You're with a loser.
Are you one too? Why don't you
Come date me instead.
If Dylan's worst qualities, lyrically speaking, in the late 1970s and early 1980s were his sour moralizing and his toxic blend of self pity and anger toward women, his worst quality at the height of his fame in 1965 and 1966 was an arrogance born from intelligence and the irritation of others that seemed to shoot in all directions.
"Can You Please Crawl Out Your Window" is the tale of Romeo seducing Juliet from the window, but by mocking her even as he makes clear that he has lustful thoughts on his mind. Toward the woman he's singing to, you hear petulant demands and scorn.
Can you please crawl out your window? Use your arms and legs it won’t ruin you How can you say he will haunt you? You can go back to him any time you want to.
The man she's dating, meanwhile, takes up each of the song's venomous verses. Example:
He looks so truthful, is this how he feels Trying to peel the moon and expose it With his businesslike anger and his bloodhounds that kneel If he needs a third eye he just grows it He just needs you to talk or to hand him his chalk Or pick it up after he throws it
Dylan can't even talk to him. He just harangues her about him. It's great to be young, smart, wanted and admired, but you get the impression that for a year or two, the singer couldn't stand to be around anyone because they're all a bunch of assholes. But there's a saying about the company that you keep...
I don't enjoy speaking this way about people I don't know, but the temptation through a song like this becomes too strong. It seems clear that the eventual motorcycle accident and decision to hop off the grid and into upstate New York was just what the man needed. I'm sure that he's even crustier today, but wisdom, if it comes, has a tendency to blunt arrogance, even if it can't cure misanthropy. Separately, I read on Wikipedia that when Phil Ochs and Dylan were riding in a limousine together, Dylan played the song to him. When Ochs was less than impressed, Dylan reportedly kicked him out of the limousine, shouting, "You're not a folk singer, you're a journalist!" So. There you go.
The song was released as a single in 1965 and is available on the "Biograph" anthology from 1985. I can't get a Dylan version to load up so I'm sharing Roger Daltrey's.