This movie really wanted to be thought-provoking and interesting, the kind of bittersweet film that finds some good in the sleaziest of characters, but instead, it was a glimpse into the world of a largely despicable guy with very little payoff. The premise is that this guy Roger, a know-it-all, self-absorbed, and rather pathetic jerk, is helping his nephew Nick get laid. And in the process, pontificating about how the world works, how women work, etc. Roger spends most of the movie expostulating these theories, and nobody really buys into them - even Nick, desperate though he is for advice. Unfortunately, the viewer of the film has to sit through a lot of them anyhow, and the entertainment value wears off very quickly.
The movie, I think, is trying to redeem Roger. It seems geared towards having Roger realize what a prick he is as a result of his interactions with Nick. And yes, Roger does ultimately burst in and stop Nick from having sex with a prostitute (after he's dragged him in and payed his way), and yes he makes Nick call home. And in the final scene, where Roger visits Nick at school, and attempts to educate the lunchroom crowd of geeky guys in the art of seduction, his theories have been somewhat adapted. But there's no evidence that he has genuinely been converted out of his objectifying, crude views on human relationships - quite the opposite. It's just that he's realized that high school is actually less of a meat market than your average New York bar, and the rules are somewhat different. Roger is just as much of an asshole as he was in the beginning of the movie, and he's still not a likeable guy. The fact that he's been jilted by his mistress (who is, of course, older, richer, and more successful, and is well played by Isabella Rosellini) doesn't make him more sympathetic, it makes him pathetic. Of course she's dumped him. Why would she condescend to sleep with him in the first place? I respect the fact that the makers didn't want to have a fill conversion über happy ending. I appreciate it even. But they also don't seem satisfied to leave him be as a complete dirtbag. And honestly, I don't want to spend 2 hours with a complete dirtbag. So something's gotta give. At some point, I need to be convinced that the movie is aware of the fact that Roger is full of shit.
One could make the argument that Nick's more romantic notions serve precisely to disprove Roger. But Nick's voice is obviously so much weaker, and at best, he can not take advantage of the opportunities for despicable behavior that Roger affords him. But ultimately, it's Roger who saves him from degradation - he can't do it himself.
Also, the movie suffers from over-the-top theatricality. It's totally artificial. The middle section of the movie, where Nick and Roger chat up two women in a bar, and then in a park (the two women being played, rather gleefully, by Elizabeth Berkley and Jennifer Beals) is completely preposterous. It's that spontaneous, super honest, "genuine" kind of interaction that does happen sometimes in life, but is far too convenient here. The scene where Jennifer Beals is riding away in the taxi, and the expression on her face suddenly changes from playful musing to acute melancholy, is just irritating. Oh, how very profound. The mysterious inner lives of random strangers have suddenly been illuminated. Please.
Ultimately, your feelings about the movie will depend entirely on whether you find the main character, Roger, completely worthless or not. I know there are people like Roger in the world, but honestly, I'd like to believe they have moments where they're not total scum. Not that I want to see the revealed as just like everybody else, but I would be more interested in seeing them rendered more complex, rather than placed on a pedestal and given the air-time they so desperately crave. To be fair, I find Campbell Scott ungodly annoying, and this probably has more bearing on my assesment of the film than it ought to. The guy just irritates me. And it's not the kind of "love to hate him" feeling, I just don't think he's worth my time. And thus, neither was the movie.