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1* BrokenAesop:
2** Beth wants Neil to marry her, but he doesn't believe in marriage, and she breaks up with him as a result. Beth soon realizes what she's lost and asks Neil to take her back. It appears the Aesop is that that marriage doesn't automatically make you happy or more committed than a devoted couple. And in the end, a woman can find happiness without it. [[spoiler: However, Neil then asks Beth to marry him anyways. Apparently, a woman can't be complete without marriage after all and men ''will'' always marry a woman if they love her.]]
3*** Or that the guy has to bend over backwards to keep a girl who doesn't share the same aspirations as him. Very rarely does this actually work. [[spoiler: As we see with Ben and Janine.]]
4*** Or the general idea they both sacrifice their dreams for their significant other. For better or worse. Though some would find that romantic.
5** Alex and Gigi. Alex spends most of the film drilling into Gigi (and the audience) that if a guy wants to be with you, ''he'll make it happen''. If you're not sure whether or not he likes you, or have to do all the work to be together, then [[TitleDrop he's just not that into you]] and you should move on. No exceptions, not even you. Toward the end of act two, Gigi then dissects every interaction she ever had with Alex, and convinces herself there were "signs" he was secretly into her, which he calls her out on before he sends her away. [[spoiler: And then it all flies out the window when it turns out Gigi was right. Alex ''did'' secretly like her, and she ''is'' his exception, completely breaking the film's ''entire premise''.]]
6* TearJerker: Janine, upon discovering that her husband cheated on her with Anna, immediately starts assuming it's ''her'' fault for not being "fun" anymore even when Gigi and Beth try to tell her it's not.
7* UnintentionalPeriodPiece:
8** This film is practically a time capsule of what dating was like right before the explosive popularity of smartphones in TheNewTens, and with them the rise of dating websites and apps, specifically in Gigi's story.
9** Some aspects of the film already looked dated when it came out, given it was shot in 2007. Most of the young cast still had landline phones in their homes, and had work numbers that they gave to dates. The film shows voicemail as the primary communication method, and the existence of text messaging is only briefly mentioned. Mary's rant about being rejected on seven different devices also became dated fairly quickly when smartphones consolidated it down to one for most people.
10** This film also came out at the latest possible time anyone was still using [=MySpace=].
11* UnintentionallyUnsympathetic: Everyone in the Anna/Ben/Janine triangle:
12** Janine: Willfully ignored from the very beginning that Ben wasn't that interested in her and essentially forced him into marriage by giving him an ultimatum.
13** Ben: Didn't have the balls to tell Janine that he wasn't that interested in her and married her rather than breaking up with her, then cheated on her rather than having the balls to divorce her first. He’s definitely the worst of the three.
14** Anna: Yes, the ClosetShuffle Ben pulls on her is humiliating. But she was fully aware that she was sleeping with a married man. Did she really expect him to be faithful to ''her''?
15* TheWoobie: It's hard not to feel bad for Gigi when Alex tells her that yet another guy doesn't like her.
16-->'''Gigi''': So, what? Now I'm just supposed to run from every guy who doesn't like me?
17-->'''Alex''': ''Yes''.
18-->'''Gigi''': ...There won't be anyone left.

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