Gretchen and Jimmy go out to brunch where they run into Edgar and Lindsay. Jimmy pretends to be angry at having to deal with Sunday Funday with the gang, but it turns out he and Edgar are in cahoots to trick Gretchen into having a fun Halloween by doing a list of "morbid and perverse" things that he thinks Gretchen would enjoy doing.
The group goes costume shopping. Outside of the costume store, Lindsay runs into Paul, who is dressed very realistically as Stephen Hawking. She mentions that she had to move into Becca's since Paul abandoned her. Paul chastises her, telling her that one day she'll learn not to quit when things get hard.
Jimmy dresses up as "Heathstead from Buckle Your Shoes" (a fictional British comedy) and tries to explain the show to Edgar, who doesn't get it or know what he's referring to.
Lindsay complains to Gretchen that she can't find a costume; Gretchen points out that she's hardly even looked. Lindsay tells Gretchen what Paul said about her giving up too easily and asks if that's true. Gretchen gives a bunch of examples in agreement.
Jimmy shows Gretchen his costume. She doesn't get it either. She seems distinctly down in the dumps and when Jimmy tries to get her excited about what costume she'll buy, she just glumly chooses a pair of wings with no real interest. Jimmy tries to get her to rent an elaborate costume for her but she declines. Seeing how sad she is, Jimmy rents the costume for her anyway after she walks away.
Edgar tells Jimmy that he's nervous because he hasn't had sex in three years and that he and Dorothy have gotten "close" (over the bra stuff, specifically). Jimmy laughs at him.
The group leaves the store, all in costume.
The group goes on a Hollywood Murder Tour. Gretchen brings up Edgar's long time since last having sex. Edgar wonders whether he should just be honest and tell her, but the group laughs at him and warns him not to, making fun of what the first time would be like after such a long dry spell. Gretchen wonders why Edgar would put a Murder Tour on his list.
The Murder Tour visits the site of Biggie Smalls' murder. Lindsay vents her problems to a Biggie Smalls Impersonator while Gretchen, Jimmy, and Edgar use an iPad version of a Ouija Board to ask the ghost of Biggie who shot him. It seems as though the board is about to say Tupac, but ends up spelling out Tupal.
The group next goes to a Spice Girls drag cover band concert, which ends up having been canceled because one of the performers (Herschel Houlahan aka Baby Spice) had to get an emergency prostate surgery. Gretchen continues to be suspicious about why Edgar would put a Spice Girls concert on his list. He feigns being a fan, but ends up only naming one song which Gretchen calls him out on.
Dorothy shows up dressed as Steven Spielberg. She makes a bunch of Spielberg puns and then kisses Edgar, much to the disturbance of the other friends who didn't recognize her in costume. Jimmy assumes she'll recognize his costume but she doesn't. Edgar resists making out with her.
Jimmy and Edgar talk about Edgar's nervousness regarding Dorothy. He tells Jimmy that he's just not ready if he goes too far with her he'll need to tell her about his problems. Jimmy tries to convince him that it's important for him to end his period of sexual frustration but Edgar disagrees.
Gretchen interrupts, asking to go home, but Edgar and Jimmy tell her that it's time for the "grand finale."
The group goes to a haunted house where a man in a pig mask wearing military dress aggressively briefs them on the fact that once they go through the door there is no exit and no safe word. The group enters to an empty room, thinking it's not that scary, until the lights cut out and the haunted house actors wreak real, terrifying havoc on them. Gretchen cheers up noticeably, clearly having a blast.
Gretchen and Jimmy run into Vernon, who tells them he's a horror house nerd and is going to another one later with a real Babadook. Gretchen and Jimmy sit on a couch, out of which come hands that pull them into another room.
Meanwhile, Lindsay, covered in blood and clad only in her undergarments is tormented by one of the haunted house workers who is playing a Buffalo Bill character. She gives up on trying to get out, and vents to him about being a shitty wife and shitty homeowner. He suggests she call customer service to sort out the power problem.
Vernon has bugs shoved into his mouth and projectile vomits, shouting 'Hell yeah!' gleefully at the haunted house 'fun.'
Edgar is panicking in the haunted house. Dorothy tries to calm him down. He ends up beating up one of the haunted house workers who spooks him. Dorothy pulls him off and he confesses that he has PTSD from his combat experience as well as that he hasn't had sex in three years. Dorothy is understanding, and leads him away by the hand.
A couple walk through the haunted house. The man thinks that the haunted house is derivative, and the woman counters that horror films are legacy. The man points out that it's the golden age of TV and that TV owns. They open another door to find Edgar and Dorothy having sex. They back away, horrified.
"Buffalo Bill" gives Lindsay advice to break up a problem into smaller "chunks" to solve it. He walks her through how to call the electric company and asks if she'd like him to do it for her. She tells him she can do it herself and he sends her phone down to her in a basket.
Gretchen happily discusses how much fun she's had. Jimmy confesses that he "knew" it would work and that the day he planned would snap her out of her funk. Gretchen blows up at him for thinking he can fix her and for wanting to. Jimmy angrily "apologizes" for trying to give her a nice day and walks away from her.
Lindsay finds Gretchen, who tells her what Jimmy did. Lindsay points out that of course he tried to fix her because he's Jimmy, and that he won't stop. Gretchen has the idea to pretend he's already fixed her so he'll stop trying.
Jimmy bumps into a girl who recognizes his costume and they bond over the show. She introduces herself as Nina Keune who owns the bar and has been serving Jimmy for months. Jimmy apologizes for not recognizing her, noting that he doesn't recognize people. She comments that maybe she'll join him when things cool down at the bar, so they can continue discussing the show.
Gretchen finds Jimmy and caters to his ego, telling him that he was right and that all she needed was a fun day to snap her out of her funk. She notices that he has two glasses and wonders how he knew she was coming. Nina, approaching the table presumably to drink with Jimmy, sees Gretchen sitting there and after exchanging a glance with Jimmy, she walks away. Jimmy and Gretchen talk and laugh about the haunted house.
Lindsay makes her way back to her house, which has been ransacked by Halloweeners. She notices that all of the electricity has been turned back on and smiles happily.