Lyric discussion by JaySayers21 

Cover art for Entertain The Pain lyrics by My Favorite Highway

this song to me is about a guy who cant get over an ex-girlfriend who left for some reason broke up with him and he didnt see it coming so now he's trying to cope with the whole thing but its taking him a long time to get over her. therefore he has to "entertain the pain" to make the bad not seem so bad.