Lyric discussion by phomer 

I have been the girl (well, I'm a guy but you get the point) in this song in real life.

I once left a girlfriend behind at home to travel through South America. I told her I'd be away for six months, but once I got there I realized I needed more time. So I wrote to her and told her my trip would be more like eight months.

Her response, though she had never listened to Dylan, was pretty much exactly what Bob writes in the penultimate verse. My thoughts were not with her. I went home after eight months but things were never the same and we soon parted ways for good. Every time I hear this song now, I cry for the guilt of how I broke her heart, how lonely and abandoned she must have felt at home, how the emails and letters and gifts I sent her to "make her time more easy passin'" were really, at the end of the day, worthless.

@phomer - - - that is quite a story. when you say you sent her gifts, of course it calls to mind these boots. i wonder if you ever had occasion to later tell her this full tale

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