So Kate Plus Date didn't work out quite as well as she'd hoped. 

Having finished up last summer's TLC journey with a vow to keep in touch with one of her suitors, Kate Gosselin later revealed that he was also keeping in touch with another lady. "Unfortunately, After keeping in touch with him for a few months, I found that Jeff had been dating someone since before our second date (?!?!)" she revealed in the comments section of a July Instagram post.  "I am in this to find my someone, but perhaps he didn't take it as seriously?" 

It was an unpleasant end, but not one that affected her stance that true love was out there. "I was definitely interested," the 45-year-old wrote, "but ...... onwards and upwards ....#MoreFishInTheSea"

Jon Gosselin, Colleen Conrad

Instagram

After all, her ex has already snagged one.

A decade since their largely contentious divorce was finalized, Jon has settled into a four-year romance so serious that it's got him thinking about diving into matrimony once more. As he marks his 43rd birthday today, the father of eight is likely to celebrate with two of his 15-year-old sextuplets—he was awarded temporary legal and physical custody of son Collin last December and daughter Hannah lives with him full-time—and registered nurse Colleen Conrad, the woman who's been a part of his orbit since his childhood. 

And though he'll be the one blowing out the candles, Conrad may just walk away with a big present. "I've thought about it, yeah—talked about it," he told reporters of engagement plans at WE tv's Real Love: Relationship Reality TV's Past, Present & Future panel in December 2018. "She's driven. I've known Colleen my whole life. We grew up three blocks from each other. Her sister used to babysit me."

So maybe that type of longevity bodes well for this potential union. Either way, it seems unlikely it could go any worse than his first. 

Back on the 2007 premiere of Jon & Kate Plus 8, the laid-back former I.T. specialist and the no-nonsense pediatric nurse seemed merely unhappy with Kate lamenting tending to Jon often felt like having a ninth child and Jon complaining about her being bossy. (Their sizable brood was made up of now-19-year-old twins Mady and Cara along with sextuplets Collin, Hannah, AlexisAadenLeah, and Joel.)

But as their ratings soared—a record 4.6 million tuned into the 2009 season four finale—their relationship plummeted. And though Jon has since claimed their young love was doomed from the start, opining on The Dr. Oz Show in November, "I think eventually, because of personality, it would have fizzled out anyway," the end was more of a catastrophic flame out. 

Jon Gosselin, Kate Gosselin, Jon and Kate Plus 8

Karen Alquist/TLC

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

Brad Barket/WireImage.com

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." (Well, everyone needs goals.)

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."

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?"

Kate Gosselin, Steve Neild

Splash News

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 then-22-year-old Hailey Glassman, the aforementioned daughter of a plastic surgeon. But none of them shocked quite as much as Stephanie Santoro

The then-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 dalliance. 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." 

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."

Jon Gosselin, Hailey Glassman

INFphoto.com

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." 

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." 

Kate Gosselin

Angela Weiss/Getty Images



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. 

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'!"

Kate Gosselin, DWTS

ABC

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, mom of two Conrad. 

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.") 

Jon Gosselin, Colleen Conrad

TheImageDirect.com

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." 



The same could be said of his bond with his other six kids. Though he's with Hannah and Collin full-time, "The other four [sextuplets] aren't talking to me," Jon recently revealed to E! News. (Twins Mady and Cara have also made their stance known, declaring in a 2016 interview with 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.")

Though it's unlikely Jon can be thrilled with the current arrangement, "It's what the kids want to do," he said. "If they don't want to talk to me, that's fine, as long as they keep up with their sibling connections." 

It was not quite four years ago he was complaining that he hadn't seen Collin in a year and a half, causing Kate to come clean to Good Morning America, revealing the tween was receiving treatment for educational and social challenges.

"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."

Jon Gosselin, Christmas 2018, Collin Gosselin, Hannah Gosselin, Colleen Conrad, Jesse Conrad, Jordan Conrad

Instagram / Jon Gosselin

But with Collin released from his school just before Christmas 2018, the holidays became especially celebratory for Jon. On Dec. 4, a Pennsylvania judge granted him temporary custody of the teen. 

"We won in court. That's, like, a big win," he told E! News at the time. "It'd be easier for one parent to just transition him home and he wanted do live with me so it was easier to do it that way." While he was thrilled, he said, he wasn't the only one: "Hannah is excited that her brother is coming home." 

To hear Jon, tell it, the thrill of victory was short lived. As recently as February, he was giving an interview on podcast First Class Fatherhood claiming there was a rift between the kids that live with him and the kids that live with Kate. "Right now, it's very tumultuous, pretty much, because there's no contact between Collin and his other siblings," he shared. "There's contact between Hannah and the other siblings." (Kate didn't respond to requests for comment.)

On the glass-half-full front, however, he and Kate had reached a somewhat unsteady détente, in that they'd agreed to leave most of the haggling to their team of attorneys. 

"So, if they decide to go live with mom or they decide to live with dad, it's up to them," Jon explained. "We do have a guardian ad litem, so it's like having a third parent, if there is a dispute between mom and dad, they can always call the guardian ad litem and she is a representative of the court and the judge, so she can make a better decision if there's a dispute between mom and dad."

Well, history would tell us the safe money is on that happening once or twice. 

(Originally published April 1, 2019, at 3 a.m. PT)

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