Lyric discussion by IslandMyk 

To add to iluomo's entry...I think the song's about a couple of friends who used to be wild and free, but one of them got married, had some kids, and found herself kind of stuck in Alaska as a housewife while the other is still out there, living the musician's life.

Sounds like Leroy might be a little overbearing, since it seems like she can't even write a letter to an old friend without him butting in and adding his two cents.

So, maybe the song is about the peril of settling down at the expense of your dreams.

@IslandMyk You are projecting that on to poor Leroy. She probably said, "Hey Leroy! Guess who sent us a letter? Michelle!" And Leroy replied, "Oh, cool. Tell her that I said hello!"

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