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Jon Gosselin started making waves in the television industry after he starred inJon & Kate Plus 8alongside his then-wife Kate Gosselin. The duo met each other during a company picnic in 1997 after which sparks instantly flew between them and they got married two years later in 1999. A year later in 2000, they welcomed their twin daughters and in 2004 they were blessed with sextuplets, making them a big family of ten.

The reality show was released in 2007 and heavily featured their day-to-day life, with eight kids. While everything looked normal on the outside, everyone was left shocked when Kate filed for divorce. The show was also later renamedKate Plus 8and focused on her as a divorced mother raising eight kids. While their divorce was messy, they soon found a common ground and now Jon had moved on to a new chapter of his life.
He recently got engaged to Stephanie Lebo who he’s dating for the last three years. In this article, let’s take a closer look at what she does, where they met, and all about Jon Gosselin’s past relationships.

What Do We Know About Jon Gosselin’s Fiancé Stephanie Lebo?
After a lot of media attention, Jon Gosselin is finally ready to move on with his life after his engagement with Stephanie Lebo. The duo has been dating since 2021 and turned a new page in their lives and fans are absolutely thrilled to see Gosselin happy again. In the midst of all the scrutiny, many want to know more about his soon-to-be wife who’s also a skilled professional.
Stephanie Lebo works as an R&D chemist and a cosmetologist, while also balancing her love for beauty on the side. In this year itself, she also began working as a lash technician and started sharing her work on Instagram. Besides her professional endeavors, she also has a daughter from a previous relationship and keeps a rather low profile on social media.

But she does share bits and pieces of her professional accomplishments with her fans. On the kids front, while Lebo has a daughter, Gosselin also shares eight kids with ex-wife Kate Gosselin. Things between him and his kids have also not been good since his divorce as he’s now estranged from six of them.
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Gosselin does have a closer bond with his two children Hannah and Collin who also reside with him in Pennsylvania. Despite this, he did add thatLebo has met his kidsthrough FaceTime using Hannah’s phone. He added:
I know that Steph has talked to Kate, and I know that Steph has talked to my other kids. Just, like, through FaceTime and Hannah’s phone and stuff. Everything seems copacetic.My other kids haven’t talked to me though. Maybe it’s just easier to talk with someone who is with me but not me.

He continued:
I feel like I’m a pretty open person since I do eight million interviews and people always ask me stuff, but I just feel that maybe under the scrutiny of everything that transpired, that it might just be easier for them to talk to a third party individual that’s totally integrated into my life.
Talking about Kate and Stephanie’s equation he added that they’ve“just said hi”to each other. Also, his ex-wife does understand that his relationship with Lebo is a long-term thing and that she just wanted to know the person who’s going to be around her kids.

Jos Gosselin and Stephanie Lebo’s Engagement and How Did They Meet?
More than a decade after his high-profile divorce from Kate Gosselin, Jon Gosselin has gotten engaged for a second time. He got down on one knee and proposed to his girlfriend of three years Stephanie Lebo on Thanksgiving Day. The happy duo shared the news with a joint point viaEntertainment Tonight. The television personality popped the question at Lebo’s favorite restaurant Willoughby’s on Park in Wyomissing Pennsylvania.
The romantic proposal also had both of their parents in attendance, making the moment even more special for her. Lebo’s father who was present at the venue got deeply emotional and“cried his heart out and whispered in her ear. “He told her how long he had been waiting for this day and at one point he thought that maybe this day was“never going to happen”for her.
While the proposal was definitely moving, how they met also has an interesting backstory of its own. In an interview viaThe Sun, Jon Gosselin added that the duo crossed paths for the first time in 2021 at a“backyard barbecue at a mutual friend Dean’s house.”This was after his break-up with longtime girlfriend Collen Conrad, and he was single for a few months.
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On meeting Lebo he added,“It was a hillbilly thing, we let fireworks off, it was fun.”While the engaged couple look very much in love, Gosselin was previously married to Kate Gosselin (formerly Kreider). The duo then went through a very publicized and messy divorce and were married for a decade (1999-2009).
Jon Gosselin’s Relationships and Tumultuous Marriage with Kate Gosselin
The reality showJon & Kate Plus 8that aired in 2007 brought huge media attention to Jon Gosselin and his personal life. While most of it was in good light, things started to shake up for him after his decade-long marriage with Kate Gosselin came crashing down in 2009. Not only that butreports of his infidelitywith a woman named Deanna Hummel also started making waves in the media.
In the midst of this, the former couple had a very messy divorce with Kate getting full custody of their kids, though Jon later got custody of Hannah and Collin. After his divorce, his first relationship was withHailey Glassmanwho was also 10 years his junior. They dated for a brief period but according to Glassman they eventually broke up due to hislying and manipulation.
After this, he was also linked to his kid’s nannyStephanie Santoroin 2009, with her claiming that their relationship began after he filed for divorce from Kate. She also made several wild confessions and accusations which Gosselin’s lawyer refuted. After settling this, he was also linked to Star magazinereporter Kate Major in 2009which caused further complications as at the time he was still with Glassman.
But Major revealed that he had promised her that he would end his relationship with Glassman to be with her. This love triangle created a lot of headlines and his relationship with Major only lasted for a few days. In 2010, after all the drama hemoved on to Morgan Christiewho was a law student at the time, and met him while snowboarding. But they dated for two months after which he starteddating Liz Jannetta, a divorced mother of three.
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This relationship lasted for two years and was also featured inVH1’s Couple Therapy.After Jannetta, he started datingColleen Conrada nurse he had known since childhood. The duo was together for seven long years making it his longest relationship since his divorce.
But they broke up in 2021 after Conrad was diagnosed with breast cancer, and after her diagnosis, the duo decided to stay friends instead. A couple of months later he met Stephanie Lebo, and they recently got engaged after dating for three years.
Sakshi Singh
Articles Published :1434
Sakshi Singh has written over 1,300 entertainment articles, mostly about Netflix shows and reality TV. She’s spent the last two years covering everything from surprise engagements to shocking eliminations and previously wrote for Essentially Sports in their Netflix Junkie division. A self-proclaimed reality TV addict, Sakshi has watched all 48 seasons of Survivor and never misses a new dating or competition series. She loves watching how strangers meet, fall in love, team up, or betray each other - it’s the mix of strategy and drama that keeps her hooked. When she’s not glued to a reality show, she’s usually watching a crime thriller or tracking the next big streaming hit.