After divorcing his first wife in 1981 following seven years together, Alex Trebek met Jean Currivan, a real estate project manager from Huntington, New York. The two crossed paths at a party in 1988; he later invited her to his home for dinner.

The prospect of dating Jeopardy!’s host, said Jean, made her “really nervous,” she told PEOPLE following their wedding in 1990. “I was afraid I’d mispronounce my own name! But Alex is really down to earth. He’s much more casual than he is on the show.”

On Jean’s 26th birthday in September 1989, Alex gave her black velvet pants and a matching bolero jacket. “I thought that was it,” she said. “Then he said, ‘Here’s a little something else,’ and he took out this little wicker box.” Inside was a 16-carat sapphire ring, surrounded by six carats’ worth of diamonds. “It took my breath away,” Jean told PEOPLE. “I mean, it was a rock.” Then he popped the question. “I went all dumb. I think I said, ‘What?’ ”

During the couple’s April 30, 1990, wedding, held before 150 guests at L.A.’s Regency Club, Trebek, always a jokester, responded to his critical cue by saying, “The answer is… yes.” 

In a 1990 interview with PEOPLE, the newlyweds insisted that their 24-year age disparity wasn’t a problem. “At first it worried me,” Trebek shared. “But then I thought, ‘The hell with it. We’ll make it work.’ ”

“I can understand why he was cautious about being with a younger woman,” said Jean. “So I didn’t try to push him. We just took it one day at a time.”

“Alex was looking for a Jean,” longtime friend Bob Murphy, once president of Merv Griffin Enterprises, told PEOPLE in 1990, “and he found her.”

Three weeks after the couple’s wedding, they discovered they were pregnant. Together they have two children, Emily, a real estate developer in L.A., and Matthew, a restaurant owner in N.Y.C.

In 2019, Trebek told PEOPLE he had just one regret in life. 

“My wife Jean and I have been together almost 29 years, and I was thinking about President Bush when he died, and all the comments about his life about what a nice guy he is, and how he and his wife had been together 73 years.  I thought, oh my gosh … if I’d just met Jean in my 20s we could have had a longer life together,” he said.

However, he added jokingly, “I guess if I’d met her when I was in my 20s she wouldn’t have been born yet. But hey, 29 years is pretty good!”

In his 2019 PEOPLE interview, Trebek told PEOPLE he and his wife are “homebodies.” “I told the staff the other day, I cooked dinner for Jean, and we went out to a movie. That was big day in the Trebek household,” he joked.

The couple’s togetherness will be all the more important as Trebek faces treatment for his stage 4 pancreatic cancer, a diagnosis he revealed publicly on March 6. 

“Now normally the prognosis for this is not very encouraging,” he said, “but I’m going to fight this.”

In a May 2019 interview with PEOPLE, the TV star shared that his doctors say he’s in “near remission.”

“It’s kind of mind-boggling,” Trebek added. Although the cancer has a 9 percent survival rate, Trebek has been responding very well to chemotherapy. “The doctors said they hadn’t seen this kind of positive result in their memory … some of the tumors have already shrunk by more than 50 percent,” he added.

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