DWTS Premiere: Maggie Sajak Supports Boyfriend Jackson Olson in the Ballroom

Jackson Olson is hitting the dance floor on Season 35 ofDancing With the Stars, and he has the ultimate support system in girlfriend Maggie Sajak amid his journey in the dance competition. Olson performed for the first time during the September 15 premiere, and Sajak was in attendance to show him some love.

Before the show, she revealed on her Instagram Story that she was “so excited” to go support Olson in the ballroom. She later posted a selfie to her Story from the audience (she posed with two friends) and captioned it, “Go Jackson!!!”

For his first dance, Olson scored a 15/30. He danced a cha-cha to “Wannabe” by the Spice Girls.

The couple hard-launched their romance in April on Instagram with a post from Disneyland. “Applications closed,” they captioned the joint post.

Maggie Sajak/Instagram

The two recently shared more information about how they met, noting that it began after they followed each other on Instagram in September 2025. The following month, they were both at a Los Angeles Dodgers game and Sajak was in the background of one of the photos Olson posted.

“Someone DM’d someone, doesn’t matter who, and the other person DM’ed back,” Sajak revealed. “We waved at each other.” They met up and had a drink together before returning to their respective seats. The relationship began after that.

Sajak is a social media correspondent forWheel of Fortune, the game show that was previously hosted by her father, Pat Sajak, while Olson is a baseball player for the Savannah Bananas. Now, he’s also addingDWTS to his resume. Olson is partnered with Emma Slater for the show.

Ahead of the premiere, Sajak was already showing her man major love. “Cha cha-ing right into my heart!” she captioned a September 13 post. “Couldn’t be more proud of @jacksonolson_ and I’m SO excited to watch him and @theemmaslater CRUSH it on Tuesday.”

Premiere week is a big one for the contestants, as one male will be eliminated at the end of September 15 episode, and a female will be going home at the end of the September 16 episode. We know who Sajak will be voting for!

Dancing With the Stars, Premiere Night 2, Wednesday, September 16, 8/7c, ABC and Disney+