Lyric discussion by EyesBehind 

"This evening I see you're about to get into / The ditch that your old man dug,"

I think, if we're going by the theme of naivite, this line alludes to the fact that the girl has come up in the world mostly on the shoulders of her parents. She is a Daddy's girl, and her reliance on him to get through the harder things in life will be the ditch she is about to "get into" once she starts her journey on life's road alone.

In other words, the ditch her old man dug was how much he was always there for her when maybe she needed to learn how to be there for herself.

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