Jon Gosselin Relationship Historical past: Kate Gosselin, Stephanie Lebo, Extra

In terms of love, former actuality star Jon Gosselin has actually skilled his share of ups and downs.

Jon was married to ex-wife Kate Gosselin, with whom he shares eight kids, from 1999 till the pair's divorce in 2009. Although the Gosselins' marriage got here to an finish amid accusations Jon had ben untrue, he repeatedly denied the claims.

Since then, Jon has dated a number of ladies earlier than turning into engaged to Stephanie Lebo in 2024. On the time, Jon advised The U.S. Solar, “We're actually glad and in love. We're very snug with one another; it simply suits. Plus all our buddies are the identical folks, as an alternative of ‘your pals' and ‘my buddies.'”

However that happiness hasn't stopped him from commenting on his ex-wife's love life. In 2025, Jon shared a photograph of Kate and her rumored beau, Steve Neild, by way of Instagram and captioned it, “Guess who actually ruined the wedding. Learn for your self.”

He added: “Perhaps after I communicate folks will hear now!!!”

The pair's son Collin additionally accused his mom of being untruthful. “That is my formal invitation to do a lie detector check with my mother lol,” he wrote by way of his Instagram Story in 2025. “Then, we'll see who's been mendacity straight to the general public. I'm so severe by the way in which.”

Although Kate has but to answer to the accusations from her ex-husband and estranged son, Jon has had his personal justifiable share of fascinating relationship rumors over time. Maintain scrolling to learn Jon's relationship historical past.

Kate Gosselin

Jon and Kate married in June 1999. The pair appeared in Discovery Well being specials alongside their kids and sprang to nationwide stardom when their actuality collection Jon & Kate Plus 8 debuted on TLC in April 2007.

The collection centered on the pair's lives with their children: twins Cara and Mady and sextuplets Alexis, Hannah, Aaden, Collin, Leah and Joel.

Although Jon and Kate renewed their marriage ceremony vows in August 2008, they introduced their separation in June 2009 — months after rumors that Jon had been having an affair surfaced. In a September 2009 appearance on ABC's Primetime: Household Secrets and techniques, Jon claimed Kate was abusive. As he put it, “I used to be abused. I went by remedy.”

Jon additionally determined to cease filming the household's present, which was renamed Kate Plus 8 in October 2009 after he was sued by TLC for breach of contract. Jon filed a $5 million countersuit in opposition to the community in November 2009, however TLC prevailed and received the case in December of the identical 12 months.

In July 2009, Kate advised Folks of the cut up, “On a great day I really feel reduction. On a foul day I really feel failure. I've by no means give up something in my life. It seems like I've failed. It's laborious. That is the primary conflict I've fought alone. Actually, actually alone.”

She continued: “It was occasion after occasion after occasion the place I got here to appreciate: This isn't the identical individual I married. I bear in mind simply him and considering, ‘I wouldn't select to marry that actual individual proper now … so why am I right here?' Our objectives don't match up anymore, our desires don't match up, our concepts don't match up.”

Jon and Kate finalized their divorce in December 2009. Kate's determination to affix Dancing With the Stars the next 12 months appeared to immediate Jon to file for authorized custody of the pair's eight kids, and his lawyer described Kate as “an absentee mother” whereas she rehearsed for the present within the basement of the house she lived in with their children. On the time, Kate's then-attorney Mark Momijan advised RadarOline, “We haven't acquired any formal submitting but, however I can't think about something farther from the reality. Kate is a loyal mom. Her concern for the welfare of her children is so distinguished that any allegations like this report are reckless and so removed from the mark, it's offensive.”

Kate filed her personal swimsuit in opposition to Jon in August 2013 and accused of him of utilizing “unlawful hacking” to offer creator Robert Hoffman info for his ebook Kate Gosselin: How She Fooled the World. She dropped the case in November 2013.

In January 2016, Jon advised Steve Harvey had not “seen all [his] children collectively in about three years.” Twins Mady and Cara spoke to People in response in August 2016, with Mady explaining on the time, “He makes it seem to be we're being stored from him, which is insane. He ought to perhaps spend a while interested by why we don't wish to see him, and perhaps notice that if he ever does desire a relationship with us, speaking about us on TV will not be the way in which to make that occur.”

In April 2018, Jon revealed he had custody of the pair's daughter Hannah and introduced he was additionally pursuing custody of Collin, who was dwelling in a therapy heart for minors on the time. Collin moved in with Hannah and Jon in December 2018.

After Kate introduced she was in a brand new relationship, reportedly with the household's former bodyguard, Neild, in September 2025, Collin accused his mom of getting an affair with Neild in 2009. He and Hannah weren't pictured in images Kate shared by way of social media whereas celebrating the sextuplets' twenty first birthday in Might 2025.

Deanna Hummel

In Might 2009, 5 folks, together with two relations of Deanna Hummel's, advised Us that she and Jon had an affair. The third grade instructor's brother Jason advised Us, “She's a pleasant woman, not a homewrecker. He's a foul liar. This isn't wholesome for her. However she is refusing to assist herself, so right here I'm making an attempt to assist her myself. I hope this clears the air.”

Stephanie Santoro

In September 2009, the Gosselin household's former nanny Stephanie Santoro claimed she and Jon had an affair. Santoro told In Touch Weekly she labored for the household for one month, and through that point Jon invited her over and gave her a therapeutic massage. She additionally stated Jon advised her, “Effectively, I assume we will kiss simply as soon as” and “No matter you do, don't fall in love with me, as a result of it's going to be unattainable for me to not fall in love with you.” Jon denied the allegations.

Kate Main Lohan

Additionally in September 2009, former Star reporter Kate Main (now Lohan) stated she and Jon had a short-lived romance following his cut up from Kate — one other relationship Jon has denied. “I'll take a lie detector check, and I'd love for Jon to take a lie detector check as a result of for him to say there was no romance is a whole lie,” she advised HLN's Showbiz Tonight, per People.

She added: “If I may speak to Kate Gosselin, I'd positively. I feel we might have loads in frequent, and I really feel badly for her. I feel she's positively taking the excessive highway on this, and I'm positive it's very laborious and the very last thing I'd need is for any of his kids to see this, however then once more, I'm not the mother or father.”

Hailey Glassman

Hailey Glassman, a household buddy who's 10 years Jon's junior, and the previous actuality star dated someday after his cut up with Kate till their breakup in December 2009. In March 2011, Glassman told RadarOnline that Jon as soon as tried to blackmail Kate.

She stated: “We have been in mattress, and Jon known as Kate on speaker telephone. He wrote down what he wished to say to her after which he learn from his notes. He advised her, ‘You both give me cash or I'm going to name [Child Protective Services].'”

Glassman added, “Kate began screaming, and Jon simply began laughing. He simply laughed at her. Later, when he bought off the telephone, I requested him, ‘What are you doing? Why are you doing this? That is the mom of your eight kids!' And he advised me, ‘Oh, you don't know what I went by along with her, what I needed to cope with.'”

In response, Jon wrote on X (then Twitter), “Radar On-line has been duped once more by Hailey Glassman, who is seemingly and not using a job and determined for cash. This text comprises so many lies, they're too quite a few to rely. It's utterly false and with none advantage.”

Morgan Christie

Rumors that Jon was relationship then-law scholar Morgan Christie surfaced in January 2010. The pair attended the Sundance Movie Competition collectively the identical month, however Morgan ended issues in March 2010.

Liz Jannetta

Jon and Liz Jannetta, a mom of three, met in February 2012. That Might, she advised Inside Version, “I didn't watch the present. Something I knew about Jon was from the tabloids. You already know, womanizer Jon.” The pair have been collectively for 2 years, throughout which they appeared on the fourth season of VH1's collection {Couples} Remedy. They broke up in 2014 after Jon stated on the collection, “When Liz laughs at me and walks away, it's like Kate. That's precisely how I really feel.”

Colleen Conrad

Jon introduced his relationship with nurse practitioner Colleen Conrad in mid-2014. The pair dated for seven years till their cut up in August 2021, 4 months after Conrad was identified with breast most cancers. “We had ongoing points earlier to our breakup and former to her analysis, so we had hassle within the relationship for a very long time and didn't actually need any stress throughout her therapy,” Jon stated on The Dr. Oz Present. “So we thought it was greatest that we simply cease our relationship and work on our friendship and get her by her therapy.”

Stephanie Lebo

Jon and Lebo went public with their relationship in August 2023 once they advised The U.S. Solar that they had begun relationship after his cut up from Conrad. “He had ordered me a creme brûlée cheesecake, so it was ready for me after I arrived, which is tremendous candy, however I don't like cheese, in order that was type of humorous,” Lebo advised the outlet of their first date.

Lebo added that the pair bonded over their previous relationships. “Now we have a lot in frequent as a result of we've each been with people who find themselves not one of the best for us, however we wouldn't recognize what we've collectively if it wasn't for these experiences,” she defined.

Jon and Lebo introduced their engagement in December 2024. He later advised Leisure Tonight that he “would positively” invite his estranged children to their marriage ceremony.