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The girl who left him is now one of them wine snobs, so they must have broken up somewhere around 2011-2012. Which is strange because he then mentions her again in Seal Rock Hotel, which came out in 2013.
the guy she's with now is a serious downgrade in looks, but maybe an upgrade in money
Hard to imagine a downgrade in looks at this point.
How do you know it's the same girl? I can't see the connection from the lyrics.