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1* {{Adorkable}}:
2** Although following the ''spirit'' of Hitch's advice, Albert mainly manages to charm Allegra by being who he really is...which involves bad dancing, teaching her to whistle, and dropping mustard on his shirt.
3--->'''Hitch:''' So, wait...that stuff ''worked'' for you?\
4'''Allegra:''' It was adorable.
5** Allegra is herself quite adorkable at times - particularly in the boardroom scene where she asks for money to pursue a project.
6** Hitch himself in his college days was an awkward late bloomer who dressed like a dork...and still managed to get a beautiful woman to date him (if only briefly).
7* AlternateCharacterInterpretation: Is Hitch a good guy that's just providing some romantic hand-holding to other good guys that need it? Or is he a morally gray person that gives sound dating advice but also engages in tactics that are fundamentally deceptive and manipulative? While Sara was wrong for assuming Hitch was an asshole based on nothing, a case can be made that despite his altruistic motives, some of Hitch's practices can genuinely come off as shady and underhanded, and that he's being a little intellectually dishonest when he denies any wrongdoing.
8* AluminumChristmasTrees: There exists in real life a "Pick-Up Artist" culture of men who consider themselves skilled at wooing women. Some of them are manipulative and unrepentant [[{{Jerkass}} jerkasses]] like Vance, while others are genuinely nice guys like Hitch who coach clueless guys on how to become less clueless about women. In some ways, the ending of this movie is a {{Deconstruction}} of this "Pick-Up Artist" culture.
9* SugarWiki/FunnyMoments: Several, most notably Albert's dancing prowess and Hitch's food allergy incident. The end credits feature the entire cast dancing insanely at [[spoiler: Albert and Allegra's wedding]].
10* SugarWiki/HeartwarmingMoments: When Albert and Allegra and Hitch and Sara reconcile.
11* HoYay: There's one scene where Hitch is showing Albert how to kiss and pretends to be Allegra, and has him practice a good night kiss scenario. Romantic music even plays during the scene. HilarityEnsues when Albert ''actually'' kisses him and Hitch reacts with horror and disgust.
12* RetroactiveRecognition: Vance Munson is played by Creator/JeffreyDonovan, who plays Michael Westen on ''Series/BurnNotice'', which makes it [[HilariousInHindsight even funnier]] when Hitch manages to physically overpower him.
13* StrawmanHasAPoint: The title character makes some very valid points about continuing with one's life, adapting, and moving on after a relationship goes sour. He gets called out on this by one of his clients who outright calls him a coward for not chasing after one's love; granted, in the client's case, the breakup was because of a misunderstanding, but on Hitch's case there was a very clear and valid reason for it. As expected, since the film is a RomanticComedy, Hitch gives in and goes great lengths to get back his love interest even after several rejections, incurring extreme behavior and injuries to himself. Try imagining how that would work in RealLife.

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