In my case, I envision the letter "S" in the beginning to reiterate that there were times in which the answer was simple: she just doesn't like me "that way."
I broke it down to each main character in the film since this is an ensemble piece:
Gigi (Ginnifer Goodwin): I had a hard time trying to sympathize with the character. She was the one who overanalyzed every nuance in a date. There were scenes in which she continually pushed the comfort levels of her dates with repeated phone calls and deconstructed criticism. Funny enough, all of the advice that she receives in the film does not include a key fact: Desperate aggression is a turn-off. She was at times two notches away from stalker status, as if her sole purpose is to find Mr. Right at any costs. But, she's a hopeless romantic who likes "Some Kind of Wonderful", and that can't be too bad.
Alex (Justin Long): Between this and "Zac and Miri", the actor is trying to distance himself from the geekiness of the Apple commercials (as well as "Dodgeball") and go for the Smoooooooth Operator persona. I like his character. No bullshit in telling you the truth. It's tough love with the "love" part gradually sinking in.
Conor (Kevin Connelly): Male counterpart to Gigi. A common theme of the film is that one person cares for another more than vice versa. Gigi pines over Conor while Conor pines for his "friend" Anna. (Like many traditional, fluffy rom coms, a straight male sees the attractive female friend as a consolation prize with the connotation of "the home game.")
Anna (Scarlett Johansen): Hard to watch her character, since she justifies flirting and having an affair with a married man. Again, we like to think that we are not so blind to wreck a marriage just for the possibility of finding "The One". You want to smack her head and scream, "What makes your relationship special if the man is willing to trivialize his marriage?) It's everything Chris Rock made fun of in his stand-up ("A man sees a woman with someone and says to himself, 'I want someone like her.' A woman sees a man with someone and says to herself, 'I want HIM! And I will slit that bitch's throat to get it.') After further seeing her scenes, I was dumbfounded at her anger when said married man cheats on her with his own wife. Wasn't even worth the skinny dip. Christie Brinkley did it better in "National Lampoon's Vacation".
Ben (Bradley Cooper): Between this, "Failure to Launch", and "The Hangover", the actor is in danger of being typecast as the Player. He's does the cheating jerk role quite well.
Janine (Jennifer Connelly): The actress does seriously, emotionally stunted roles well (see "Requiem for a Dream", for example). As the wife, she receives more exposure and normally in these films as the anatomy of the affair is addressed. The problem is that the character isn't exactly sympathetic, so all parties lose.
Beth (Jennifer Aniston): She pretty much plays Jennifer Aniston, only a little more serious. To her, a 7-year commitment isn't enough. The concept of marriage out of peer pressure is never fun to watch. (Youngest sister is getting married, why can't I? WAAAH!) However, the chemistry with Ben Affleck works. Weird.
Neil (Ben Affleck): Emotionally mature. The ideal boyfriend minus the need to marry. He cares through actions rather than words. If anything, one wonders why is he seeing Beth. However, as stated, the chemistry works.
Mary ("Drew Barrymore"): It was probably after this film that she decided to no longer due such comedies, hence "Grey Gardens". It showed. Her character was probably there to address how cyberspace further complicates dating (i.e. using Myspace/Facebook/LJ/Twitter/Dreamwidth to find that soulmate.)
Overall, one must remember two things after seeing the film: (1) the less serious you take dating, the happier you will be, and (2) avoid genearalized pronouncements on how supposedly all men or all women think.