How Jon Gosselin Found Lasting Love With Stephanie Lebo

by

For years, Jon Gosselin was wary of adding to his household.

I’ve been following Jon Gosselin for a while now, and it’s been tough to watch him navigate life after his divorce from Kate back in 2009. He recently opened up to TopMob News in April 2024, and honestly, it really explained a lot. He said he’s dated a few people, but dealing with PTSD and struggling to trust anyone has made it incredibly hard for him to build a real, lasting relationship. It’s heartbreaking, but I admire his honesty about it.

Until the 48-year-old met Stephanie Lebo, that is.

Jon described the research and development specialist as his “best friend,” saying he felt comfortable sharing anything with her.

“It’s very relieving,” he explained, “and then I can just go be me.”

I’m so thrilled to share some personal news! My partner, Jon, proposed last November, and we’re now busy planning our wedding for November 23rd. We couldn’t be happier and are really excited to start this new chapter together!

As Stephanie teased Feb. 23 on Instagram: “9 mos. ‘til I’m officially a Gosselin.”

It’s hard to ignore the reality TV connections that come with her last name, but the 38-year-old didn’t seem too bothered. Her mother, though, warned her to be careful.

Stephanie shared with Entertainment Tonight in August 2023 that her mom was shocked when she told her she was dating him. However, he quickly won her mother over, and now Stephanie jokes that her mom knows more about their relationship than she does – he speaks with her daily!

Seven months before proposing, Jon shared with TopMob that both their mothers were constantly asking about an engagement. He explained he kept telling them to give him space and that they would find out when the time was right.

Sure enough, the couple’s respective parents were on hand to watch Jon get down on one knee.

She said yes! Stephanie shared a picture of the beautiful diamond ring he gave her when he proposed. The proposal happened in a private room at Willoughby’s on Park, her favorite restaurant in Wyomissing, Pennsylvania.

And Jon isn’t just adding a plus-one for life to the equation.

Stephanie has a 14-year-old daughter named Giulianna from a previous relationship. Her husband, Jon, already had a large family: 25-year-old twins Mady and Cara, and 21-year-old sextuplets Alexis, Hannah, Aaden, Collin, Leah, and Joel. Jon has joked that Stephanie’s daughter feels like another child to him, bringing his total to nine.

Stephanie shared with ET that she’s finally getting some much-needed support. She feels confident about her future, explaining that even when they’re both exhausted, this person always goes the extra mile to help her out.

And she loves Jon, she continued, “because he’s genuine.”

Stephanie also pointed out that they rarely bother each other, and Jon agreed, saying they don’t fight often.

Jon admitted that adjusting to living together after June 2023 wasn’t always easy. He told OK! magazine that many of their early disagreements revolved around household chores and getting their kids to help out. He emphasized that life isn’t perfect and wanted to be honest about that.

With Stephanie around, things feel much more stable. She jokingly told ET she refuses to leave the house, even suggesting that if they were to split up, he could simply move into the fully furnished basement with a bar.

Stephanie and he connected at a friend’s barbecue in August 2021, and she actually messaged him first on social media afterward. Shortly after that, he spontaneously invited her for a drink. She went straight from the gym, still sweaty and with her natural curly hair and no makeup, and she believes he really liked her just as she was.

Jon said they began spending a lot of time together, but they didn’t officially announce their relationship until 2023. They just wanted to keep things private at first.

“All our friends and family knew we were together,” he said. “Our kids, all that stuff.”

Stephanie once pretended to be friends with his daughter, Hannah, to avoid anyone discovering their relationship before they were ready.

She explained that it hadn’t been difficult to simply tell him she was a mature student, and that he’d been respectful of her boundaries, acknowledging it was a lot to process. She and Jon had both spent years focusing on others, she added, and she wasn’t sure what would come of this new connection.

As it turned out, it’s going all the way to the altar.

Jon’s children, Hannah and Collin, fully supported the relationship. In December 2024, Stephanie told ET that Jon’s son sent her a touching message, calling her “the glue” that holds their family together.

Although Jon’s future wife hadn’t yet met his six children face-to-face due to a family rift, he shared in July 2024 that Stephanie had been communicating with both his children and his former spouse.

He mentioned on The Domenick Nati Show that Steph has spoken with Kate and his other children, primarily through FaceTime and using Hannah’s phone. He indicated that everything appears to be going well.

Jon admitted it could be simpler for everyone involved if they spoke with someone he already knows and trusts as an intermediary.

He said his ex-wife wanted to meet Stephanie because Kate views this as a serious, potentially lifelong relationship, and she likely wanted to understand who was impacting their children.

Last December, Jon told Entertainment Tonight that he planned to invite all of his children to the wedding, even those he wasn’t currently close to, saying he always wants them to feel welcome.

Before their dad says “I do” again, see all eight Gosselin kids through the years:

As a lifestyle expert, I’m always fascinated by families, and I was so happy to see Kate share photos celebrating her four of her six children – Alexis, Aaden, Leah, and Joel – turning the big 2-1 on May 10th, 2025! Hannah and Collin were also celebrating, of course, marking a huge milestone for all six of them.

Hannah celebrated her birthday with her dad and his fiancée Stephanie Lebo.

Okay, so Mother’s Day 2024 was EVERYTHING. It was just two days after my absolute favorite family’s sextuplets turned twenty, and Kate posted the sweetest tribute to the four who still live with her – Alexis, Aaden, Joel, and Leah. I seriously can’t get enough of them, and seeing that post just made my day! It feels like I’ve watched them grow up, and I’m so happy she acknowledged them all.

She celebrated her children turning twenty with a heartfelt Instagram post: “No more teenagers in the house! Happy 20th birthday to my babies – I love you both!” She jokingly added, “Who feels old? I certainly do!” along with the hashtags #20yearsold and #ItsaPICKLE.

Hannah shared new pics of herself on her and the other sextuplet’s 20th birthday.

On to the next chapter! The sextuplet graduated from high school in 2023.

Jon posted a photo of his sextuplets, Collin and Hannah, graduating high school in 2023. They had been living with him for several years prior to the graduation.

Kate appeared with twin Mady and Cara in New York City in this 2019 pic.

In 2022, Jon posted on Instagram to celebrate his child’s 18th birthday, writing, “Today we’re shouting it from the rooftops – happy birthday! I love you. Love, Dad.”

Kate recently celebrated her children turning fifteen! The day was filled with festivities, starting with a surprise gift before school at 6:30 am. Reflecting on the milestone in 2019, she expressed how quickly time has flown and how proud she is of the wonderful people her ‘babies’ are becoming as they grow into young adults. She’s amazed by them every day and loves seeing their positive qualities develop.

In a 2018 Instagram post, Kate expressed feeling like summer vacation flew by, saying, ‘This was yesterday! Feels like school never ended…and they’re already back!’ She added the hashtags #SeniorYear, #EighthGrade, and #ProudMom.

 

Jon Gosselin wished his twins, Hannah and Collin, a happy 15th birthday on Instagram, also sending wishes to Aaden, Joel, Alexis, and Leah. He expressed how quickly time has passed and shared his love for all of them, hoping they have a wonderful birthday and celebrations this weekend. He signed the message, ‘Love always, Dad’.

Kate shared a funny story about her daughters constantly counting down to their 14th birthdays. She posted about how they recently reminded her it was only 12 days away, which she found unbelievable! She jokingly told one of her daughters, Leah, that she was too young to be turning 14, and Leah questioned if she might actually be turning 11 or 12 instead. Kate reassured them she knew how old they were, reminding them she was there when they were born, and expressed how much she loves her ‘babies’.

I still can’t believe it, but my amazing sextuplets just turned 13! Kate Gosselin shared the news on Instagram, and honestly, where did the time go? It feels like yesterday they were babies, and now they’re officially teenagers. So proud of each and every one of them!

Rewind to 2014 whenKate and her children found themselves visiting Alaska. 

In 2014, Kate took her twin daughters, Cara and Mady Gosselin, on a trip to New York City, including a visit to a Manhattan hotel.

Kate Gosselin shared a sweet Christmas memory on Instagram, posting a throwback photo from Christmas Eve 2010 when her six children were all six years old. She captioned the picture, highlighting their excited and adorable smiles, and expressing her love for them, calling them her ‘8 reasons to keep on keeping on’ and ‘true love.’

 

In October 2007, Jon and Kate Gosselin brought their eight children to New York City, and their first activity was an appearance on NBC’s Today show.

Read More

2025-11-23 14:18