In college I had this friend who always had to know what everyone was doing. I wouldn't say he was gossipy, since I don't think he used the information to talk about them behind their back or anything, and gossipy sounds sort of fruity, so let's just call him overinterested.
I found this sort of annoying. I'd be telling a story and he'd interrupt a dozen times wanting to know who I was with while I was trying to get to the meat of the story. After a while I found a way to turn this annoyance into a amusing little pasttime. By simply dropping a little information, I could entertain myself for about a half hour or so. I'd start out simple.
"I went to the movies with ...ah, you know, that one guy and the girl? Anyway, it was pretty cool."
"Was it Dave?"
"No, no, it was..you know, that one dude. Anyway, Bruce Willis is running in front of this big fireball, then he turns and says, 'hot enough for you,' and -"
"So was it Jenn? Julie?"
"No, you know, that girl with the hair that hangs out with that guy? Anyway, so Bruce Willis throws a spear at the main terrorist and says, 'stick around,' cause he stabbed him with a big spear -"
"Did you go with Scott? Casey?"
"No, no, no. So then the terrorist pulls out this uzi and is all like, 'eheheheheheheh' and Bruce Willis pulls out his gun and is all like 'gushgushgush' and -"
"Was it Jimmy? Todd?"
"Nah, it was, you know, that one dude and the girl. Anyway, so Bruce Willis is all like 'gushgushgush' and ..."
By this time the guy's face would be turning red as he practically recited the Gainesville phone book to determine who I went to the movies with. If I was feeling especially sporting, I could drag this out to a half hour or so. Awesome thing is, he'd fall for it every time.