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Dar Williams – The Babysitter's Here Lyrics 12 years ago
I think you've got it turned around. Tom doesn't want her to go to college--if she chooses school, he won't marry her. She asks Dar/the child not to "go with a guy who will make you choose", which suggests that the babysitter wants both school *and* Tom/marriage. Tom is the obstacle.

For me, there are two ways of seeing this song, and both are interesting although one is less universal than the other.

One: Choices in relationships, and what love means. If Tom loved her, he would encourage her to go to school and not force a choice between "love" and education/self-improvement. This would be an easy decision for me--I'd tell Tom to stuff it--but I'm 20 years older than the babysitter and decisions like this seem less dire when you're well into your thirties in the 2010's than they must have when you were a young girl in the early 1970's.

Two: Women in the "liberated" 1970's. For all the talk of love and freedom and equality, the hippie movement often didn't do very well by minorities and women. Tom is at least a wannabe radical who wears a flag on his pants, but he still expects his girlfriend to do as he says and give up her own aspirations for him.

I always like this song much better than I expect to. It seems as if it will be a cutesy song about a kid and her favorite babysitter, but then it gets complex and kind of dark, but without becoming pretentious. The lyrics are amazingly economical: It tells the listener a lot with only a few words.

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Alison Krauss – The Lucky One Lyrics 12 years ago
This isn't about envy. She's been hurt, yes, but she doesn't want his "luck". He's "lucky" because he's skating through life on charm and superficial relationships but he's not engaging in anything substantial ("the next best thing to playing and winning is playing and losing". He's about playing; he doesn't care about the outcome one way or the other).

The lyrics are sarcastic--"so I've been told", "jack of all trades, master of none". "You're the lucky one, I know that now" is about figuring out who he really is and wishing a bit that she were as indifferent to him as he is to her, to spare herself the sting of a reality check, but she doesn't really want to be like him.

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