We used to go on double dates, and he was one of these guys that always had mysteriously forgotten his wallet, so I had to pick up his tab. Then it was hell getting paid back. I'm pretty quick when it comes to these types of games, so I started making him show me his wallet before we'd go out. Then he resorted to what I call the "money swapping trick". I'm not exactly sure how it works, but basically, it's one of those deals where the waitress rings it all up on one check, and while you are trying to figure out who's stuff is what, he's going, "Umm.. ok, give me a $20, and then I'll give you this and that... no wait, give me this, and now I owe you that..." and before you know it, he's ended up with more money than he started with... But I recognized that crap right off and never fell for it. I started making sure the waitress brought us separate checks to avoid any more potential embarrassment.
This guy was the type of guy who had a perplexing self-destructive bent, always wrapped in a coating of humor... he'd take something perfectly good and just subconsciously screw it up, always landing himself into some hot water. I still remember the time he asked if he could rent my MR-2 Spyder for a date and offered me $150.00. My reply? "Hey, that's a great deal, Steve! So when you total my car, I get to keep the $150?"
Alas, our active friendship didn't survive much longer, because there's only so much one can take of feeling played. I don't think he was malicious at all -- just misguided, and that's just the only way he knew how to be. But he was also one of the FUNNIEST guys I'd ever met in my life. I still run into him every few years, and we crack up about the old days. I have so many hilarious stories about this dude....
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