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1* SugarWiki/CrowningMomentOfHeartwarming: Gwendolyn telling Barbara that she’s been so moved by her book that she’s only having sex on her own terms and also is training to be become a pilot. And she says this all in front of Catcher, who up until this point she was only ever used by.
2* SugarWiki/FunnyMoments:
3** The whole OutOfContextEavesdropping bit, where Catcher’s new secretary, Sally, eavesdrops on them talking about what she thinks is the length of their penises (they’re talking about their socks). Cue Catcher saying, “Don’t forget, I’ve got two of them!”, and the secretary immediately passes out.
4** Barbara is left [[PostKissCatatonia so shocked the first time Catcher kisses her, she sounds hoarse the next time she speaks]]. Once she leaves, cue Catcher taking the wine cooler, taking the bottle out, going out to the balcony, and emptying the wine cooler over his head.
5** [[spoiler:After Barbara’s {{Infodump}}, which lasts three whole minutes in a single shot, we get a ReactionShot of Catcher, who has an absolutely priceless look of shock on his face.]]
6* GeniusBonus: Peter is shown making martinis by waving an unopened bottle of vermouth over a pitcher of gin and ice. This is a variation of the [[UsefulNotes/WinstonChurchill Churchill Martini]] which requires ice-cold gin and a bow toward France.
7* HilariousInHindsight:
8** A newsstand sells ''ComicBook/FantasticFour'' issue #16, which guest-starred ComicBook/AntMan and ComicBook/TheWasp. Eventually, Creator/PeytonReed (who almost directed ''Film/FantasticFour2005'') became the director of the ''Film/AntMan1'' movies.
9** At one point, there’s a scene where it shows a clip of Creator/JudyGarland singing “Down With Love” from a 1964 episode of ''The Judy Garland Show.'' 16 years after the release of ''Down With Love'', Creator/ReneeZellweger would go on to play her in the 2019 biopic ''Judy''.
10** The BetaCouple, Vicki Miller and Peter [=MacMannus=] both fret that they will never find a good man[=/=]woman to settle down with. Both Creator/SarahPaulson and Creator/DavidHydePierce would come out of the closet a few years after this film's release.
11* JerkassWoobie: Catcher. Given his treatment of women at the start of the film (consider the reactions of Gwendolyn and Yvette when they each find out that Catcher had been with them both the day before), the Jerkass part is there. But you've got to feel sorry for him at the end [[spoiler:when Barbara reveals she doesn't want to be with him and leaves him dumbfounded in the street.]]
12* RetroactiveRecognition: Barbara's city-slicker business partner? Why, she's none other than Ms. Creator/SarahPaulson, y'all.
13** Creator/ChrisParnell appears as presumably a NoCelebritiesWereHarmed version of John Daly, host of ''Series/WhatsMyLine''.
14* TearJerker:[[spoiler: Catcher and Barbara have eagerly agreed to get married, only for Gwendolyn to return and thank Barbara for what she has done for womankind. Cue Barbara BecomingTheMask, suddenly deciding she doesn’t want to be with Catcher, and walking out on him, leaving him dumbstruck and standing alone in the street as [[EmpathicEnvironment it pours with rain]]. Ouch!]]
15* TheyWastedAPerfectlyGoodPlot: So Barbara comes to the conclusion that she can be happy on her own and [[spoiler: leaves Catcher]]. For the viewer, this might be a perfectly good ending- the premise of the film is that love isn't all it's cracked up to be and you don't need it to be happy. Except, no, [[spoiler: she goes back to be with him]].
16* ValuesDissonance: Mostly DeliberateValuesDissonance, considering it’s all a satire of early 60’s culture, but [[spoiler: having sex under a false identity]] is technically rape.
17** Also counts as FridgeHorror, since Barbara [[spoiler: knew what was going on the whole time and apparently has no problem marrying the man who tried to rape her.]]
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