When it comes to love, former reality star Jon Gosselin has certainly experienced his share of ups and downs.
Jon was married to ex-wife Kate Gosselin, with whom he shares eight children, from 1999 until the pair’s divorce in 2009. Though the Gosselins’ marriage came to an end amid accusations Jon had ben unfaithful, he continuously denied the claims.
Since then, Jon has dated several women before becoming engaged to Stephanie Lebo in 2024. At the time, Jon told The U.S. Sun, “We are really happy and in love. We are very comfortable with each other; it just fits. Plus all our friends are the same people, instead of ‘your friends’ and ‘my friends.’”
But that happiness hasn’t stopped him from commenting on his ex-wife’s love life. In 2025, Jon shared a photo of Kate and her rumored beau, Steve Neild, via Instagram and captioned it, “Guess who really ruined the marriage. Read for yourself.”
He added: “Maybe when I speak people will listen now!!!”
The pair’s son Collin also accused his mother of being untruthful. “This is my formal invitation to do a lie detector test with my mom lol,” he wrote via his Instagram Story in 2025. “Then, we’ll see who’s been lying straight to the public. I’m so serious by the way.”
Though Kate has yet to reply to the accusations from her ex-husband and estranged son, Jon has had his own fair share of interesting relationship rumors over the years. Keep scrolling to read Jon’s relationship history.
Kate Gosselin
Jon and Kate married in June 1999. The pair appeared in Discovery Health specials alongside their children and sprang to national stardom when their reality series Jon & Kate Plus 8 debuted on TLC in April 2007.
The series focused on the pair’s lives with their kids: twins Cara and Mady and sextuplets Alexis, Hannah, Aaden, Collin, Leah and Joel.
Though Jon and Kate renewed their wedding vows in August 2008, they announced 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: Family Secrets, Jon claimed Kate was abusive. As he put it, “I was abused. I went through therapy.”
Jon also decided to stop filming the family’s show, 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 against the network in November 2009, but TLC prevailed and won the case in December of the same year.
In July 2009, Kate told People of the split, “On a good day I feel relief. On a bad day I feel failure. I’ve never quit anything in my life. It feels like I’ve failed. It’s hard. This is the first war I’ve fought alone. Really, really alone.”
She continued: “It was event after event after event where I came to realize: This is not the same person I married. I remember just looking at him and thinking, ‘I wouldn’t choose to marry that exact person right now … so why am I here?’ Our goals don’t match up anymore, our dreams don’t match up, our ideas don’t match up.”
Jon and Kate finalized their divorce in December 2009. Kate’s decision to join Dancing With the Stars the following year appeared to prompt Jon to file for legal custody of the pair’s eight children, and his lawyer described Kate as “an absentee mom” while she rehearsed for the show in the basement of the home she lived in with their kids. At the time, Kate’s then-attorney Mark Momijan told RadarOline, “We haven’t received any formal filing yet, but I can’t imagine anything farther from the truth. Kate is a devoted mother. Her concern for the welfare of her kids is so prominent that any allegations like this report are reckless and so far from the mark, it’s offensive.”
Kate filed her own suit against Jon in August 2013 and accused of him of using “illegal hacking” to give author Robert Hoffman information for his book Kate Gosselin: How She Fooled the World. She dropped the case in November 2013.
In January 2016, Jon told Steve Harvey had not “seen all [his] kids together in about three years.” Twins Mady and Cara spoke to People in response in August 2016, with Mady explaining at the time, “He makes it seem like we’re being kept from him, which is insane. 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.”
In April 2018, Jon revealed he had custody of the pair’s daughter Hannah and announced he was also pursuing custody of Collin, who was living in a treatment center for minors at the time. Collin moved in with Hannah and Jon in December 2018.
After Kate announced she was in a new relationship, reportedly with the family’s former bodyguard, Neild, in September 2025, Collin accused his mother of having an affair with Neild in 2009. He and Hannah were not pictured in photos Kate shared via social media while celebrating the sextuplets’ 21st birthday in May 2025.
Deanna Hummel
In May 2009, five people, including two relatives of Deanna Hummel’s, told Us that she and Jon had an affair. The third grade teacher’s brother Jason told Us, “She’s a nice girl, not a homewrecker. He is a bad liar. This isn’t healthy for her. But she is refusing to help herself, so here I am trying to help her myself. I hope this clears the air.”
Stephanie Santoro
In September 2009, the Gosselin family’s former nanny Stephanie Santoro claimed she and Jon had an affair. Santoro told In Touch Weekly she worked for the family for one month, and during that time Jon invited her over and gave her a massage. She also said Jon told her, “Well, I guess we can kiss just once” and “Whatever you do, don’t fall in love with me, because it’s going to be impossible for me not to fall in love with you.” Jon denied the allegations.
Kate Major Lohan
Also in September 2009, former Star reporter Kate Major (now Lohan) said she and Jon had a short-lived romance following his split from Kate — another relationship Jon has denied. “I will take a lie detector test, and I would love for Jon to take a lie detector test because for him to say there was no romance is a complete lie,” she told HLN’s Showbiz Tonight, per People.
She added: “If I could talk to Kate Gosselin, I would definitely. I think we would have a lot in common, and I feel badly for her. I think she’s definitely taking the high road in this, and I’m sure it’s very hard and the last thing I would want is for any of his children to see this, but then again, I’m not the parent.”
Hailey Glassman
Hailey Glassman, a family friend who is 10 years Jon’s junior, and the former reality star dated sometime after his split with Kate until their breakup in December 2009. In March 2011, Glassman told RadarOnline that Jon once attempted to blackmail Kate.
She said: “We were in bed, and Jon called Kate on speaker phone. He wrote down what he wanted to say to her and then he read from his notes. He told her, ‘You either give me money or I’m going to call [Child Protective Services].’”
Glassman added, “Kate started screaming, and Jon just started laughing. He just laughed at her. Later, when he got off the phone, I asked him, ‘What are you doing? Why are you doing this? This is the mother of your eight children!’ And he told me, ‘Oh, you don’t know what I went through with her, what I had to deal with.’”
In response, Jon wrote on X (then Twitter), “Radar Online has been duped again by Hailey Glassman, who is apparently without a job and desperate for money. This article contains so many lies, they are too numerous to count. It is completely false and without any merit.”
Morgan Christie
Rumors that Jon was dating then-law student Morgan Christie surfaced in January 2010. The pair attended the Sundance Film Festival together the same month, but Morgan ended things in March 2010.
Liz Jannetta
Jon and Liz Jannetta, a mother of three, met in February 2012. That May, she told Inside Edition, “I didn’t watch the show. Anything I knew about Jon was from the tabloids. You know, womanizer Jon.” The pair were together for two years, during which they appeared on the fourth season of VH1’s series Couples Therapy. They broke up in 2014 after Jon said on the series, “When Liz laughs at me and walks away, it’s like Kate. That’s exactly how I feel.”
Colleen Conrad
Jon announced his relationship with nurse practitioner Colleen Conrad in mid-2014. The pair dated for seven years until their split in August 2021, four months after Conrad was diagnosed with breast cancer. “We had ongoing issues previous to our breakup and previous to her diagnosis, so we had trouble in the relationship for a long time and didn’t really want any stress during her treatment,” Jon said on The Dr. Oz Show. “So we thought it was best that we just stop our relationship and work on our friendship and get her through her treatment.”
Stephanie Lebo
Jon and Lebo went public with their relationship in August 2023 when they told The U.S. Sun they had begun dating after his split from Conrad. “He had ordered me a creme brûlée cheesecake, so it was waiting for me when I arrived, which is super sweet, but I don’t like cheese, so that was kind of funny,” Lebo told the outlet of their first date.
Lebo added that the pair bonded over their past relationships. “We have so much in common because we have both been with people who are not the best for us, but we wouldn’t appreciate what we have together if it wasn’t for those experiences,” she explained.
Jon and Lebo announced their engagement in December 2024. He later told Entertainment Tonight that he “would definitely” invite his estranged kids to their wedding.
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