Last Friday’s Matt Nathanson-themed Power Ballad post has got me flashing back to my introduction to his music — which, unsurprisingly, coincided with my introduction to one of the Girls in My Life.

It was the fall of 1999 when I met Good Nicole (thus named to provide distinction from Bad Nichole, who you’ll meet later), and in retrospect, dating her was probably not a very good idea. I was in the middle of a strange period: Running my label, recording my solo album, and dealing with the terrible consequences of hiring an ex-girlfriend (also to be introduced later) as my publicist. During the six months or so that we dated, I’m not sure Good Nicole and I were in the same time zone for more than a week at a time; during one particularly busy stretch, I went from the Bay Area to San Diego to Hawaii to Cleveland and back again.

Still, even if someone was bound to get burned, we had some good times while it lasted. During one of our earliest conversations, when she found out I had a “career” in “music,” she suggested that I check out her favorite unsigned artist (you guessed it, Matt Nathanson). I dutifully ordered up a few of his CDs and was sufficiently impressed to make plans for us to attend a Nathanson gig the next weekend.

As I said, it was a weird time in my life — one I have fond memories of, and even if those reasons don’t ultimately have a lot to do with Nicole, she’s still part of the happy swirl I flash back to when I hear Nathanson’s “Loud” (download). (Which is sort of ironic, given that “Loud” isn’t remotely a happy song, but whatever.) Hearing “Far & Wide” (download), the opening track on my solo album, has the same effect.

None of it was meant to last — not the label, not the music, and not Good Nicole. By the following spring, we were kaput, after weeks of callous disregard on my part that I told myself was schedule-induced but, looking back, had more to do with the selfish boredom of a twentysomething idiot with too much access to too many unimportant things. I still flinch a little when I think about the way I acted back then, but we’ve both obviously moved on to better things, so all’s well that ends well, right?

I think most of us, at one point or another, have carried an unrequited torch for someone. Mine happened to last, off and on, for about five years, meaning that any ongoing discussion of music as it relates to the girls in my life will periodically turn to Jill, and in the interest of spreading those stories out a little, we might as well get the first one started now.

As I mentioned, this was a totally one-sided relationship, at least as far as anything more than friendship was concerned. This became clearer to me over time, but at sixteen, it’s sometimes difficult to tell the difference between a girl who’s sending mixed signals and one who’s just trying to be polite. When my daughter is old enough to care about these things, one of the first things I think I’ll tell her is that it’s more important to be completely honest than it is to try and save someone’s feelings — you never know when, for instance, your actions will be so grossly misinterpreted that they lead the person in question to, I don’t know, drive halfway across the country to visit you. Unannounced.

That’s another story, though. When I hear Jude Cole’s “Hallowed Ground” (download), I think about the spring of 1990, when Jill’s family moved from the Bay Area to Colorado, which happened to be around the same time I realized I still had feelings for her, and had made a huge mistake by getting involved with someone else who just happened to be one of Jill’s best friends. (Again, another story.)

It’s kind of a corny song, yes, but I think it’s easy to see how it might appeal to a melodramatic teenage wiener — and even now, those beds of acoustic guitars sound good to me, and the line “I was your trouble and you were my friend” still rings true.