Alternate Character Interpretation/ Fridge Brilliance: In the scene where Rosie has a viewing party, Dylan uses his phone to take a picture of Brianna's chest. This basically makes him seem like a jerk, and is used to garner sympathy for Izzie (from both her mom and the audience). However, a few days after watching the movie it occurred to me that not long before that, Izzie had told her mom that she and her friends had gotten Dylan to play Truth or Dare. It's possible Dylan had received a dare to do what he did, which Izzie probably wouldn't have heard if it happened while she was talking with her mom. Which makes sense if you consider that right as that conversation was ending, Dylan and a friend of his came up to the two of them wanting to make sure Brianna was going to be at the party. The timing of their question could indicate the dare had just been made a moment ago. I'm not sure how much any of this would mitigate Dylan's jerkdom at accepting the dare, but if he was only doing it out of a desire to play by the rules of the game Izzie herself had wanted him to play... *shrug*
To contrast the above example, I provide the following as an example of my definitely being slow on the uptake, and not at all as clever as a refrigerator: It was a few days after seeing the movie before it suddenly occurred to me that what Izzie and Mel said in the scene where they made a crank call to Matthew Perry was based on the theme song from his show.
Awesome Music: Saoirse Ronan's rendition of "Moronic" is very nice. It's this in-universe too.
Crosses the Line Twice: When Izzy is getting rid of her Barbies, Rosie gets uncomfortable because the pile of naked dolls reminds her of a concentration camp.
Izzy tries to haggle it down to fifteen. Rosie relents and says seventeen is okay. Izzy responds "fifteen is the new seventeen."
When the two are playing with the Barbies, the scenario is a Soap Opera esque wedding interruption. Rosie gets uncomfortable because Izzy has her 'character' insult the other's fashion sense - so she backtracks and tries to change the scenario to them making friends.
Izzy: Why is she suddenly being nice?
Rosie: She's manic depressive.
Rosie's ex-husband asks her if she has any dates. When she replies in the negative, he says completely seriously "you have got to get over me already."
Rosie thinks Adam is cheating on her and Nathan walks in, casually talking about how one knows when Rosie is really mad - as her voice gets high-pitched. Which it has.
Nathan: After my Bachelor Party, only dogs could hear her.
Adam: I believe it.
Nathan also compares the situation to a Love Triangle with him as Bruce Willis, Adam as Ashton Kutcher and Rosie as Demi Moore. They get sidetracked wondering how to properly pronounce Demi's name. Rosie interrupts with her voice now very high.
"I am not Demi! You are not Ashton! And YOU! (points at Nathan) You are definitely not Bruce Willis!"
When Rosie discovers that Izzy and Mel crank called various celebrities, Rosie starts falling apart. Izzy suggests her own punishment: writing an apology letter to everyone she called and not using the phone for a week. Rosie changes it to one month, but Izzy advises "that's excessive; two weeks" and Rosie agrees.
Girl Show Ghetto: The movie was in Development Hell for ages because producers worried nobody would want to see something about a 40-year-old woman. This could have been the reason it was pulled from a the planned theatrical release and sent straight to DVD (though it did play theatrically in some places).
Hollywood Homely: Subverted. Rosie is desperately trying to cling to her youth and worries that she's being judged for her age - but the only character who actually says this is Mother Nature, who's annoyed at any person who tries to preserve their youth. Rosie's romance with Adam would contradict this. For added effect Michelle Pfeiffer was seven years older than her character is supposed to be.