The song is about a guy that always "picks the wrong girl". He comes into the bar again and again ALONE because he always ends up that way. She is a bartender and watched him again and again doing this to himself over and over (in the video). She says "You are drinking whiskey when you should be drinking wine" Meaning you are killing pain when the pain shouldn't be there in the first place. People often drink whiskey to kill pain and wine to celebrate or romantically. That is a cliche in all country/bluegrass music. She is saying stop wasting your love and time on "fly by night cowgirls" that keep bringing you down and give me a try for something real.
The song is about a guy that always "picks the wrong girl". He comes into the bar again and again ALONE because he always ends up that way. She is a bartender and watched him again and again doing this to himself over and over (in the video). She says "You are drinking whiskey when you should be drinking wine" Meaning you are killing pain when the pain shouldn't be there in the first place. People often drink whiskey to kill pain and wine to celebrate or romantically. That is a cliche in all country/bluegrass music. She is saying stop wasting your love and time on "fly by night cowgirls" that keep bringing you down and give me a try for something real.