Speaking to Heidi Montag on the Monday, April 11, episode of her “Whine Down” podcast, the country singer, 39, told The Hills alum, 36, that the first time they actually met was when Kramer was set up on a date with Jenner, 39. The podcast host and the Princes of Malibu alum went on a double dinner date with Montag and her now-husband Spencer Pratt at an L.A. nightclub around 2007.
Kramer joked about the awkward evening, calling her time with Jenner the “worst blind date ever.”
The “absolute worst,” the “Why Ya Wanna” singer emphasized, noting that the two weren’t “vibing at all” and she left in disgust — but not before accidentally walking into a mirror.
“He said something to me and I was like, ‘Ugh, I’m leaving,’” Kramer recalled, laughing while recalling her next move. “I go marching toward the exit sign … little did I know … it was the reflection [of the exit sign] in the mirror, so I slam right into the mirror.”
Fortunately for both Jenner and Kramer, the two have since long moved on romantically since their uncomfortable date.
The “Voices” singer, who had already wed and divorced first husband Michael Gambino in the early 2000s before she met the reality star, later went on to tie the knot twice more. She was married to actor Johnathon Schaech from 2010 to 2011 and former NFL star Mike Caussin from 2015 to 2021. (Kramer and Caussin, 36, share 7-year-old daughter Jolie and 4-year-old son Jace.)
Kramer and Caussin’s rocky romance played out in the public eye for years before the Michigan native finally called it quits with the former football tight end, who admitted to cheating on her multiple times throughout their marriage. Despite seeking treatment for his sex addiction, he relapsed multiple times.
“I’ve fought y’all. I’ve loved hard. I’ve forgiven. I’ve put the work in. I’ve given everything I have, and now I have nothing else to give. I just can’t fight any longer. It’s time to heal,” Kramer shared via Instagram in April 2021, announcing her and Caussin’s split. “Thank you for all the love, heart, and support, in many ways you have fought on this journey alongside me, and for that I am grateful. I’ll always encourage you to continue the good fight, but you can’t fight it alone. 💔.”
After another difficult relationship with ex Ian Schinelli — the pair split in April 2022 after six months of dating — Kramer began seeing Scottish soccer coach Allan Russell, confirming their relationship in January.
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“I don’t know if this is my forever person. … But, like, I’m not going to push away love just because I’ve been hurt before. I’m going to embrace it,” the One Tree Hill alum shared on her podcast at the time. “I’m going to have fun. And if it doesn’t work out, well, you know what? I’m gonna learn a lot of lessons. And I had a lot of fun along the way.”
Russell, 42, seemingly met Kramer’s children for the first time over Easter weekend, with the actress sharing several snaps of her beau on Saturday, April 8, and Sunday, April 9, at events with the kids.