Lyric discussion by VampedVixen 

Cover art for The Babysitter's Here lyrics by Dar Williams

I'm torn. In one way I can see what Desaparecida is saying, though I have another idea. That the babysitter, though liberal, loved being innocent and babysitting with children. Her boyfriend wants her to go to college, to become one of the liberal free women that aren't little housewives. Though she really wants that old style wife's life she is so swept up by the woman's movement that she does what is supposed to be right and chooses freedom even though she still wants a family life instead.

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...