The movie is like a short-story, almost like an episode in a standard romantic/funny series. One episode is described, very few characters.
The plot is about a guy who is stuck in his old tricks when he really falls in love with a girl. You can guess the rest of the story from that sentence.
Some reviews I have read tells this is a guy sweet-talking a girl to a one-night stand, and afterwards falling in love (the standard story). But I like to take what happened in the beginning as "a fact", a girl meets a boy, they are interested in each others, the boys character and history complicates the situation.
So, it is not really a very complicated or enriching or anything, but it is a fair try to make a romantic movie.
Most of the main characters are built good enough. Both Danny (Dean Paras) and Peter Angelo (David DeLuise), along with other people from Danny's past are described through a look-back which works. They both play their roles well. Tim (Stefan Brogren) is presented as a mix between a heterosexual gay person, a strange artist, a looser and an a**hole. He is a bit too weird. Corey (Katie Wright) is an adorable "normal girl", by other reviews accused of being naive - but she isn't really.
Renee Weber (Neve Campbell) is a former girlfriend which Danny tricked in high-school, and she is obsessed with that still. I think Neve Campbell is playing badly in this movie. Her character is much less believable than the others. Jennifer (Rebecca Gayheart) is the most shallow character, I think it is not the actor as much as a problem with the script that makes her performance feel bad.
The progress of the film is fair enough. It starts with the background stuff, continues with a romantic sequence where the characters shows themselves, and sort of climaxes just before the end, after interference plots has played their part to affect the outcome of the film.
So, if you want to see a movie played well enough, at least as good as a standard TV-series, with a beginning and an end, with a romantic and somewhat complicated story which makes you feel good at the end - this movie should work for you.
I recently saw the 2002 version of The Count of Monte Cristo - a film where the filmmakers has destroyed a moderate story by making the last half of the movie a dull listing of on who (not even how) the Count takes his revenge (and of course a stupid happy ending), and saw that it has a 7.5/10 user rating.
This movie does not try to pretend to be much more than it is, and it certainly is a better movie than that movie. I don't feel like give it 7.5, but in its class I feel it deserves 6/10.