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  • Alternative Character Interpretation: After all, which are Jill's feelings for Hal? At the beginning of the film she rejects him, revealing with brutal sincerity that she is not attracted to him and considers him shallow. Days later, she is surprised to see Hal dancing with unattractive women (to him) and shocked to meet his new girlfriend, Rosemary. After catching Rosemary leaving Hal's apartment the next morning after the couple's first night of sex, Jill immediately begins to flirt shamelessly with Hal, even though she knows he's dating seriously. At their date in the third act, Jill says she was wrong about Hal and makes a comment that can be interpreted as malicious, saying that she saw the appearance of Hal's recent girlfriends and realized that he is pathologically unshallow. So has Jill always been in love with Hal and seeing him having a serious relationship with Rosemary aroused her feelings and made her decide to fight for her love? Or was Jill jealous of seeing Hal happy with a woman who is the exact opposite of her physically and saw Jack more as a trophy?
    • Also, Jill when she convinces Hal to go out to dinner together as friends. She passes it off as a change of plans because her girlfriend bailed on her, but one does have to wonder if she was simply trying to impress Hal into having a date with her.
    • Also, Rosemary herself. There's a lot of emphasis on how "sweet" and "kind" she is, but she seems to have some rude and judgmental tendencies of her own, which may be an attempt to deflect her own feelings of inadequacy with humour. Consider the following exchange:
    Hal:I bet on horses sometimes, but I don't really care about the money.
    Rosemary: I never read that book.
    Hal: What book?
    Rosemary: Things losers say.
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    • Rosemary's feelings for Hal. She initially thinks he's mocking her, and it's only the morning after the monologue "I know I'm not pretty" that she apologizes, decides to trust him and start dating seriously. The movie makes it clear that Hal is her first serious boyfriend, with his previous relationship being more of a platonic friendship. Did Rosemary really fall in love with Hal or she see him as her only chance to have a serious love relationship in her life? Or is it a mixture of the two possibilities?
  • Esoteric Happy Ending: The film shows Hal abandoning his routine, work and friends to stay with Rosemary at the Peace Corps. In turn, Rosemary forgives Hal and the two date again, and will probably marry. The problem is: Rosemary doesn't know about Hal's hypnosis yet, so she'll probably never know that their relationship initially started with a lie. Hal, in turn, may have difficulty adjusting to his new life away from home, and he saw the real Rosemary for just one day. And that doesn't mean that he is now physically attracted to fat people. How long will it be before Hal and Rosemary's marriage becomes strained to issues of low sexual chemistry?
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  • Evil Is Sexy: At least when the hypnotism is off.
  • Harsher in Hindsight: Tony Robbins hypnotizing Hal to see the inner beauty in people can be seen as this after this Buzzfeed report reveals that he berated abuse and rape victims and hit on his female subordinates.
  • Narm: Some of Rosemary's dramatic scenes lamenting her obesity and the negative consequences this has had on her love life can be a little silly when you see the lines coming from the mouth of a thin Gwyneth Paltrow.
  • Narm Charm: That said, Gwyneth Paltrow really does a nice job with the material she has, which can make up for this problem.
  • Special Effects Failure:
    • Towards the end where Rosemary is carrying Hal, you can see that parts of his shirt are fastened to strings.
    • When Hal and Rosemary reconcile at the party at the end and hug each other, pay attention to Rosemary's arms and you can clearly see where the fat suit ends as her hands are perfectly slim.
  • Tear Jerker:
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    • During the hypnosis, Hal saw Cadence as a perfectly healthy and beautiful little girl. After it's turned off, he sees her again... with burns all over her face. He looks up, and what does Hal see? "Pediatric Burn Unit."
    • The way Rosemary talks about how she knows she's not pretty and how no man has ever loved her like Hal does will definitely hit home if you are or know a woman who has ever had body image issues.
  • They Wasted a Perfectly Good Plot: Jill, Hal's beautiful neighbor, begins to be jealous after seeing him and Rosemary dating, starting to blatantly flirt with Hal. This subplot could have a higher screentime, but is eventually relegated to a few scenes. Rosemary and Jill end up having just one scene together, and the plot of Rosemary suspecting that Hal has an affair with Jill ends without conclusion.
  • Took the Bad Film Seriously: The film is just OK, but Gwyneth Paltrow stands out in the cast and does a great job showing Rosemary's many facets, especially her depression over the way obesity has damaged her love life and her happiness alongside Hal.
  • Unfortunate Implications: In his review of the film, Roger Ebert acknowledged a comment he received pointing out that, despite the film and its trailers emphasizing the importance of inner beauty, Hal's perception of "inner beauty" is seeing nice but unattractive people as beautiful super models while also seeing attractive but mean people as really ugly, which in many ways are just as, if not more, shallow and insulting than if Hal had just rejected Rosemary because of her looks.
  • Unintentionally Unsympathetic: Mauricio, Hal's shallow, snarky best friend who is responsible for Hal's hypnosis spell ending just because he wanted him to be superficial again. Even after we learn his Freudian Excuse that he was born with a tail that, since it has an artery wrapped around it, can't be surgically removed, it doesn't garner him much sympathy, mainly due to him spending most of the movie badmouthing Rosemary and how absolutely gross his condition is.
  • Values Dissonance:
    • For chubby chasers and people who aren't put off by transsexuals, Hal's judgement of both as ugly is sure to be this.
    • Gwyneth Paltrow playing both thin and fat Rosemary may be this to many viewers who find the fat suit offensive, and believe that a fat actress could have been cast in these scenes.
    • With a huge chunk of beautiful people being perceived as ugly, it also lends to the unfair "pretty people are jerks" stereotype.
    • And some find the reverse stereotype "ugly/average looking people are saints" patronizing.
  • The Woobie: Rosemary, who has been humiliated and rejected by men for so many years that, when Hal starts flirting with her, she takes time to believe him and thinks he's just mocking her. And then she realizes he's telling the truth and they both date seriously, having the best times of her life ... just to Hal start to avoiding her without any explanation. And then she sees Hal having dinner with a beautiful, thin woman, and that totally destroys her.
    • Also Cadence, along with all the other burn victims.
  • WTH, Casting Agency?: Jack Black as Hal. Yes, the intention of the movie is to portray Hal as a hypocrite because he demands such beauty in women when he himself is far from conventional beauty standards. But still, his contrast to the idealized Rosemary in the movie would be bigger with a more conventional actor of romantic comedy.
    • Gwyneth Paltrow as fat Rosemary in a fat suit may also be that for viewers who think it would be better if the filmmakers had cast two different actresses, one for thin Rosemary and the other for fat Rosemary.

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