1991 Winner: Bob Anderson

Just like Romeo and Juliet, the love story of Bob and Freda Anderson features a romantic balcony scene. Stunning enough for a Hollywood movie, the setting is Waikiki. Bob Anderson gazed at Hawaii’s splendors from his fourth floor balcony when his eyes fell on an even more engaging spectacle―a beautiful woman sunbathing at the hotel’s swimming pool. He scurried downstairs to meet the lady, Freda Segall.

“He struck up a conversation and invited me out,” Freda said. “One of the few arguments we ever had was whether he proposed to me at the salad bar or over dessert. I still say it was over dessert.”

Most men would apologize for proposing suddenly on the first date. Anderson did apologize, but it was for not asking her sooner. Perhaps before the hors d’oeuvres.

Although Freda flew back to England and Bob returned to his home in Santa Fe, New Mexico, those seeds of love tossed from the balcony took root below. A month later, as Anderson retired from the Hollywood movie business, his friends in Los Angeles threw him a farewell party. He quickly invited Freda to join him.

“The best way to know a guy is to meet his friends,” Freda observed. She must have liked Bob’s friends a lot. Six months from the day they met, the two were married in Santa Fe.

If ever a union was predestined to fail, it was this one―a poster child for post marital problems. Bob was 62 years old. Freda was 32. He was Catholic. She was Jewish. He was American. She was raised in South Africa before moving to England. He was a prop master for major motion picture and television shows. She was a concert pianist. It was his sixth marriage. It was her first. Even Las Vegas would not have allowed betting on the miniscule chance of this marriage making it much further than the honeymoon.

“But I was the last and the longest,” Freda says warmly. “We were blessed with 16 years.”

Anderson left his mark on Hollywood in the vital role of making the props and sets perfect in such classic films as “To Kill a Mockingbird” and Cary Grant/Doris Day movies. Anderson often joked that he knew it was time to retire after he worked on the television pilot for Baywatch.

His first experiences with Key West came in the 1940s during U.S. Coast guard service. “He remembered having his first drink at Sloppy Joe’s back then,” Freda noted. “He also went to Cuba during the war, and he would have loved it if he could have retired there.”

First entering the contest in 1988, Bob remained a wannabe for three years, philosophizing―”The bottom line is not about the winning, it’s about the friendships that develop.”

After Bob lost for the third time, Freda informed her husband, “I don’t know if I’m ever going to come back, but you keep coming.”

But before leaving Key West, she discovered Colony Exclusive Cottages.

“I walked in and saw this phenomenal, all-tile pool and told him I’d come back one more time.”

She did. And he won.

“Bob had the most fun of any Papa,” Freda asserts. As a judge, he looked for contestants who would be committed to the festival and not just along to win, to have their moment of glory, and leave,” she said. “They wanted people who would continue the tradition.”

Born All Saints Day in Los Angeles on November 1, 1926, Bob appreciated and respected the trust granted him in the years he took part in the contest when Freda didn’t accompany him to Key West.

“I think this is a guy’s event,” she said, “and the good thing with our relationship is that he could go on his own and have a great time. I never worried about Bob, even though I knew girls with great boobs would surround him and buy him drinks. But he’d miss me and call me every night.”

Anderson lost his battle with cancer on November 22, 2004. Freda was by his side, and some of his fellow Papas made the long trek to their home in Scottsdale, Arizona, to comfort him during those last days and hours.

“People tell me, ‘You’re so positive,’” says Freda. “but I told Ron Thomas that Bob’s passing actually has given me a new life. I look at how much I have to be grateful for, partly on my own, but also because of my marriage to Bob. None of us know when our time is up, so every day is a blessing.”

As far as Freda Anderson is concerned, only Bob’s body has left the building. “His spirit is with me all the time. I think of him continually―the funny things, what we used to call Bob-isms.”

Freda represented her husband at the 2005 Hemingway Look-alike Contest. “ Before he passed away, Bob never asked me to go down and have one more good time with the guys. But I just felt it would be good closure for those who liked him so much. Some of them were pretty shaken up.”

Freda vows to return to the event that meant so much to her husband, and she plans to bring him along, too

“He’ll be in Key West with me, looking over those entry forms. He had a very full life and man’s love of life. But the main thing is that he wants those guys to have a good time. And at the end,” said Freda, “you look back at your life and decide what really mattered. And it’s always friendship and family.”