Jana Kramer Recalls ‘Sweetheart’ Jason Oppenheim Asking Her Out on a Date

Jana Kramer almost rode off into the sunset with Jason Oppenheim.

During the Wednesday, November 26, episode of iHeartRadio’s “Whine Down” podcast, the former One Tree Hill star was asked during a Q&A if she has experienced any “unexpectedly flirty” guests.

“I don’t think anyone’s been inappropriate,” Kramer, 41, said.

Cohost Kristen Brust added, “We don’t really have a lot of dudes, though.”

A producer, however, quickly reminded Kramer of the chemistry she had with Oppenheim, 48.

“He flirts with everyone. I love you Jason, but he flirts,” Kramer said about the Selling Sunset real estate agent. “He’s a sweetheart. But he did ask me out, that’s true. [I] blinked that out. He did. It was on air.”

Before listeners’ jaws dropped, Kramer explained that the Oppenheim Group realtor is “so respectful.”

And while nothing romantic came out of the podcast interaction, they were able to enjoy a friendly meal together.

“We even had lunch with a friend,” she said. “I was introducing him to our realtor friend, and he’s such a sweet man.”

For the record, Kramer is happily married to Allan Russell, while Oppenheim is currently dating fellow real estate agent Jessica Vargas.

During the podcast, the “I Got the Boy” singer joked that her flirty days are long gone.

“I used to be flirty, but now, I mean, I’m like the farthest thing from,” she shared. “Our intentions in the moment weren’t that at all. And some intentions when I was flirty was because I wanted to fill that ‘love me, choose me’ terrible dialogue in my brain.”

Before marrying Russell, 44, Kramer was previously married to Mike Caussin. While the exes — who share Jolie, 9, and Jace, 6 — weren’t always in a good space after the split, both parties have found themselves in a cordial spot.

“I’m incredibly grateful for where @kramergirl and I are at in our relationship,” Caussin, 38, wrote via Instagram in November 2023. “We have both found a way to flourish for ourselves and more importantly the kids. The fact that she has found someone like @superiorstriker only adds to my level of gratitude towards the entire situation. Jolie and Jace have the gift of three parents that love them and will do anything to protect them. As a father, what more could I ask for?”

In a separate April 2023 interview with Us Weekly, Kramer added, “I think we’re doing a really great job and I’m really proud of us for the way that we’ve coparented and how we have just kinda let our own story lines go and just focus on the kids. … I want him to be so happy. I wanna be happy. I just, I want everyone to be happy.”

With Thanksgiving here, Kramer took a moment to express gratitude for the life she built with her family. (She also shares Roman, 2, with Russell.)

“Thankful today and always,” she wrote via Instagram on Thursday, November 27, with new family photos. “Wishing you all a beautiful Thanksgiving 🤎.”