I'm gonna start with Vanessa, because this song was the one that gave me this idea.
I first came across Vanessa around 2002, I think, when I used to post on the Aimee Mann message board. We bonded over a Fiona Apple song called Never Is A Promise, specifically the "live on KCRW" version of the track (which I absolutely adore). You can find it on Volume 3 of KCRW's Rare on Air series, if you want to look for it.
Things around the message board got kinda weird, so I deleted all of my posts and decided to just live on the now-defunct Bowlie forum. I didn't feel particularly attached to the Aimee Mann community, and I spent way more time at Bowlie, anyways. Vanessa was the only person (on the Aimee board) I really liked, so I told her I was gonna bail, sent a Bowlie link to her and asked her to come along. To my surprise, she did and everything turned out pretty cool. We got to hang out more than a few times and we became pretty good friends. I'm fairly sure the pic above is from a Bowlie meet in New York in 2003. If it wasn't for this Fiona Apple track, we might not have chatted much at all.
Fiona Apple > Never Is A Promise (live KCRW)