do rather well with the subject matter- albeit limited, and as a previous review mentioned, ("Pretty In Pink, Redux")...sometimes there is fault with pop culture trying to seem clever; just ask Stephen King.
Ringwald is a decent actor, and was unfortunately pegged into these type roles for awhile- I will have to watch her later films to compare, as it seem she has not been given enough range. Since this film was made in the late 80's; there needs to be a twist; Andrew McCarthy provides a sympathetic character-trying to do the right thing. (Was there a "right thing" in 1988?). I seem to remember films like "American Psycho" reflecting , more accurately, the political and social climate of the times.
What the audience does see, is interesting and expository. For example; why do the Ben Stiller and McCarthy character have to visit their college girlfriends at their indoor/outdoor swimming pool?; this is a gross exaggeration. Unless their parents owned a software company; being well-to-do does not necessitate an Olympic sized/Mariott Hotel swimming pool.(Wow-the parents went to St. Martin-not exactly a world cruise). But, yes, this is the 80's. So we will excuse that. I can remember films like "Soul Man" (1989) and "Who's That Girl" (Madonna- throw-away trash film) The Ringwald character could have been better developed, she is a townie; married too young; the speech when she explains her childhood could have been more nuanced, more true to life. Ben Stiller is realistic, except when he delivers the title phrase to McCarthy- ..."drop the old nag and get a new one"... when referring to Jewel(Ringwald). Also the final deus ex machina- where Ringwald is assaulted, yet stays with Green (Viggo Mortenson) is contrived and convenient. Andrew McCarthy is a good actor, without the luxury of a story-line.
In the late 80's, there were some films with social merit. This was one of them, but you may have to block out some of the more ridiculous polarizations. The fact is that there will always be college, college preppies, and townies, who drive 1979 Camaros. The writer must show the audience why we should care, and learn about the many conflicts and psychological issues.