Title: Refers both to Jerry's heart attack and Ben proposing to Leslie.
- Halfway Plot Switch: The first half of the episode involves an office Halloween party, but then as a result of Leslie and Ann scaring him, Jerry has a heart attack, and the rest of the episode involves Leslie holding a charity auction to raise money for Jerry and his family.
- Halloween Episode: The first half of the episode deals with the characters dressing up in costumes and celebrating the holiday, with Ron going trick-or-treating with Diane and her daughters, a horror movie night being held at city hall, and Leslie and Ann's attempt to pull a prank going badly wrong.
- Pun: Tom really just wants the doctor to say Jerry had a "fart attack".
