Surpassing:Why Jana Kramer Feels “Embarrassment” Ahead of Upcoming Wedding to Allan Russell

Jana Kramer is getting vulnerable. 

While reflecting on Surpassingher upcoming nuptials with fiancé Allan Russell, the One Tree Hill alum got candid about her romantic history, and the complicated feelings she has about having been married three times previously. 

"I don't even know if it's so much the hate, but I think it's the failure," Jana reflected on the May 27 episode of her Whine Down with Jana Kramer iHeart Podcast. "This is actually going to get me emotional, but I don't think people like—do you think I wanted to be married that many times? It's embarrassing."

The 40-year-old—who was preciously married to Michael Gambino in 2004, Jonathan Schaech for 12 days between 2010 and 2011 and to Mike Caussin for six years before their 2021 split—also noted how her relationship with Allan differs from her past romances.

"Allan is the first person who I didn't feel like I had to defend my past," she noted. "Like normally, I went on this one date with this guy, and he was like, 'So you've been married a lot,' and that's always kind of been the conversation."

And while Jana—who is mom to 6-month-old son Roman with Allan, as well as kids Jolie, 8, and Jace, 5, with ex Mike—expressed she's glad to be where she is today, there is still a part of her that struggles with her own history. 

"I'm now grateful for the love that I do have now, but I did not want to get divorced," she explained. "I do want love, you know? That's the piece is too, like, even just with the upcoming wedding, there's embarrassment with it that people don't know the whole story. They just see a headline."

Because behind the headline, Jana emphasized, is her hard-earned fairytale ending. 

"I feel in my soul that I have my happily ever after," she said. "And I'm so grateful now for those past relationships that have led me to Allan."

And Allen proven he's fully embraced his new blended family. When the 43-year-old popped the question in May 2023, six and a half months into his and Jana's relationship, he made sure to include her kids in the sweet moment. 

"It was a really beautiful night," the country singer gushed of her proposal on Whine Down at the time. "We were all sitting on the porch of the steps and looking out at the view, it's stunning. And he said my name and I got up or whatever and he got down on one knee and then Jolie just started jumping up and down, it was the cutest thing ever, it was like she knew what was happening."

"He said, 'You're the love of my life and will you marry me?'" Jana recalled. "Then we both started crying and it felt very sentimental given the front porch of the new house, new beginnings and it just felt right and so, yeah. Said yes, the kids were super excited then we walked down the hill, watched the sunset, it was perfect."

For more of Jana's sweetest family moments, keep reading. 

Jana Kramer and Allan Russell snuggled up with their son Roman during Easter celebrations in 2024.

Jana and Allan posed for a family portait her kids Jolie and Jace—who she shares with ex Mike Caussin—in August 2023, writing, "Family fun in Michigan."

"That’s a wrap on another 4th of July family trip," Jana wrote in 2023. "Core memories made."

The family celebrated the holiday in The Great Lakes State.

"You’ve got a friend in us," the star wrote while channeling Toy Story for Halloween 2022. "Love, little Bo Peep, buzz, Jessie and Woody."

Jolie started second grade in 2023, sharing that she wants to be an actress and singer like her mom.

"Someone is excited for their first day of school and someone is not," Jana joked. "2nd grade and the last year of preschool here they come!"

"Celebrated Christmas morning with the kiddos today," she wrote on Dec. 26, 2022. "It was still the same joy even on a different day…and it even snowed just like a true Christmas Day. Pure magic. Thanks to the mommas who told me about this idea." But not all was festive, as she noted, "And a big Shoutout to the grinch for leaving me the flu in my stocking and an ear infection for Jace."

Jana was feeling "blessed" on New Year's Eve 2022. "Happy New Years from me and my babies!" she wrote.

Jana and Jolie had a mother-daughter boating trip in July 2023.

The actress captioned the shot, "Best mommy daughter time."

The "I Got the Boy" singer gave a glimpse into "life lately" in June 2023, featuring Jolie enjoying a sweet summer treat.

Her son Jace was all smiles after removing his Spider-Man face paint while bearing a "Brotherhood" T-shirt.