Jon Gosselin's Complete Dating History

You probably know Jon Gosselin as the star of the reality TV show "Jon & Kate Plus 8," which first aired on TLC in 2007. The show centered around Jon and his wife Kate raising their eight children in Pennsylvania: twin girls named Cara and Madelyn, and sextuplets Alexis, Hannah, Aaden, Collin, Leah, and Joel.

Although Jon has a whopping eight children, the list of women he's dated is surprisingly even longer. Over the years, he's made a name for himself as a womanizer, making headlines for his messy divorce, cheating scandals, and tendency to date younger women (hint: there are a lot of 23-year-olds on this list). From 2009 onward, if you picked up a newspaper or read an article online, chances are you would come across a story about yet another one of Jon's new girlfriends. He is rarely single, seemingly hopping from long-term relationships to brief flings in the blink of an eye. 

From rumored affairs he's continued to deny to publicly confirmed relationships and messy breakups, we've rounded up everything you need to know about Jon Gosselin's relationship history.

Jon Gosselin met his future wife Kate Gosselin (who went by Kate Kreider back then) at a picnic in 1997. "Everything clicked. It sort of felt together like it never felt before," Gosselin said on meeting Kate (via People). "This time was different." The couple had a backyard wedding on June 12, 1999 in Pennsylvania, and began fertility treatment after Kate was diagnosed with polycystic ovary syndrome. It worked, perhaps a little too well — the couple went on to have eight children together, twins girls followed by a set of sextuplets. In August 2008, the couple renewed their vows in Maui, Hawaii.

Only a year later, allegations surfaced that Jon had been cheating on his wife with Deanna Hummel. A month later, Kate filed for divorce. "Parents of multiples have triple the divorce rate," Kate said in May 2009 (via Us Weekly). "I was thinking we were going to beat that. I don't know if I can say that anymore." The divorce was finalized in December 2009, and Kate was granted full legal custody. Things soon got messy, with reports that police had been called over a custody dispute at the children's orthodontist office. Their daughter Hannah ended up choosing to live with Jon full-time, and in 2018, he was granted full custody of their son Collin. Jon Gosselin said he feared for the safety of his other children, telling the Daily Mail, "I do know what she's capable of, whether it's mental or physical [abuse]."

In 2009, Us Weekly reported that Jon Gosselin was cheating on his wife with third-grade schoolteacher Deanna Hummel. The publication's source was Hummel's brother and roommate Jason, who said that the affair had been going on for three months. "She's a nice girl, not a homewrecker," Jason told Us Weekly. "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."

According to Jason, the couple met in January at a Pennsylvania bar. Once the affair began, Gosselin often came over to the siblings' house, where he and Deanna would "pretty much stay locked away like two teenagers," according to Jason. He also revealed details no brother should ever have to share, saying, "A lot of the time, it was pretty, um, gross listening to her, you know, um, how do I say this? The walls are thin. Let's just say that. I mean, no one wants to hear his sister having sex, let alone with a married dude who's, like, almost twice her age and who has eight kids and a maybe-crazy wife. Ick."

Both Gosselin and Hummel have denied the allegations, with Hummel explaining that her brother is a criminal on probation who cannot be trusted. "My brother is making this all up," she told People (via Today). "He has no credibility ... I can't even stomach the lies he's saying about me."

While reeling from his divorce from Kate Gosselin, Jon Gosselin began dating longtime family friend ​​Hailey Glassman. Glassman, who is 10 years Jon's junior, told People she never expected their friendship to turn into anything more. "If you had told me a few months ago, I wouldn't have believed you," she said.

Glassman denied the engagement rumors that were circulating, but it was clear the couple was in love. "We're always laughing and joking," she said. "We watch movies, play pool, and ping pong. We laugh a lot because I beat him at everything." She praised his cooking skills and added that her family adores Gosselin and thinks of him as part of the family. "They think things happen for a reason," she said.

After the breakup, Glassman told Hollywood Life what went wrong. "Jon was just compulsively lying ... constantly," she said. "He took a lot of money from me. He hurt me, and he hurt my family, which is the worst of it. I think he played the victim for so long and people were shocked when they found out Jon was the villain," she said. She also accused Jon Gosselin of trying to extort up to $100,000 from his ex-wife by threatening to call Child Protective Services, and made fun of his penis size. "He was so small I didn't think he would cheat on me," she told Steppin Out Magazine, adding, "He's hung like a nine-year-old boy" (via Us Weekly).

In 2009, Jon Gosselin's 23-year-old nanny Stephanie Santoro alleged that she had a relationship with him shortly after he filed for divorce from Kate Gosselin. In an exclusive interview with In Touch Magazine, Santoro said it started when he invited her to hang out in his hot tub, and back massages led to kissing. "At one point he said, '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,'" she said (via Huffington Post).

The single mother explained that the two quickly became very close. "We would lie in bed and talk about the future. He would say how he wanted to make sure my daughter and I would always be okay, and how he would take care of me," she said. Santoro claimed they slept together nine times while Jon Gosselin's children were sleeping. When asked whether Jon was still seeing Hailey Glassman at the time, Santoro said, "I don't think he has ever been apart from Hailey, but he has cheated on Hailey. I know they've broken up before. I didn't know their current status. We talked about it, and he had told me that things were very weird and strange and he would explain it to me, but he didn't want to hurt me in the process." 

However, Jon's lawyer, Mark J. Heller, refuted Santoro's allegations, accusing the tabloids of trying to boost their sales by publishing unverified, sensationalist news.

Former Star reporter Kate Major claimed she had a three-day whirlwind romance with Jon Gosselin in July 2009, shortly after he filed for divorce. At the time, Gosselin was dating Hailey Glassman but allegedly promised Major he was going to Massachusetts to end the relationship. "He tried to two-time both of us," Major told E! News. "He wasn't honest with Hailey. He needs to man up and tell the truth. I'm not going to be the other woman." Major claimed the couple had plans to travel and live together, while Gosselin denied the allegations. "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," Major said in an interview with "Showbiz Tonight" (via Today).

According to Major, she had to resign from Star magazine once she began her romance with Gosselin. "I was with the person I was reporting on ... It was a huge conflict of interest," Major said. "He's the one who actually told me to quit my job."

Despite the fallout, Major has no regrets coming forward with her story. "It's been a nightmare. I did not want to have to do this...I have to speak. I did not want to have to sell him out but when he makes me look like a liar, a fool and an idiot. I have to speak out," she told E! News.

In January 2010, it was reported that Jon Gosselin had a new girlfriend: 25-year-old law student Morgan Christie. The couple met while snowboarding in Utah, where Christie's parents live. "She grew up very privileged, tons of money," a source told People. His new love was originally from Greenwich, Connecticut and attended Emory University.

The relationship was confirmed when the couple was spotted attending the Sundance Film Festival together later that month. Witnesses said Gosselin and Christie couldn't keep their hands off each other. "Tons of PDA, holding hands, kissing," a source told Us Weekly. "Anyone who saw him remarked how inappropriate it was." Another source told People that "Morgan was talking to some producers about possibly doing something" and that "Jon was in a great mood!"

However, the relationship didn't last long, and the couple split after only two months together. According to a source, Christie was the one who called it quits. "He's a mess and feels like a loser," they said (via Us Weekly).

Jon Gosselin doesn't stay single long. After his fling with Morgan Christie, he had a two-year relationship with a woman named Ellen Ross.  And shortly after their breakup, he began dating divorced mother-of-three Liz Jannetta in 2012. The relationship lasted about two years, during which they appeared in Season 4 of VH1's reality show "Couple's Therapy." "When I first met Liz, the thing that drew me to her was how honest she was. Her smile brightens up a room," he said when introducing her on the show (via Radar Online).

However, the breakup would be no surprise to anyone who watched the show. One of their most explosive and bizarre arguments came after Jannetta walked in on Gosselin supposedly in a sexual act (albeit by himself). Gosselin professed his innocence, but Jannetta didn't believe him. She swore at him before leaving the room in a huff. "It's humiliating ... You are such a jerk. I'm like, ready to throw up actually," she said (via Us Weekly). Gosselin tried to explain himself, saying, "I wasn't doing anything, I swear to God." Jannetta laughed and accused him of paying the victim yet again.

The split came in 2014 after Gosselin compared Jannetta to his ex-wife Kate. "When Liz laughs at me and walks away, it's like Kate," he said on the episode of "Couple's Therapy" (via Us Weekly). "That's exactly how I feel." Both Gosselin and Jannetta also admitted to cheating on each other.

In 2014, Jon Gosselin began dating nurse practitioner Colleen Conrad, whom he's known since childhood. "I've known Colleen my whole life," he told OK!. "We grew up three blocks from each other. Her sister used to babysit me."

The couple dated for about seven years, marking Gosselin's longest relationship since his marriage, before breaking up in August 2021. The split came four months after Conrad was diagnosed with breast cancer. She underwent a single mastectomy on her right breast, followed by a DIEP Flap procedure. "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," Gosselin said on "The Dr. Oz Show" (via People). "So we thought it was best that we just stop our relationship and work on our friendship and get her through her treatment." He maintains her diagnosis wasn't the reason for the split. "I'll always love Colleen and we're friends and it wasn't because of cancer," he added.

A source told In Touch that the couple wanted desperately to make it work. "They tried it all: couples therapy, family counseling, everything possible," they said. Despite the breakup, Gosselin will still support Conrad during her treatments. "Jon wishes her the best and will continue to help her through her cancer battle," the source said. "The kids love Colleen and will continue to be in her life."

A few months after his breakup with Colleen Conrad, Jon Gosselin started dating Stephanie Lebo. The couple managed to keep their relationship under wraps for two years, only going public with their romance in August 2023 in an exclusive interview with The U.S. Sun.

The pair met at a mutual friend's barbecue, and he took her to a bistro for their first date. "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 U.S. Sun. The couple fell for each other very quickly. "We are really happy and in love," said Gosselin. "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.'"

Lebo says they bonded over their shared relationship trauma. "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," Lebo told The U.S. Sun. After a string of failed relationships, it looks like Gosselin has finally found the one. "I feel it's taken 19 years to find Steph. All the trials and tribulations, the heartbreak, the fighting, and worrying about who is going to talk about me to the press, then finally I meet Steph," he said.