This song records the kind of vapid conversation, disguised as witty repartee, that occurs at cocktail parties.
It starts with a man realizing he is being, as they say, "checked out" by another party-goer. He can tell by her assessment that she is only approaching him because he is one of the least unappealing people in a roomful of people with limited appeal altogether. He uses the shrugging words "guess," "thought," "all right," "limited" and "off-night."
This is hardly the response, say, the Caribbean Queen has to the speaker of the Billy Ocean song of that name at another get-together: "She said I was the tiger she wanted to tame."
The woman in question here, seeing no tigers worth taming, opts for our speaker and leads with a version of, "Haven't I met you someplace before?" In her case, it's the more sophisticated version: "Don’t I know you from the cinematographer’s party?" (A "cinematographer" being someone expert in the technical aspects of film-making, possibly also with an eye toward their artistic possibilities).
Now, our speaker may or may not know a cinematographer. He may or may not have been to this party, and he may or may not have met this woman there. Even if he did, he may or may not remember her. But he can't tell her this. And anyway, it doesn't matter-- she knows him now.
If I say "no," he thinks, the conversation is over. But I can't give a definite "yes," either. So he obfuscates. He says something like, "Sure, why not just say so, if it means we can talk?" But in this case he opts for the more poetic, more off-handed, "Who am I to blow against the wind?"
The woman knows this is an obfuscation, so she sets him up by insulting him somewhat, and vaguely: "There’s something about you/ That really reminds me of money." Now, there is no way this a good thing, but he is unsure in which way she means it as a bad thing! Does she mean he is materialistic? Opportunistic? Elitist? He knows he is being insulted, and so thinks: "She is the kind of girl who could say things/ That weren't that funny." But he doesn't know how he is being insulted.
Trapped, he has no choice but to ask for clarification: "What does that mean..?" To which she shoots his own line back at him: "Who am I to blow against the wind?" now meaning both, "Hey, that's the way it is, I can't control how I feel about you," but also, "How does your own medicine taste, mister?"
He is stung, but impressed at her wit. Also, she seems very lithe: "She moved so easily/ All I could think of was sunlight." (And isn't that a beautiful line!) But he can't say anything that overtly sensual at this point. So instead he compliments her intelligence, asking “Aren't you the woman/ Who was recently given a Fulbright?”
A Fulbright scholarship is an extremely prestigious honor. It means that you are so excellent in your field, so innovative, that you are being sent by a Presidential panel to study and teach at a key institution or research station somewhere in the world. It is like being a Rhodes scholar.
She brushes off the question, responding that she is sure she knows him from that other party. He still refuses to answer her directly with either, "Yes, in fact, and I'm glad to have run into you again," or "Actually, no, but I'm glad I met you now." He replies again with, "Who am I to blow against the wind?"
The chorus is much more straightforward than all of this bandying about, but it gives a clue to this hesitancy and around-the-bush verbal dance the speaker is doing. He is certain of something-- that all things end.
Decades after the closing verse of "Leaves That Are Green" was written, Simon is still saying "Hello, hello.../ Goodbye, goodbye.../ That's all there is." Only here, he says it more succinctly: "We come and we go."
Life ends. Relationships end. There will be a "goodbye," a "go"-ing, no matter what. So the "hello" had better be worth it. If I am going to spend some of my limited time on Earth with you, he implies, I want it to be something that has a long and good time until the "goodbye."
On the one hand, she is attractive, or at least graceful. And she's not entirely unintelligent, as she did sting him back with his own barbed comment.
But there is something unattractive about being someone's "you'll do." ("Weird" Al Yankovic has a very funny song about this called "Good Enough for Now.") Read the opening lines again-- she doesn't truly want him, and will leave as soon as someone better shows up. Wouldn't it be better if he treated her fairly coldly and she just left him now, before the heartbreak and break-up?
The comment about her receiving a Fulbright wasn't a compliment-- it was a test. Of course she didn't receive a Fulbright; she doesn't even know what one is. When she doesn't answer directly, he thinks, "...Aaaand that's what I thought." Now he doesn't have to feel bad about not being good enough for her looks-wise... because she's not good enough for him brains-wise.
At all times, "in the back of [his] head," he remembers that things end. It's a good thing to keep in mind, because it stops him from beginning things that have the seed of their end before they even start.
And so he should only start up with people who are worth his time. Maybe he'll find one at the next cocktail party.
Next song: Gumboots