Kate Gosselin, Jon Gosselin

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When it comes to dating, three isn't a crowd for Kate Gosselin. Four is fine too. Maybe 10?

Because while the reality star is definitely ready to find a new man—nearly a decade after filing for divorce from ex-husband Jon—she can't stomach the idea of dating like an ordinary person. Not when her life these days is so, well, extraordinary.

"If I'm going to date someone, I can't just go out on a date—it's creepy to me to think of just going out somewhere with some stranger," she explained to People of her reasoning for signing up for her latest TLC series, Kate Plus Date, "and so I actually feel like doing it like this is the best and safest way for me to go on a date—a camera crew will be there! I'll be safe!" As an added bonus, she said, "The person will have been vetted by a matchmaker."

And while she could scroll through a dating app and do her own investigations, "I put my profile in there and people will know who it is within 90 seconds," she explained. "No, this is probably the safest way for me to date, let's be honest."

Of course no level of protection can prevent the romance from imploding like her last documented relationship. On the 2007 premiere of Jon & Kate Plus 8, the laid-back former I.T. specialist, 41, and the no-nonsense pediatric nurse, 43—parents to Mady and Cara, now 16, and sextuplets Alexis, Hannah, Aaden, Collin, Leah, and Joel, now 13—seemed merely unhappy with Kate lamenting tending to Jon often felt like having a ninth child and Jon complaining about her being bossy.

But as their ratings soared—a record 4.6 million tuned into the 2009 season four finale—their relationship plummeted.

First it was that Jon, then 31, was partying with college co-eds a few hours away from the pair's new $1.3 million five-bedroom Berks County, Pennsylvania mansion. Then, Us Weekly alleged he was having an affair with a grade-school teacher named Deanna Hummel. By the time Kate filed for divorce June 22, 2009 their split was so acrimonious, even their statements to the media—normally polished by publicists and filled with loving platitudes—were openly hostile. After Kate said Jon's "activities" left her with left her with "no choice but to file legal procedures in order to protect myself and our children," he responded, "I have always done everything I can to protect our family." 

Things unraveled from there. As tabloids splashed the duo across covers—they graced upwards of 50 in 2009—and none other than Vanity Fair dubbed them the biggest celebrity story of the year, both Jon and Kate seemed to be angling for the same prize: Who would win the media war and emerge from the divorce most beloved by fans? 

Kate Gosselin, Jon Gosselin

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At first it seemed Kate was a shoo-in. After all, Jon followed up his fling with Hummel (Us reported they met at local bar Chill Lounge when he sent over a shot) by jumping into a relationship with the college-aged daughter of Kate's tummy tuck doctor. And even before he split from Kate, he told the May 2009 issue of Ladies' Home Journal, "I always thought I'd be, like, 54-years-old and marry a 19-year-old or something."

But Kate's penchant for insults—during one episode Jon whined, "You yelled at me in there like I'm a frickin' dog,"—turned the unemployed tech specialist into the sympathetic character. "In news focus groups," Richard Spencer, then the editor of In Touch Weekly, told Vanity Fair in 2009, "it was amazing to me that readers were actually on Jon's side. 'Well, you know what, she's been awful to him. I don't blame him for having an affair.'"

And then there were the headlines alleging that Kate actually cheated first, with her ever-present, distinguished and very married bodyguard Steve Neild. Kate labeled the reports "disgusting, unthinkable, unfathomable," but Jon still managed to fan the flames. 

"I speculate, but I don't know," he admitted during an appearance that September on Good Morning America. "When they were traveling together, I felt jealous. Here I'm Mr. Mom. And then there's some other guy traveling with my wife."

Kate Gosselin, Steve Neild

Splash News

But as Jon uprooted his life in Pennsylvania for an apartment on New York City's Upper West Side, a pair of cubic-zirconia earrings and a wardrobe of Ed Hardy apparel, the tide began to shift. It wasn't just that Jon was partying in Vegas, hanging out with the likes of Kevin Federline and Michael Lohan and bragging to associates he could walk up to P. Diddy in a club with a casual, "What's up, Sean?"

There were also the women. So many women. After Hummel (who never confirmed their romance), there was Star reporter Kate Major, who would go on to marry Michael Lohan, and 22-year-old Hailey Glassman, the aforementioned daughter of a plastic surgeon. But none of them shocked quite as much as Stephanie Santoro

The 23-year-old former waitress, who spent one month as the kids' nanny, sold her story to In Touch. Under a headline blaring "Nanny Admits Affair with Jon!" she claimed they had a passionate affair. One time, when they were in the backyard hot tub, "I was scared one of the kids was going to pop their heads out," she alleged, "but he told me to relax." 

Jon Gosselin, Hailey Glassman

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That fall, TLC made a clean division from Jon, rebranding the show as Kate Plus 8

But Jon still found ways to log camera time. The reality vet, who's said he never wanted to be sign on to the show, appeared on Larry King Live Oct. 1, 2009 to announced he'd had "an epiphany." He no longer wanted his children to film. 

"It's not healthy for my kids to be on the show," he insisted. "It's detrimental to them."

After Jon filed a lawsuit seeking to shut down production of the show, his lawyer, Mark Heller, announced that a Pennsylvania Department of Labor and Industry investigation would show "they never got a permit for the kids to act." Jon also issued a public apology for his post-split womanizing and filed paperwork to stall divorce proceedings for 90 days in the hopes he and Kate could "restore our relationship." 

Kate Gosselin

Angela Weiss/Getty Images

By that point, their connection was almost irretrievably broken. On Oct. 5, Kate made a tearful appearance on the Today show explaining Jon had defied a court order and drained $230,000 from a joint account, leaving her just $1,000. (While Jon denied her allegations, he was later ordered to return $180,000 to Kate.) "You've left your children and their mother unable to pay for the roof over their heads," she exclaimed, adding that when she told the kids Jon had caused a halt in production, "There was wailing and sobbing. They love our crew, they love the interaction, they love the events. There is nothing harmful about it. They are angry." 



The pair's divorce was finalized that December. 

In 2010, Kate attempted a new routine. With long extensions replacing her much maligned, gravity defying 'do, she stumbled her way through a stint on Dancing With the Stars. In 2013, she appeared on an episode of Celebrity Wife Swap and two years later she followed that up with The Celebrity Apprentice. In between, the four-time author would shoot sporadic seasons of Kate Plus 8 where she would tour Australia and New Zealand with her brood, take them to space camp and even attempt blind dating. 

Kate Gosselin, DWTS

ABC

Off-camera, she revived old rumors when onlookers claimed to have spied her and Neild holding hands at a 2014 Demi Lovato concert. Other reports linked her to millionaire businessman Jeff Prescott, a romance Kate never confirmed. When their split was revealed in 2015, she tweeted, "There was no breakup recently/at all. Gotta b in a relationship in order 2 'break up'!"

Jon, meanwhile, continued his hunt for a new partner. He ended his tempestuous romance with Glassman in 2009 after they fought mid-interview on Entertainment Tonight and linked up with aspiring law student Morgan Christie during a 2010 snowboarding vacation in Park City, Utah. A romance with Liz Jannetta followed, but fizzled after he likened her to Kate during a 2014 appearance on VH1's Couples Therapy and then they both admitted to cheating on each other. Later that year, he met—and quickly moved in with—his current girlfriend, registered nurse and mom of two Colleen Conrad

Jon Gosselin, Colleen Conrad

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His list of everyman jobs was even longer. He installed solar panels for Green Pointe Energy, worked as an I.T. administrator, took a part-time cooking job at TGI Fridays, booked regular DJ gigs and even made a one-time appearance in the "Untamed Male Revue" at Atlantic City's Dusk Nightclub. (While he didn't strip, he did perform a few clothed lap dances explaining to E! News, "I wanted to give myself the best 40th birthday present ever.") 

When Entertainment Tonight caught up with him in 2013, he was living in an Internet-free cabin and waiting tables at nearby Black Dog Cafe. 

"At first I was nervous because I was like, 'How are people going to react?'" he said. "But then I'm thinking, 'Well it's fun and I get to talk to people.' And they technically already know me…they're like 'Are you the guy?' I'm like, 'Yeah, I'm the guy.'"

Though there's still one person he's unable to exchange pleasantries with. His relationship with Kate had been reduced to "text and email" he told Entertainment Tonight. "That's it." 



In their current arrangement—Jon has partial physical custody; Kate has full legal custody—he doesn't pay child support because "we both support financially." While he said Kate "takes care of school and all that stuff," he handles "the exact same things she takes care of. I buy their own groceries. They have their own groceries at my house, their own bedrooms, their own stuff. It's doubled." 

And should he go to Kate's to pick up the kids for visits, "the nanny comes out and I exchange the kids at her gate or at the bus stop. I don't physically see her."

Kate Plus 8, Kate Gosselin, 2014

TLC

Because while his life looks different now, those same arguments remain. Jon grumbles he doesn't get enough time with their brood, Kate responds that if that's the case it's because they don't want to see him.

"I give the kids…some of the kids visit and some don't and I keep the peace," she said at a Television Critics Association panel in January 2015. "That's what I've always done. It's best for the kids." 

And when Jon complained in 2016 that he hadn't seen son Collin in a year and a half, Kate came clean to Good Morning America, revealing the tween was receiving treatment for educational and social challenges.

Kate Gosselin, Twitter

Twitter

"It was not even really a choice. It was on the advice of his doctors and it had to happen," Kate said. "He's plodding along. We are, too. It was necessary. And I'll go to the ends of the earth for the best for each one of them. This is the best thing to do for him right now, and so that comforts me." As for Jon's claims that Kate won't tell him where Collin is being treated, "I'm really focused less on what Jon has to say...I don't really pay attention to be honest."

Though at times their friction is impossible to ignore. Just last August Jon called police to Wyomissing, Pennsylvania's ROG Orthodontics after he and Kate launched into a verbal altercation over which parent one of their 13-year-old daughters would go home with. 

And Jon, who filed for custody of Hannah in 2015 because, says a source, "She is unhappy and uncomfortable in the house with Kate," insists he's not done battling for his kids.

Telling E! News that Jon is making an effort to "do what is right," his attorney Kristen Doleva-Lecher said last year, "It should be known Jon has been aggressively and relentlessly fighting for his kids."

Kate Gosselin, Cara Gosselin, Mady Gosselin

Doug Meszler/Splash News

But with a few of them, he may be in for an uphill battle. Back in 2016, 17-year-old twins Mady and Cara revealed they're not on speaking terms with Jon. "He makes it seem like we're being kept from him, which is insane," Mady told People. "He should maybe spend some time thinking about why we don't want to see him, and maybe realize that if he ever does want a relationship with us, talking about us on TV is not the way to make that happen."

Besides, they're far too busy for their dad's drama, she added: "This year I'm going to turn 16. I'm going to be learning to drive, taking the PSATs, thinking about college. So much is going on in my life. And the last thing I have time for is a toxic relationship."

Kate Gosselin

Marcus/Zodiac/Splash News

Though they are eager for their mom to take on a new one, which leads us back to Kate's future dating show, which will air this fall. "Now that they're older and talking about dating and how they're all gonna get married someday…it became apparent: they want someone for me," she told People. "They want me to have somebody in my life."

Her ideal man, says Kate, who's copped to having a crush on Patrick Dempsey, would be confident with a set career: "A grown-up with their own life, their own agenda, who knows who they are." He also must love dogs and be a good listener. "I would love my kids to have a mutual friendship and respect with this guy," she told the mag, "and for him to be someone they can ask for advice."

Expect Kate to be particular during the search. Noting some women make the mistake of settling and "being with the first person that comes along," she has said, "This time around, I have to be extra choosy." Though she allows, "If you're willing to take on someone with eight kids, you have to be pretty darn tough." 

Tough enough, ideally, not to bend under the pressures of fame.

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