Far, far away by Wilco. The verse about the "Kiss & ride on the CTA" always grabs me.

Tonight, Tonight by the Smashing Pumpkins because of the line "City by the Lake..."

 

And Tenderness by General Public. That song was playing the first time I drove my college girlfriend home. The joke was I turn right when Tenderness comes on. Pretty funny, huh? Anyway, everytime that song comes on, that right turn pops into my head at Manhattan-Monee Rd and the road with the light post on the northeast corner.

I was the biggest jerk in the world. While she was planning a romantic 3 year anniversary weekend for us, I was planning on breaking up with her and had already lined up a date with this really hot girl from one of my classes. We wound up going out for 2 years, 11 months, 3 weeks, and 5 days.

 

The only redeeming value, the only shred of decency or karma, is I married the woman I dumped her for.

 

To this day I cannot believe that was me being so mean an insensitive. Of course back then I was in the Young Republicans, I guess they rubbed off on me.

 

That sucks...but yeah...I got ya beat.

 

Dating a girl for a spell. She had some mental problems that she took meds for. She was fine on the meds. But then it came break up time. She showed up on my porch, told me she was back in group meetings, stopped her meds...yadda yadda. I looked her dead in the eyes, said:

 

"Don't hand me any of this suicide, back on drugs bulls*** just because we broke up. I personally don't f***ing care anymore, just get out of my f***ing life" and shut the door on her.

 

I ran into her a few years later. Things were going pretty good for her. So hey, it all turned out O.K. I guess. I was young, stupid, and UNBELIEVABLY mean. My wife, through the years, has heard a few stories from my teen years, and she is shocked by most of them, and hates hearing them. She has said on more than one occasion that she would never have dated me if I was anything like I was then.

 

Little signs show up now and then though. But we all did dumb things during our "dating process" while teens.