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

Relating 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 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 constantly 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 completely satisfied and in love. We’re very comfy with one another; it simply matches. Plus all our pals are the identical folks, as a substitute of ‘your mates’ and ‘my pals.’” 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 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 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. Preserve 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 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 received the case in December of the identical yr.

In July 2009, Kate informed Folks of the break up, “On an excellent 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 looks like I’ve failed. It’s exhausting. That is the primary battle I’ve fought alone. Actually, actually alone.”

She continued: “It was occasion after occasion after occasion the place I got here to understand: This isn’t the identical individual I married. I bear in mind simply taking a look at him and pondering, ‘I wouldn’t select to marry that actual individual proper now … so why am I right here?’ Our targets don’t match up anymore, our goals don’t match up, our concepts don’t match up.”

Jon and Kate finalized their divorce in December 2009. Kate’s choice to hitch Dancing With the Stars the next yr 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 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 go well with towards Jon in August 2013 and accused of him of utilizing “unlawful hacking” to present writer Robert Hoffman data for his guide 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 look like we’re being stored from him, which is insane. He ought to possibly spend a while excited about why we don’t need to see him, and possibly notice that if he ever does need 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 remedy 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 Could 2025.

Deanna Hummel

In Could 2009, 5 folks, together with two family of Deanna Hummel’s, informed Us that she and Jon had an affair. The third grade trainer’s brother Jason informed 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 attempting 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 mentioned Jon informed her, “Properly, I assume we are able to 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 inconceivable 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) mentioned 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’d 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 a whole lie,” she informed HLN’s Showbiz Tonight, per Folks.

She added: “If I might discuss to Kate Gosselin, I’d undoubtedly. I believe we’d have so much in widespread, and I really feel badly for her. I believe she’s undoubtedly taking the excessive highway on this, and I’m certain it’s very exhausting 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 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 mentioned: “We had 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 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 telephone, I requested him, ‘What are you doing? Why are you doing this? That is the mom of your eight kids!’ And he informed me, ‘Oh, you don’t know what I went via together 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 with out a job and determined for cash. This text accommodates so many lies, they’re too quite a few to depend. It’s fully false and with none benefit.”

Morgan Christie

Rumors that Jon was relationship then-law pupil 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 Could, she informed Inside Version, “I didn’t watch the present. Something I knew about Jon was from the tabloids. You recognize, womanizer Jon.” The pair had 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 mentioned 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 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 bother within the relationship for a very long time and didn’t actually need any stress throughout her remedy,” Jon mentioned 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 remedy.”

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 sort of humorous,” Lebo informed the outlet of their first date.

Lebo added that the pair bonded over their previous relationships. “Now we have a lot in widespread as a result of we’ve got each been with people who find themselves not the perfect for us, however we wouldn’t admire what we’ve got 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.