This song is called "Sad Eyes" and it's by Josh Rouse (probably the most underrated musician I follow) from his 2005 album NASHVILLE. This album is one of my favorites, likely in my top 10. I was happy to have Sad Eyes playing in my head today. The breakdown at about 3 minutes into this song gets me every time.
In the simplest way, the song is about somebody trying to cheer another person up. It's sweet, simple and just lovely. Have I mentioned I love this song?
Not much else to say folks. Thanks for reading/listening.