Cut for the TL;DR crowd
Let me come clean. I'm actually a nice guy, despite the voluminous intentionally blatant, over-the-top, licentious posts I make here. That's all for the yucks, even if I'm the only one yucking at the end of the day. I give help freely, I try and make people's days better, I generally think about other people's welfares before my own. I do have a dark sense of humor and can be that guy who walks over conservative people's moral sensibilities, but whatever. Overall, I try and be a decent human being. So, I usually don't hang around people who I consider to be overtly negative or destructive, if I can help it.
That being said.
There's not a great way to segue into this, so I'll start in the beginning.
One of my early friends was this guy named Chris. He was this golden boy back then. Everybody liked him; all the guys wanted to be his friend, all the girls had a crush on him, all the teachers wished more students could be like Chris. Even at the age of 10 or so, his charisma was exceptional. Around fifth grade, his dad was transfered to the midwest, and we didn't see him for a while. He came back when we were age 16 or so and promptly wooed and stole the girl I had a crush on. Like I said, the ladies loved him. That sort of soured our friendship and I didn't see him again, until a couple years ago.
In 2009, I attended this impromptu grade school reunion. My 8th grade class was very close back then, and considering how easy it is to find people on Facebook, someone decided it was a good time to gather all 34 of us (or however many had FBs), 20 years later. The event was...interesting. People had changed, had gotten married, gotten divorced, started families, the works. Like I said, Chris was there. He didn't graduate with us, but because he was so beloved by all, he was hunted down and invited to join. Chris is now what can best be described as a smug, self-important douchebag who hits on everything with tits. He made small talk with me, then went on to chat up Ivy and Michelle, a couple single mothers in my class, laying on this visibly creepy charm that was effective for some reason. He looks pretty damn good, I gotta say, after 20 years, rocking this stubbly, V-neck lothario look. Still, a douchebag. Afterwards, a few of us hit a bar, and Chris was at my table. He ignored his 'buddies' to whisper sweet nothings into Sylvia and Monique's ears, two more single moms. I exchanged looks with whoever I was sitting next to at the time, giving a "Get a load of this dick" eyebrow raise. He left early, not saying goodbye to me.
A couple weeks later, another former classmate and I grabbed drinks, and obviously we started talking about old times and what's going on now, and the subject of Chris came up, and we had a laugh about what a lecherous player he turned out to be.
Mind you, it's not jealousy. I'm not interested in dating anyone from my old class and I'm waaaay over that 16 year old girl.
Fast forward to an hour ago. Out of the blue, I get a text from Chris, asking if I want to hang out, get some drinks, etc. I'm not sure what I want to do here. If Chris seemed like a decent, somewhat grounded person, we could totally be friends, but I got this impression that all thinks about is getting some ass and I'm a little bit over playing wingman. Maybe I misjudged him. It's been like 20 years and I really don't know what the hell we have in common and maybe it'd be cool to catch up, but somehow I get the feeling that we'll be talking about his life and his adventures the whole time. We were childhood friends and maybe that counts for something, but on the other hand, I'm not really too interested in having a douchebag friend. I picture him losing interest in me mid-conversation as he starts to talk up the waitress who's collecting the glasses from our table.
So that's pretty much it. I don't know how to respond here. Should I hang out with my old pal Chris for drinks, and whatever adventures may follow? Should I not respond and decide that old associations don't necessarily validate future and existing associations if their conduct isn't to my liking? Will I hate myself more for not welcoming Chris back into my life, or will I hate myself more for welcoming him?
Sorry this is so long, but I figured details about my initial feelings and the back story may be relevant for your opinion