- Misled by Holly’s insinuation that Julia is Only in It for the Money with Glenn, Robbie starts acting like a jackass, thinking that’s what Julia likes. It ends up breaking her heart and nearly bringing her to tears (he basically accused her of being a gold digger). The worst part is when Robbie picks up the stack of papers she threw at him just before storming off. Turned out she had made personalized sheet music for him! While the scene is partially played for laughs (“I AM an ass-HOLE!”), the fact that he almost lost his chance with her because of Holly’s meddling and his very poor choice of words hits hard. In a non rom-com setting, that kind of mistake could easily kill any chance of a relationship, and Robbie would have been thinking and agonizing about that moment for years and years afterwards.
- Robbie after being jilted at his wedding, especially the part where he is told the news by his sister and when he breaks a mirror in rage.
- Robbie's voice starting to crack upon seeing so many happy couples of various ages at the first wedding he works at after the break up.
- Robbie goes to tell Julia how he feels but sees her talking to herself in the mirror and assumes she's happy to be with Glenn. He leaves, heartbroken.
- Sammy pouring out his heart to Robbie.Robbie: That's it, man, starting right now, me and you are going to be free and happy the rest of our lives!Sammy: I'm not happy. I'm miserable. (Slams his whiskey)Robbie: ...What?Sammy: I grew up idolizing guys like Fonzie and Vinnie Barbarino because they got a lot of chicks. You know what happened to Fonzie and Vinnie Barbarino?Robbie: Yeah, I read that Fonzie wants to be a director and Barbarino, I think...the mechanical bull movie? I didn't see it yet.Sammy: Their shows got canceled because no one wants to see a fifty-year-old guy hitting on chicks.Robbie: So what are you saying?
http://tvtropes.org/pmwiki/pmwiki.php/TearJerker/TheWeddingSinger
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