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1[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/rainydaynyposter.jpg]]
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3''A Rainy Day in New York'' is a 2019 romantic comedy film directed by Creator/WoodyAllen.
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5Gatsby Welles (Creator/TimotheeChalamet) is the son of wealthy parents and studies at Yardley College. He has a girlfriend, Ashleigh Enright (Creator/ElleFanning), a daughter of Arizona bankers who is majoring in journalism. She gets the opportunity to interview a lauded film director, Roland Pollard (Creator/LievSchreiber), in Manhattan. Gatsby accompanies her with plans to spend a romantic weekend with her. However, his plans are derailed when Ashleigh gets too involved in the director's creative crisis, leaving Gatsby to his own devices. While roaming the city, he meets Chan (Creator/SelenaGomez), the younger sister of an ex-girlfriend of his, and spends time with her instead, while also catching up with friends and avoiding having to attend his mother's party.
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7!!Tropes:
8* AnnoyingLaugh: Gatsby visits his brother who says he can't stand the way his fiancée laughs. Gatsby sees what he's talking about just before he leaves and even turns to look in surprise when he hears it.
9* BedroomAdulteryScene: Ashleigh and Francisco are about to have sex together at his apartment, when Francisco's girlfriend shows up unexpectedly. Ashleigh has to hide and is eventually trapped outside without her clothes.
10* BelligerentSexualTension: Gatsby and Chan are quite snarky with each other, but Gatsby realizes she is a better match for him than Ashleigh eventually.
11* BettyAndVeronica: Gatsby ("Archie") is in a LoveTriangle with his girlfriend Ashleigh ("Betty"), a naive girl from Arizona who studies at Yardley College with him, and Chan ("Veronica"), a snarky New Yorker. Finally, he chooses Chan.
12* CreatorBreakdown: InUniverse, with Roland feeling so disgusted by his new movie that he runs out of a screening in distress, sending Ashleigh and his screenwriter Ted in search of him through the city.
13* TheDitz: Ashleigh comes across as a giggly airhead. While she does seem to have an extensive (albeit flawed) knowledge of cinema and emotional intelligence, she doesn't always get Gatsby's references, which is a reason he dumps her for the savvier Chan.
14* EducationMama: Gatsby often laments that his mother has always been very demanding in regards to his education and jokes that she would pop a cyanide pill if something doesn't meet her high standards. Turns out she used to be a call girl, so maybe she has reasons to be demanding.
15* HomeEarlySurprise: Francisco's girlfriend gets back home earlier than planned and arrives just when he is about to have sex with Ashleigh.
16* NakedPeopleTrappedOutside: When Francisco's girlfriend shows up unexpectedly at his apartment, Ashleigh has to hide and is eventually trapped outside without her clothes.
17* ProfessionalGambler: Gatsby has no clue what he wants to become after college, but in the meanwhile he makes a killing at poker. He's earned $20,000 through it at the start of the film, allowing him and Ashleigh to stay at a ritzy hotel in New York and splurge on other things.
18* RomanticRain: Gatsby strongly believes that walking in the rain is the most romantic thing ever. A reason he gives for breaking up with Ashleigh is because she's more of a "sunny" girl, and gets with Chan, who shares his affinity for the rain. In the end, he and Chan kiss while they're out in the rain.
19* ShesAllGrownUp: Chan is the younger sister of an ex-girlfriend of Gatsby's. Having not seen her in a while, he's rather impressed with how she turned out.

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