After taking some of your suggestions I decided to write a couple blog posts on what my songs are about and where I got the inspiration to write them. The best story I have any probably the most asked about is none other than "Lipstick Lesbian". Oh Lipstick Lesbian. This song has always gotten me in trouble with girlfriends because it's all about me chasing "the one", however that "one" is obviously not the girlfriend at the time, since not many girls fit the description in this song.
Here's the story (the semi-short version).
I went to college at the Naval Academy, where I sang in an all mens chorus (awesome group by the way). We often took trips and in 2004 we ventured up to Smith College in Massachusetts, a school known for over half of the student body being lesbian or bi-sexual. No problem. Turns out they party like rockstars and we got along great. While drinking, singing and carrying on at Smith I met a girl named Nicole who invited me to a party that night. After telling a few of my friends about this one of them came back and said, "Dave, you know she's got a girlfriend, right?" This is where it all got interesting. I hung out with Nicole at the party, but not too much, the weekend passed and a few months later the vixens from Smith college came to visit us at Annapolis. This time we ended up drinking and singing together in a hotel room with about 20 people, and it was then I realized Nicole and I had a lot in common. First off, she had a killer voice, which with me means she takes the expressway to my heart, second, she was a fun girl who partied hard and had the looks to boot (hopefully this isn't starting to sound like some kind of cheesy romance novel). We hit it off, I got one kiss, and we parted ways.
Bummer.
This however made me think a lot about this girl and a few months later I picked up my pen and wrote "Lipstick Lesbian", a song all about how I tried to woo a girl who had a girlfriend. If you listen to the song you'll hear a middle part about her girlfriend beating me up, which (I'm happy to say) I made up. Her girlfriend was butch though, and I know for a fact I was near the top of "guys I would love to strangle" list, thanks to my interaction and subsequent song about her girlfriend.
As a follow up story, I recorded the song in October 2004 and sent it to her at Smith. When we returned to sing with Smith again in 2005 I was pretty surprised at the amount of people who had heard the song, it was really really cool having people come up to me saying, "hey, you're the lipstick lesbian guy!"
(some more good times happened that weekend but I know my Mom reads this so they won't be mentioned… just email me)