In this song about regret over a fading romance, the narrator watches airplanes take off, trying to figure out which one his former lover might be on.
Allan told Country Weekly magazine that he was close to calling the album Doing The Math: "That's always a weird thing for me. I always want to call it something that has nothing to do with anything. I almost called it 'Doing the Math,' from that 'Watching Airplanes' song [Checkin' my watch, doing the math in my head/Counting backwards to when you said goodbye]. I felt like Living Hard was the coolest looking on the shelf. That's where we're at right now. Everything's a little out of control right now. It's real heavy out there right now."
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