Here is a good story about a fan who did not win the contest to meet Paul during the "Broadstreet" promoting, but did have several meetings with him that day. It comes from the Feb/March 1985 issue of the Write Thing and was written by Mike Matela.
It was a rainy and windy night in Chicago. I arrived at the Ambassador East about 10pm and saw a few people sitting out in front holding signs and pictures of Paul McCartney. I tried sneaking up, but I took one step off the elevator and was informed to please go back down, that's when I knew for sure hew as there. So the wait started. I lasted until one in the morning and went home dejected. I set my clock for five am because I heard he'd been jogging the other day. October 19, 1984, five o'clock came and jumped out of bed and headed back downtown Chicago. A 25 minute ride took fifteen minutes. I was flying! When I got there the same devoted girls were still there from last night. I have to give them a lot of credit. And the wait continued and it got colder and colder and much more windy. We all stood by the entrance hoping to get a glimpse of Paul. Then the next thing you know a voice comes out saying, "excuse me, I'm running late." It was Paul! He was coming in from jogging by himself. Everyone there was shocked. While we were looking for him to come out, he must have run right by us. Luckily I somehow managed to take a slightly out of focus shot. That sneak! After that meeting my adrenaline was so high, I knew there was no way I was leaving.
Three limos pulled up about 9am, and people began to sense something was going to happen. About 9:15 he came out with Linda beside him. Before you knew it, he was surrounded by people. Luckily I got to take a couple of shots. After he hopped into his limo another Beatle fan I'd met named Rich asked me if I wanted to hop into his car and follow him to the Ritz Carlton and of course I said yes. We actually blew two red lights on Michigan Avenue, trying to keep up wit Paul. We got there in time to catch him coming out of his limo. We then found out he wouldn't be out for about three hours. So I went to get some more film. Later I found out that ten of my best pictures didn't come out because I trusted the lady there to load my camera. Later on, back at the hotel we found out he was having lunch on the 12th floor and we shot up there and sat around. And before you know it, he popped up, walking right toward us. He came over and said hi, hugged the girl I was with (they died!) and then let me take those 10 pictures I was talking about. Then he said he had to run because he had an interview with Gene Siskel. Believe me, it was all too good to be true.
I got to meet him one more time about an hour later, which proved to be the highlight of the day. He came out wit h the press and I caught up to him and asked him for an autograph. He said "sure." I shook his hand and said, "thanks for everything Mr. McCartney." And that was it. I'm still to the moment on cloud nine!
Side note from Sara: The interview with Siskel was where Paul asked Siskel what he thought of the film and Gene admitted that he thought the whole thing was terrible. It was reported that Paul was VERY mad at this and was close to throwing a glass of Orange Juice at Gene Siskel!