Groupthink Advice Powers, ACTIVATE!

Hi. If you read this, just a warning, it will be long, but I am looking for advice.

(No mainpage, please)

First, a little history... I hate to admit it, but I am not a very good "people person." I am friendly enough, and, if you met me socially, we'd likely get along just fine. I love meeting new people, and interacting with others. It's just that I am notoriously bad at reading other people. It feels like I was born without a part of me that tells me what you are feeling. If you don't explicitly say, "I am happy," or "I am sad," or you are not actively smiling or frowning, I don't have the capacity to tell what you are feeling. I need it spelled out.

For example, let's visit my teen years... I was standard issue, chubby, yet gawky (don't ask me how I pulled that off), braces, glasses, weird 90's hair in high school. I had a few good friends, and that was good enough. One of them was "Sam," a friend of my brother. Sam was sort of goofy, but nice, and we hung out sometimes, mostly in a group, occasionally, just the two of us. Being a rather bookish, nerdy type, I figured boys would have no use for me, and I was fine with that.

Fast forward to a year ago, when I pulled out a box of old mementos from high school. In the box, was my cassette Walkman and a bunch of tapes. One was a mixed tape from Sam, that he had sent to me via the post, while I was at summer camp... 23 years ago... As a lark, I popped it in... And, I was stunned. As I listened, he interspersed his own commentary into the spaces between songs, and he was sweet, and funny, and sincere... And something else...

I called my brother. "Brother! Did you know that Sam was in love with me in high school?!"

Brother replied, "Ummm... yeah... Everyone knew that..."

"What?!? No one told me that! I never knew!"

"Well, then you are a moron, because everyone else knew..."

Yeah, that's the story of my life. Sam never explicitly looked me in the eye, and said, "Muffin, I'm in love with you. Let me take you away and make you the center of my world..."

I have no way of knowing how many times this has happened to me. Because, as I said, earlier, I don't have the ability to read what people feel...

Now, let's jump ahead in time to the present...

One of my friends is a guy, "Charlie." Not that unusual, I know. Our relationship is… complicated. We became friends at a super low point in his life, and I nursed him through some weird stuff. He knows I'm happily married, and he's friends with MuffinBoy, as well. Things were starting to go well for him. He's married, and has a bunch of family stuff going on. I thought he was happy, and things were going better. This is where the story gets weird.

He is very, very newly married. I think his wife just doesn't know what to make of me. I've been cordial, but she doesn't seem to want me around, which is fine. I get it. It's ok, really.

Charlie and I used to hang out a lot. We don't anymore. But, an event came up, across the state, and just for fun, I asked if he wanted to go with me. Charlie's wife was fine with it, and MuffinBoy was fine with it, so we made a plan. We left town in the afternoon, and hit the road. I always drive, so I handed Charlie my iPod, and said, "Ok, you DJ." Back when we hung out, we would drive around, and he'd play music, so it was sort of an inside joke.

He got very quiet and poked around at it for a long time until I asked what he was doing and he replied that he was making a playlist. He put it on, and we started talking, with the music in the background, and an hour and a half later we reached our destination. We had dinner, walked around the city, saw a show, and headed back home. We said goodnight in my driveway, and he drove away. No big deal.

A few days later, I pulled out my iPod, and put on "Charlie's Playlist" for fun. Whoa. Every song was about falling in love, missed chances, missing your one, true love, longing for a new start, etc., etc. It was weird. My iPod has over 3,000 songs. You think he'd be able to pick something that wasn't about love, in some way or another.

So, if you've read this far, what do you think? Am I hyper sensitive because of the incident in high school? Am I reading way too much into this? Should I say something? If so, what?

I know I've given you very little detail on our friendship, but I could write a book on that alone. I can't talk to anyone IRL about this because we have a circle of friends, and we all have friends in common, and I'd hate to have anyone take this back to his wife… So, Groupthink, am I nuts, or is this something I should talk to him about?