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

In relation to 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 youngsters, 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 getting engaged to Stephanie Lebo in 2024. On the time, Jon informed The U.S. Solar, “We’re actually glad and in love. We’re very snug with one another; it simply matches. Plus all our associates are the identical individuals, as an alternative of ‘your folks’ and ‘my associates.’” They wed in 2025.

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, through Instagram and captioned it, “Guess who actually ruined the wedding. Learn for your self.”

He added: “Perhaps after I converse individuals 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 take a look at with my mother lol,” he wrote through his Instagram Story in 2025. “Then, we’ll see who’s been mendacity straight to the general public. I’m so critical 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 fair proportion of fascinating relationship rumors over time. Hold 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 youngsters and sprang to nationwide stardom when their actuality sequence Jon & Kate Plus 8 debuted on TLC in April 2007.

The sequence targeted on the pair’s lives with their youngsters: 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 look on ABC’s Primetime: Household Secrets and techniques, Jon claimed Kate was abusive. As he put it, “I used to be abused. I went via 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 towards the community in November 2009, however TLC prevailed and gained the case in December of the identical 12 months.

In July 2009, Kate informed Folks of the break up, “On a great day I really feel reduction. On a nasty day I really feel failure. I’ve by no means give up something in my life. It appears like I’ve failed. It’s exhausting. That is the primary warfare 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 particular person I married. I keep in mind simply him and pondering, ‘I wouldn’t select to marry that precise particular person 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 resolution to affix Dancing With the Stars the next 12 months appeared to immediate Jon to file for authorized custody of the pair’s eight youngsters, 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 youngsters. On the time, Kate’s then-attorney Mark Momijan informed 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 youngsters 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 towards Jon in August 2013 and accused of him of utilizing “unlawful hacking” to offer writer Robert Hoffman info for his e-book Kate Gosselin: How She Fooled the World. She dropped the case in November 2013.

In January 2016, Jon informed Steve Harvey had not “seen all [his] youngsters collectively in about three years.” Twins Mady and Cara spoke to Folks in response in August 2016, with Mady explaining on the time, “He makes it appear to be we’re being saved from him, which is insane. He ought to perhaps spend a while excited about 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 isn’t 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 through social media whereas celebrating the sextuplets’ twenty first birthday in Might 2025.

Deanna Hummel

In Might 2009, 5 individuals, together with two kinfolk of Deanna Hummel’s, informed Us that she and Jon had an affair. The third grade instructor’s brother Jason informed Us, “She’s a pleasant woman, not a homewrecker. He’s a nasty 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 informed In Contact 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 informed her, “Nicely, I suppose 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 not possible 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 break up from Kate — one other relationship Jon has denied. “I’ll take a lie detector take a look at, and I might love for Jon to take a lie detector take a look at as a result of for him to say there was no romance is an entire lie,” she informed HLN’s Showbiz Tonight, per Folks.

She added: “If I might discuss to Kate Gosselin, I might undoubtedly. I believe we’d have lots in widespread, and I really feel badly for her. I believe she’s undoubtedly taking the excessive street on this, and I’m positive it’s very exhausting and the very last thing I might need is for any of his youngsters to see this, however then once more, I’m not the guardian.”

Hailey Glassman

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

She stated: “We had been in mattress, and Jon known as Kate on speaker cellphone. He wrote down what he needed to say to her after which he learn from his notes. He informed 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 received off the cellphone, I requested him, ‘What are you doing? Why are you doing this? That is the mom of your eight youngsters!’ And he informed me, ‘Oh, you don’t know what I went via along with her, what I needed to take care of.’”

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 incorporates so many lies, they’re too quite a few to depend. It’s fully false and with none advantage.”

Morgan Christie

Rumors that Jon was relationship then-law pupil Morgan Christie surfaced in January 2010. The pair attended the Sundance Movie Pageant 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 informed Inside Version, “I didn’t watch the present. Something I knew about Jon was from the tabloids. You realize, womanizer Jon.” The pair had been collectively for 2 years, throughout which they appeared on the fourth season of VH1’s sequence {Couples} Remedy. They broke up in 2014 after Jon stated on the sequence, “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 break 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 via her therapy.”

Stephanie Lebo

Jon and Lebo went public with their relationship in August 2023 once they informed The U.S. Solar they’d begun relationship after his break 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 informed the outlet of their first date.

Lebo added that the pair bonded over their previous relationships. “We’ve got a lot in widespread as a result of we have now each been with people who find themselves not the most effective for us, however we wouldn’t respect what we have now collectively if it wasn’t for these experiences,” she defined.

Jon and Lebo introduced their engagement in December 2024. He later informed Leisure Tonight that he “would undoubtedly” invite his estranged youngsters to their marriage ceremony. They received married in November 2025.