It's a pretty simple song, about a pretty girl, from a place near Baltimore. Sometimes love hits you fast and hard, and sometimes it's gone just as quickly. Sometimes a relationship doesn't work out, sometimes it's a mistake, and sometimes you have to move on and learn from it, but that doesn't mean you can't look back fondly upon the good times you had...
"Pretty Girl From Annapolis" (grooveshark)
"And if I don't make it to the spring
May you catch the joy that a melody brings
From my dear brother's ragged six string...
...singin' the songs we're embarrassed to sing
may you never be embarrassed to sing..."
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