In order to properly tell this story, we have to go back in time. Way back. The year was 1996. People thought pagers were a great communication tool, Bill Clinton was in the White House, Britney was still innocent and I was a junior in high school.

I mentioned in my 100 things list that I was a choir nerd during high school. That meant concert choir, jazz choir and a variety of small singing groups. I spent a lot of time performing. I don’t know that I was any good, but I did enjoy it. Unfortunately choir didn’t offer was a wide selection of cute boys to look at. At this point in my life I was pretty boy crazy so it was definitely a disappointment.

At our fall concert, I was assigned to keep the junior high choir kids in check while they weren’t on stage. My partners in crime were my best friend, the jerky guy that she liked at the time and his friend, TTO. When you grow up in a small town you know most of your classmates from birth. I knew of TTO, but I didn’t actually know him. After laughing and joking around (and getting in trouble for not doing our job) I was pretty smitten.

All I could think was, “Why didn’t I notice him before? He’s pretty cute.” We spent the next week or two walking the halls after school talking. I baked him cake to prove my domestic prowess. My friends referred to this as “just being casual”. Finally, after one of his basketball games, TTO asked if I wanted to go out (did anyone else use this term? My aunt used to HATE it – she always asked “Where exactly do you GO?”).

Our relationship consisted mainly of me wearing his class ring, phone conversations and a lot of innocent making out. One incident I remember in particular involved me driving him home from a dance with my two best friends in the backseat. As I was pulling into the driveway D said, “Maybe you should walk him to the do..” She was cut off by our gratuitous kissing. I never quite lived that down.

I also met his mom for the first time when I was stocking shelves in the feminine hygiene aisle for my drugstore job. That was fun.

One night during a phone conversation about a month later I told TTO I couldn’t be his girlfriend anymore. He went silent, then said “I’ve got to go.” I’m still not sure why I did it. None of my friends had boyfriends so I think that was part of it, but I also wasn’t that good with relationships. I was too non-committal. When he missed school the next day I felt awful – he had a perfect attendance record and I’d ruined it. I tried to stay friends with him. I even convinced my best friend to ask him to prom (she did and it was extremely awkward for all of us).

Eventually we just stayed clear of each other. He dropped out of choir to pursue other things and I graduated and moved away for school. I thought of him every once in a while in a very “what if” kind of way. I never would have guessed at what was ahead.

*All of the posts this week will have John Mayer songs for titles.  Say what you will about him, but whenever I hear his songs I think of TTO and the early days of our relationship.