I'm resigned to sail on through
In the wake of tales of you

from Fiona Apple – Valentine Lyrics on Rap Genius


She describes her destiny with a sailing metaphor. She believes she is can do nothing but to sail down the street in the wake of her beloved, always stuck behind him.

Additionally, because boat wake is turbulent, we can assume that the “tales” she’s hearing about her lover are stories of new girlfriends and happiness that he’s experiencing, which in turn cause her emotional turmoil.

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