A Look Back at Jon Gosselin’s Dating History

Jon Gosselin and Kate Gosselin were a master class in what not to do when you get reality TV famous. The former reality TV stars’ incredibly messy divorce in 2009 dominated headlines and has significantly impacted the relationship their eight children have with their parents and with each other. In the years since, the former pair has cycled in and out of the public eye. Jon Gosselin just stepped back into the spotlight to announce that he is, once again, a married man. Let’s take a look back at his dating history.

Jon Gosselin rose to fame when he was already married to Kate Gosselin

Jon Gosselin’s most famous and most troubling relationship was with Kate Gosselin. They met at a picnic years before they became famous, and married relatively quickly. In 2000, they welcomed twin daughters together, followed by their sextuplets four years later. In 2007, their reality TV show, Jon & Kate Plus Eight, premiered on TLC. The family became an overnight sensation.

As the series progressed, viewers raised concerns over their relationship. Fans cited clips of Kate snapping at Jon, speaking down to him, and steamrolling him. In 2009, they announced their plans to divorce. Who was actually to blame for the split has been a topic of hot debate for more than a decade. They finalized the split in late 2009 and moved on, though Jon had limited contact with most of his children following the divorce. He has claimed parental alienation. Jon Gosselin remained close to the family’s home in Pennsylvania. Kate Gosselin eventually moved to North Carolina.

Things got messy in his dating life after their split

After Jon and Kate Gosselin’s marriage devolved into tabloid fodder before imploding, he moved on quickly, though not cleanly. While Kate Gosselin didn’t really date publicly, Jon did, and it was pretty messy. Shortly after the split, he began seeing Hailey Glassman, the daughter of a plastic surgeon who treated Kate Gosselin. The short-lived romance ended in a pretty epic meltdown, complete with allegations of cheating and vandalism. He also had a short-lived romance with Kate Major, a reporter, in 2009. Major, speaking to Life & Style after the split, called Gosselin a “dirtbag” who totally “screwed” her over.

In 2012, he began dating Liz Jannetta. The duo had a tumultuous relationship that led them to appear on Couples Therapy together. In the end, the union couldn’t be saved. They split up in 2014, amid significant financial struggles. Jon Gosselin moved out of the home they shared after failing to make rent for several months. Jannette indicated that the split was not amicable.

He settled down with Colleen Conrad in 2014

After several years of truly messy dating, odd breakups, and another stint on reality TV, things got very quiet for Gosselin. He reconnected with a woman from his past named Colleen Conrad. The former flames grew up together in Pennsylvania, but they lost touch as they grew into adulthood. They reconnected in 2014 and began dating.

Conrad and Gosselin appeared to be blending their families, despite not legally marrying. Hannah Gosselin came to live with the duo first, followed by Collin Gosselin a couple of years later. While they publicly supported each other and seemed happy in their romance, they announced their split in 2021, citing growing apart as the reason. Conrad had been diagnosed with breast cancer just a few months before the split, which led to some speculation from onlookers. Conrad has remained supportive of Jon’s children despite the split, referencing Collin as recently as 2023, but she seems to keep herself out of Jon Gosselin’s public business.

He met his current wife right around the time he split from Conrad

In 2021, shortly after ending his romance with Conrad, Jon Gosselin met Stephanie Lebo. They began dating quickly and went public with their romance in late 2021. They’ve been together ever since, publicly proclaiming their love on social media starting in 2022. Things got even more serious in 2024, when they announced their engagement.

Gosselin and Lebo, who works as a research analyst in Pennsylvania, tied the knot in an intimate ceremony in November 2025. Hannah Gosselin and Collin Gosselin both attended, according to Entertainment Tonight. They are the only two of Gosselin’s eight children with whom he has a current relationship. Lebo brings a daughter into the marriage, as well.