Celine Dion "The Last to Know"

Dating off a radio station's request line is never a good idea, but that never stopped a creepy older gentleman named Jack who made the request line his personal Match.com. In this case, the 25th caller to the radio station whenever one of Celine's songs played would win tickets to see her in concert. For the folks who weren't caller 25, they won the consolation prize: a conversation with Jack. Jack would flirt with them and actually set up "dates" with some of these women by inviting them to meet him in the lobby of the Prudential Plaza (where the radio station was located). Since it was 1998, neither person knew what the other looked like--thus making it a truly blind date. Jack explained that he could easily spot his "dates" by scanning the lobby to find the nervous-looking women who stood alone. Once he spotted them, if he didn't find them attractive, he would make a lap through the lobby and then leave. Jack was a piece of work.