Is There A Script Doctor In The House? The film has a number of very good performances, some good Chicago locations and generally good set design, and is otherwise technically well made from a behind the camera standpoint but gets a low grade on the basis of the story and script.
This review is based on the DVD, not a theatrical presentation, so I will reference some of the bonus material including the "alternate" ending (which should actually have been termed the originally ending on the DVD -- "before we were forced to re-shoot it because the test audiences hated and didn't buy it!")
I could get past the initial set up of the film, which has (as Gregory House might have put it) a woman of a certain numeric rank being hit upon by a man of a far lower numeric rank) because generally movies written by guys have that as their basis all the time (which is why we see hot girls with schlubs all over movies and TV shows constantly) but also because, frankly, some women often just frankly have bad taste plus women seem to have a higher threshold with their gag reflex of what the male version of a dog is than males do about females. But once you get past that surface, as people, it's pretty clear that Brooke and Gary are wrong for each other, well before the dinner party that causes the "final straw" to set up the rest of the movie. This is where I think the story and script fail the audience.
While the montage of snap shots between the two leads was a good way to showcase the development of their relationship, the baseball meeting (rather than meet cute) was the wrong set up, since it was really more "meet annoying" or "meet obnoxious," One of the deleted scenes has the Vince Vaughn character helping a very attractive female buy her drink at a club (the same club which is shown in the movie itself, where Gary's brother Lupus - Cole Hauser's character - took him to help him meet women). In this deleted scene, the Gary character is funny and it is readily apparent how a women could be either entertained or charmed enough to go out on a date with him. In the opening baseball scene, in addition to being out of character for the date Brooke is with and for Brooke herself, it also fails to create the impression necessary to set up the rest of the movie.
The next time you see the characters, before and at the dinner party, you clearly see they do not make a good couple for any number of reasons, certainly not good enough for the other key set up of the film -- to live together in a piece of property they both decided to purchase jointly, even prior to marriage.
While the film could have been made about a apartment under rent control in say Manhattan in such a great location, neither party wanted to give it up, plus also recognizing how hard it would be to find a great apartment by themselves in the New York market. Otherwise, it's hard to understand why THIS couple would decide to live together by buying property together.
Giving Gary some sort of redeeming quality would have helped. Sure, his male friends could bond with him and think he's a great guy - even a stranger who came to date a very attractive female (Brooke) could be so distracted by Gary's ability to be a great male friend that this stranger (Brooke's date, Mike) could lose out on an attractive female. But these scenes don't show Gary to be a good friend to any females, much less an attractive or appealing partnership opportunity for Brooke or any other woman. Also, again this scene is an example of how the movie is badly written. Why would Gary make nice with a more attractive guy going out with his ex within a fresh less than two weeks of his breakup, when a few days earlier, he was trying so hard to embarrass Brooke in front a less attractive (and therefore less threatening) male escort with tricks on how to get Brooke to put out or what sex scenes and sex play she was into?
The script isn't strong enough for the number of points it tries to make. Some of the scenes added, especially for comedic effect, are totally unnecessary where other scenes could have been used to better effect (a key example is the entire first scene of Justin Long's character answering the phone at the art gallery). I think ultimately they decided those were needed to make the film commercially viable -- not to make it a better film.
This was a possibly average to decent drama or possible decent to solid comedy that needed to be focused and sharper in story, plot and details, but also needed a script doctor to really improve the plot, something which the director was apparently not able (or possible not allowed?) to do, given his commentary on the DVD, particularly with the original ending of the movie, as written and as this director shot it, especially to end the film with a very extended musical number after the dialogue between Brooke, Gary and their respective dates at the open air festival.
The alternate ending (that was released) of the film is what keeps the entire film from being a dismal bomb, something so obviously apparent, that hearing the director defend the original ending is surprising.