It's impossible to analyze this film without breaking it down into its four segments for separate comment. It would also be improper, since it was not intended to be anything less than an anthology from four notable independent filmmakers: Alexandre Rockwell, Alison Anders, Robert Rodriguez, and Quentin Tarantino.
The first episode is exactly the sort of thing that someone in a high school drama production would want to do, but can't get away with in a high school drama production. It's juvenile, unfunny, and lifeless, but it has the (pointless) nudity that sound like the screenwriter is giggling and thinking, "I can't believe I'm getting away with this! I'm so clever!"
Nothing is at stake in the first episode; it's generally expected that a story must have conflict in order to BE a story. This has none. Just some half-baked jokes and a pair of topless women (If I wanted that, I'd skip renting a movie and go out instead.)