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." Jon Gosselin Reveals He's Been Dating His Secret Girlfriend For 2 Years 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 Kate Gosselin Noel Vasquez/Getty Images 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 celebr