I get that sometimes the world doesn't see things the way they are in our minds. Intentions aren't always the easiest to get across... but every woman at a party was trying to gently tell him how his actions might be interpreted, that's a pretty clear sign that he should've chosen to reflect on what he was doing. Even if he didn't heed their advice in the end, at least consider it.
I mean, had I been that girl... and been called upwards of 6 times in one night for something non-urgent like a party... I'd probably be thinking "What is wrong with this guy? I know one thing for sure, I won't be dating him."
Numerous lady friends over the years have tried to explain how obsessive behavior like that is not appropriate, and frankly can be scary. Especially to a girl who does not really know him, and wouldn't know any of us either. I think some women may start to give him the benefit of the doubt, or he simply behaves better when he meets someone, but by the time he has their number or method of person contact he's already on cloud 9 and completely convinced that she's the next big thing when this girl barely considers him a friend.
I think he just looks way into things, aside from women that is, and will get hurt or disappointed by them not turning out how he expected.
He really isn't a bad
guy, and no one really wants to break ties with him or anything like that. Buddy is the kind of guy you take in stride, and isn't exactly the kind of friend for everyone at times.But I wouldn't say he's malicious, more oblivious then anything. Perhaps a tad bit spoiled.
In relation to that comment about being spoiled;
Famously he had almost been kicked out of a friends apartment when he demanded soda to drink, and refused anything else she offered. A few friends had been over to her place and she was making popcorn, to which Buddy said he cannot eat it without soda. Friend has been working to drop some weight and as such she doesn't carry soda in her apartment. Her apartment complex does have multiple vending machines however. Friend offered Buddy that he was welcome to grab any drinks he wanted from her fridge including juices, and water but he refused and demanded soda. It got to the point where she finally told him; "You're welcome to any of my drinks, I have juice, water, etc.., or you can go get yourself a soda. Or you can leave"
According to another friend (second friend) who was witness at the time, Buddy just didn't have the change for the vending machine and was trying to fish for someone to offer him the money. Second Friend told Buddy later that if he had just asked him for the change, he would have given it to him. Instead he just had to have a fit about it to see if someone would drop a line on his whining. Literally, all he had to do was ask for the change and Second Friend would have had no problem giving it to him.
I think that whole thing is a bit like when attractive women know they're attractive but pretend to think they're ugly and make comments like "I wish I was as pretty as X" so someone will comment on them being pretty already. He wanted someone to take the bait so he wouldn't have to ask.
Malicious? No. Oblivious? Incredibly.
He isn't an inherently bad guy, just completely oblivious to his actions. His friends rope him in, and he has mellowed out considerably since I've known him.