Situations have ended sad
Relationships have all been bad
Mine’ve been like Verlaine’s and Rimbaud
But there’s no way I can compare
All those scenes to this affair
Yer gonna make me lonesome when you go
~Bob Dylan (You’re Gonna Make Me Lonesome When You Go)

Much of the song is thus delivered, so lightly as to suggest that it’s in brackets, with the same sparkling, generous humour. Astonishing that a man who, by the time he made this album, had been monstrously famous for over a decade and had been acclaimed as a genius before he was 25, could have the down-to-earth self-knowledge to
throw out, in this song, so ordinarily humorous and puckish a phrase as the one that ends this stanza: ‘You’re gonna make me wonder what I’m doin’ / Stayin’ far behind without you / You’re gonna make me wonder what I’m sayin’— / You’re gonna make me give myself a good talkin’ to . . .’
~Michael Gray (The Bob Dylan Encyclopedia)

And how smoothly the album slips from this orgy of marital upchuck into the lightest, most innocent, most enticing love song of the whole batch, a throwaway which on closer inspection seems quite as brilliant (in composition and performance) as anything else here: “You’re Gonna Make Me Lonesome When You Go.” So clever, so perfect, to have a song that puts any separation squarely in the future, instead of present, near past, or distant past.
~Paul Williams (Bob Dylan: Performing Artist, Vol 2: The Middle Years 1974-1986)

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