Kathie Lee Gifford Dropped These Hints About Her New Relationship That Many Viewers May Have Missed

Gifford moved down to Nashville, Tennessee, after she quit her job on NBC’s hit morning show Today. She left the fourth-hour segment back in the spring of 2019, and she made no secret of her willingness to bring some romance into her life. After all, it’d been some years since she’d lost long-time husband Frank.

The morning TV legend adored Nashville, finding it a laid-back treasure. As she told her former Today coworkers during a November 2019 appearance, “There’s a different culture down there,” she explained. “It’s a culture of kindness in Nashville. They are authentically kind. They are joyful, they have so much fun.”

Still, Gifford isn't ready to retire just yet. She recently made a film for Hallmark called A Godwink Christmas: Meant for Love. As she explained, “It took me a while to convince Hallmark that there’s a huge demographic of people out there that don’t want faith taken out of stories.” But the question remained, was she missing what she left behind?

No, Gifford wasn’t missing Today, despite her success on the program. In fact, she admitted to People in May of 2019, “I haven’t watched the show once." Then she continued, "I never watched the show when I left Regis [Philbin]. When I leave, I leave with a lot of love in my heart but dreams for the future. I never look back, you can't."

Staying focused on the future has come in handy throughout Gifford’s professional career. Her early days in the beauty pageant circuit brought her into contact with Anita Bryant, who suggested a foray into the world of Christian entertainment. But her time with Bryant didn’t bring Gifford the success she’d hoped for, and she soon quit, though she remained interested in spreading the gospel.

Bryant had gotten Gifford a spot at Oklahoma’s Oral Roberts University, and Gifford was soon part of Roberts’ singing squad. From 1972 she could be seen on the college’s TV show and at shows across the Bible Belt. But she soon saw through Roberts’ double standards and moved on to bigger and better things.

A chance visit to the set of Days of Our Lives led to a part on the soap, which lasted for close to year. Gifford’s voice also made her money as she sang for the show Name That Tune and on commercials. Her career was beginning to take off, with a sitcom role and appearances at Nevada casinos ensuing.

Then came the break that really made Gifford a household name. Regis Philbin tapped her as his sidekick on Live With Regis & Kathie Lee, which began in 1985. When it went national three years later, America just loved their banter, particularly the 15-minute live intro chat. And it adored Kathie Lee.

The program ran until 2000, when it was still among the nation’s top four talk shows. But Gifford had had enough, and she planned to focus on her family life and her music. It wasn’t until some years afterwards that she admitted that a big factor in her leaving Live was that her dad didn’t have long to live. He passed in 2002.

But the lure of TV chat remained strong in Gifford’s life, and in 2008 she was back on the small screen. This time her co-host was Hoda Kotb, and the two were living it large on Today. Once more, her obvious chemistry with her colleague won the public’s hearts, with the duo downing a glass of wine or two while mulling over the day’s events.

The TV legend had other side gigs, of course, and she could also be seen on Broadway. But it was her long years as a fixture of the chat world that saw her inducted into the Hollywood Walk of Fame in 2021. That wasn’t her only reward from life, of course, with a net worth that’s been reported to scale $60 million.

Away from the world of showbiz, Gifford had some romantic ups and downs. She married composer Paul Johnson in 1976, but that didn’t go well. “I was excited about starting a life with someone, but he didn’t feel the same way,” she wrote in her autobiography, It’s Never Too Late. “I felt humiliated sleeping in my guestroom.”

Reflecting on that experience, Gifford continued, “It was so damaging to me on so many levels, damaging for me emotionally as a woman to be rejected after saving myself all those years. And then it was so disappointing on a spiritual level, because I had to ask the Lord, ‘How did I get this so wrong anyway?’ I don’t even like to call him my husband because he wasn’t in the truest sense of the word.”

Not wanting to live as a divorced woman, Gifford kept trying for six long years. Then Johnson quit her. “I was relieved,” she admitted about that development. “I realized, you know what, we can make all the vows we want in life, but if both people don’t want the same thing, it’s not going to work out. And I was very hopeful that one day I would find a real love.”

Luckily, the chat icon did find love with Frank Gifford. He’d been a football star and met her when he was working on TV. This time, marriage worked. She wrote, “Our almost 30-year marriage was a real love affair and a true marriage in every sense of the word, so God redeemed.”

There was one small glitch, though, which came when a tabloid ran a report of Frank’s infidelity in 1997. Gifford was absolutely devastated to find out, especially as the revelation occurred at a low point in her business life. “Nobody knows what I went through,” she recalled. “You feel hopeless, and you don’t want to live anymore.”

Again, Gifford had to face the possibility of divorce. But she was sure the incident had been a one-off. “If this had been chronic behavior from Frank, I would have divorced him like that,” she claimed. “After what I’d been through with my first marriage, then to be with a chronically unfaithful husband, no. Nothing in the Bible says we have to stay with that.”

When Gifford went to see a counselor, they suggested forgiveness as the couple had kids together. And she decided that was the right course of action. “That guy I adored, and that’s why we were able to turn it around,” she explained. “It was the right thing for my life to forgive my husband. And then work at forgetting.”

“He was a very good, dear, gentle, generous man,” Gifford concluded about her husband. “So many things about him that I valued as my friend, I continued to value in him as my husband and the father of my children. But the person you loved the most in your life is the person that can hurt you the most.”

Sadly, the happy marriage came to an end with Frank’s sudden death in 2015. He’d suffered some of the symptoms of dementia, and his family suspected that a life of being bashed in the head as a footballer had done him harm. A fair bit older than Gifford, Frank was 84 when he passed.

The marriage had been blessed with two kids, with Cody arriving in 1990 and Cassidy following in 1993. Each of them married in the summer of 2020 with small, intimate ceremonies. “At both weddings, we just felt Frank just smiling,” Gifford wrote. “He had an aerial view, I think.”

But what about Gifford? Was there still room for romance in her life? Well, she told TV gossip show Entertainment Tonight in January 2020, “Of course I’m open [to dating]! Who says I’m not dating somebody?” If she was, though, she was keeping it quiet. And Gifford pointed out that she was “picky” with her men anyway.

Actually, Gifford told the Page Six website that she’d been quite active in the dating world, albeit without great success. “I think I dated four different gentlemen, and they’re all great guys, but they’re not the guy for me,” she revealed. “If I fall in love again, it will be because God just made it happen.”

Mind you, it wouldn’t necessarily be easy for the chat legend to meet men. During an appearance on Peacock’s Holiday Steals and Deals show, she said, “When people ask me, ‘Are you looking for love?’ my attitude has got to be, well, I’m not actively looking for it. I can’t go on websites, and you know, dating apps and all that kind of stuff.”

Still, for someone who claims to be “picky,” the TV queen wasn’t asking for too much. “I’m just looking for a guy that’s got real teeth. That’s it,” she told Extra in September 2020. And what did she have to offer? “Oh, I got some gams,” the modest star replied. “That’s about all I’ve got left.”

After all, Gifford couldn’t hope to replace her late husband. “I don’t expect any man to ever fill my husband’s cleats, nobody will ever be Frank Gifford,” she admitted. “I’m not looking for that. I’m not looking for anything. If he comes along, I’ll know. I’m not looking, I’m busy.”

But good things can come along even if you aren’t looking – and former co-host Hoda Kotb had news on that score. She could certainly claim to be an insider, even though there were whispers that her friendship with Gifford had suffered a little when Kotb had a baby. The once close pair had drifted apart, or so rumor had it.

Mind you, the pair themselves display an enduring friendship in public. Gifford posted on Instagram to celebrate her co-host’s birthday, labeling her “an Egyptian goddess.” And Kotb told Andy Cohen on his show Watch What Happens Live in July 2021 that they were constantly in touch, and that Gifford was thriving.

In fact, when Cohen asked her about Gifford, Kotb dropped a stunning revelation. The Egyptian-American said, “She’s happy. She’s in love. She’s in love, she’s in Nashville, she’s singing. She’s doing all the things she enjoys.” Perhaps a new era really had begun for Gifford, then. Kotb added, “When you think you’re at the end of a chapter, she’s living proof that you have no idea.”

Mind you, keen watchers of Today had already learned a little about Gifford’s new love interest in April of 2021. She’d revealed, “I’m in a really special relationship with somebody that is nice and fun and healthy, and so that’s good.” But she wasn’t giving much more detail than that about the romance.

Not that the Today team were just going to leave it at that, of course! No, they were keen to find out a lot more. So Savannah Guthrie wanted to know what exactly they were discussing. “Like a boyfriend, Kath?” she enquired. And Gifford straight away realized that she’d maybe let the cat out of the bag.

“It’s just happy, and I don’t want to mess it up,” Gifford said. “And I probably already have by just even mentioning it.” But the TV legend wasn’t mincing words about how she was doing. Gifford added, “To be in a place where you feel like every aspect of your life is good, that nothing’s missing, and that’s a beautiful place to be. I’m just so grateful.”

But though Gifford wouldn’t give out a name or any personal details, she was prepared to discuss some of the man’s qualities. “I’ve just found somebody that is so much fun to be with,” she revealed. “He is challenging to me. He’s the smartest person I’ve ever met, but he’s funny.”

“And we have a great time together, and so at this point in my life that’s exactly what I need and exactly what I want, you know?” the chat legend continued. “Different seasons of life – we weren’t meant to know each other before, it’s right now. We don’t know what the future holds at all, but we’re having fun today.”

When visiting Today in November 2019, Gifford had described an encounter that might shed light on the new man. “I went out with friends to a club to hear my favorite band down there,” she said. “I went to hear them, and this sweet guy asked me to dance. And so I said, ‘Okay.’ And then he just disappeared into the crowd. And then, you know, a couple weeks later, same band – Tim Akers & the Smoking Section – so we danced again.”

It didn’t end there, either. Gifford added, “And then we just went out a couple times. It was fun because I hadn’t been on a date in 33 years. It’s surreal. The world has changed so much. He was a gentleman. It was fine, it was fun.” But who was this fun man?

Well, in the summer of 2019 Gifford had had a fling with a guy with the name of Randy Cronk. She didn’t ever say who he was, but she was pictured smooching with him. And U.K. newspaper the Daily Mail ran a video of her dancing with a stranger who was readily identifiable as Cronk. Gifford was certainly having fun!

Ohio native Cronk’s a bit younger than Gifford, by a decade in fact, so he brings plenty of energy. He works in insurance, acting as president of an affiliate of Nationwide. Back in his younger days, he graduated in computer science from the University of Southern Mississippi, but nowadays he lives in Tennessee.

That Cronk was Gifford’s boyfriend seemed to be confirmed in July 2019 when she posted a picture on Instagram. In the photo, he’s standing close to Gifford with his arm wrapped around her. And reports had it that she’d been seen kissing the man, too, so certainly something was going on between them. But was he the guy Kotb said Gifford was in love with? We still don’t know…