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* TechBro: This episode has a subdued, romantic version in Joshua, the young, good-looking, charismatic founder of a booming dating app[[note]] the column it was based on was explicitly about Hinge CEO Justin [=McLeod=][[/note]].
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* NoCelebritiesWereHarmed: The original column was written about Justin [=McLeod=], the founder of the dating app Hinge. Here he is represented by a man named Joshua.
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Your Cheating Heart is an index, not a trope.
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* YourCheatingHeart: Emma cheated on Joshua with her high school boyfriend, which is what caused them to break up in the first place.
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[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ml_02.png]]
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!!Tropes in this episode:
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!!"When Cupid Is a Prying Journalist"
->''"I did want to ask, though, have you, have you ever been in love yourself?"''
Dating site founder Joshua (Creator/DevPatel) tells the story of his lost love Emma (Creator/CaitlinMcGee) to journalist Julie (Creator/CatherineKeener). Julie herself tells him the story of her own "what if?" with Michael (Creator/AndyGarcia).
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* IKissYourHand: Michael kisses Julie's hand at dinner.
* IvyLeagueForEveryone: Subverted; Joshua claims he's from Harvard to look successful before giving it up and admitting he didn't go to college.
* LoveAtFirstSight: Sparks fly between Joshua and Emma at their first meeting, and Julie outright calls it this in her article.
* NewOldFlame: Julie and Michael reconnect in middle age. While their meeting inspires Michael to work on his less-than-ideal marriage, Julie leaves her husband.
* TheOneThatGotAway:
** Emma is Joshua's; even after they broke up he still thinks of her and is shaken when he encounters her on the street.
** Michael is Julie's, as she took a memento of their summer together to every relationship and well into her marriage. Evidently she was his as well, as he comes to her book signing and later admits that she was his only old flame.
* VoiceoverLetter: The excerpt of the article on Joshua Emily reads is in Julie's voice.
* YourCheatingHeart: Emma cheated on Joshua with her high school boyfriend, which is what caused them to break up in the first place.
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->''"I did want to ask, though, have you, have you ever been in love yourself?"''
Dating site founder Joshua (Creator/DevPatel) tells the story of his lost love Emma (Creator/CaitlinMcGee) to journalist Julie (Creator/CatherineKeener). Julie herself tells him the story of her own "what if?" with Michael (Creator/AndyGarcia).
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* IKissYourHand: Michael kisses Julie's hand at dinner.
* IvyLeagueForEveryone: Subverted; Joshua claims he's from Harvard to look successful before giving it up and admitting he didn't go to college.
* LoveAtFirstSight: Sparks fly between Joshua and Emma at their first meeting, and Julie outright calls it this in her article.
* NewOldFlame: Julie and Michael reconnect in middle age. While their meeting inspires Michael to work on his less-than-ideal marriage, Julie leaves her husband.
* TheOneThatGotAway:
** Emma is Joshua's; even after they broke up he still thinks of her and is shaken when he encounters her on the street.
** Michael is Julie's, as she took a memento of their summer together to every relationship and well into her marriage. Evidently she was his as well, as he comes to her book signing and later admits that she was his only old flame.
* VoiceoverLetter: The excerpt of the article on Joshua Emily reads is in Julie's voice.
* YourCheatingHeart: Emma cheated on Joshua with her high school boyfriend, which is what caused them to break up in the first place.
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