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SO REMEMBER THOSE WHO WIN THE GAME
LOSE THE LOVE THEY SOUGHT TO GAIN
IN DEBENTURES OF QUALITY AND DUBIOUS INTEGRITY
THEIR SMALL-TOWN EYES WILL GAPE AT YOU
IN DULL SURPRISE WHEN PAYMENT DUE
EXCEEDS ACCOUNTS RECEIVED AT SEVENTEEN
These are lyrics from a Janis Ian song "at seventeen"; could you please help me understand what's in bold?

PS: shouldn't it be "when payment'S due"?

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Comments  (Page 3) 
Hello, I have also always wondered about the "debentures" part in the song. My interpretation is a bit different, I think the song has an ironic twist in this verse:

"Remember those who win the game will lose the love they thought they gained."

This obviously refers to the "beauty queens" who "married young": So even though they were the popular stars "at seventeen" they won't be happy (with their husbands) for long, for they will lose their love.

"In debentures of quality and dubious integrity"

I'm still not sure about the "debentures" but the "dubious integrity" refers to their marriages, which are not as happy or secure as they might seem.

"Their small-town eyes will gape at you in dull surprise when payment due exceeds accounts received at seventeen."

This means, that later (when their marriages have gone stale) they pay the price for the happiness in their youth; and this price is too high, it more than outweighs the happiness / popularity when they were seventeen.

So basically this appears to mean, that the "ugly ducklings" and "brown-eyed girls in hand-me-downs" have the last laugh so to speak.

Can you follow this interpretation? I am not a native speaker, so I'm not sure if it really comes across.

Bye

Purschka
I think it's supposed to represent that "those who win the game" had it so easy that they never had to rely on anything but their looks. And if they were aware of this fact in high school they might have been rather nasty to the kids who weren't "pretty" or "handsome".

So as they go out into the real world, those who "won the game" of popularity in high school perhaps have no real skills beyond that. Thus the debentures of quality and the dubious integrity--and when this reality sinks in, then their "small town eyes" will "gape" at those who have quality and integrity (the "odd kids"). And the "accounts received" and "payment due" signals that they are ill-equipped to go forward when the reality surfaces that "just being pretty" isn't enough anymore--and they're shocked by this realization.

Just a guess...
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another question based up on the same lyric song... what is the metaphoric for... "A BROWN EYED GIRL IN HAND ME DOWNS
WHOSE NAME I NEVER COULD PRONOUNCE
SAID -.... thank you ...
The verse is actually two very long sentences.

SO REMEMBER THOSE WHO WIN THE GAME LOSE THE LOVE THEY SOUGHT TO GAIN IN DEBENTURES OF QUALITY AND DUBIOUS INTEGRITY

THEIR SMALL-TOWN EYES WILL GAPE AT YOU IN DULL SURPRISE WHEN PAYMENT DUE EXCEEDS ACCOUNTS RECEIVED AT SEVENTEEN
You need to read the whole phrase as one statement. It's about young girls (17) trying to get the guys they desire by playing "games of attraction." Sometimes they win (Remember those who win the game), sometimes he goes along just for sex (lose the love they sought to gain). and sometimes he's not worth it (In debentures of [lacking] quality and dubious integrity). Yet there is a price for winning, which surprises the inexperienced girls (Their small town eyes will gape at you in Dull surprise when payment due) -- and they have to have sex when all they wanted was to be loved (Exceeds accounts received).
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I think it could be interpreted as this: looking at the the people who "lose the love they sought to gain" they lost the love like a gambler loses money; they gamble it and end up losing it due to debts. So the people the singer is referring to have lost the love they sought to gain by gambling it in dodgy "loans" (taking a leap of faith etc) and we know they're dodgy from the line "dubious integrity." "Their small town eyes will gape at you" could be referring to how friends and family take the outcome of the debenture (which probably ended badly) however they're not surprised at the outcome (dull surprise) as they knew it was a dodgy deal/trust thing. (Dubious integrity again.) Then "exceeds accounts received" could be inferring how bad relationships often leave you worse off than before. Think of it netaohorically as a gambler with an addiction who gets into a financial mess. The lover is the gambler, the love is the winnings, the loans to pay for gambling is the debenture of dubious integrity and the financial mess is the heartache in the aftermath.
Here's my take on this...

Remember the "pretty people" in high school? They seemed to be winners at "playing the game", but they were shallow, and sought love in equally shallow people who lacked quality and integrity. Then, in the end, often years later, they were surprised when they discovered that the costs associated with pairing up with such people outweighed the benefits.

So remember those who win the game
Lose the love they sought to gain
In debentures of quality and dubious integrity
Their small-town eyes will gape at you
In dull surprise when payment due
Exceeds accounts received at seventeen


In my opinion, this doesn't refer to the beauty queen later in life regretting the choices she made during high school. It's more of an instant karma. She flirts and gets the handsome football star, intending to ride off into the sunset with him and live happily every after. But Prince charming doesn't want to love her, he wants to have sex with her. The relationship is shallow, lacking quality and of dubious integrity. She's taken aback when she realizes that she's putting out (payments due) but not receiving the love she sought (accounts received). This realization occurs not in the far off future - but at seventeen. Hence the last two words.

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I believe that only in the UK are debentures secured loans while in the US, they are unsecured loans, which makes more sense to me.

Hence, if one receives an unsecured loan of quality lifestyle due to relations/status and then cannot live up to the expectation, they have exceeded all goodwill they have (accounts received).