Who is Jackson Olson Dating? Meet the Savannah Bananas Player's Famous Girlfriend! | Just Jared

Jackson Olson is trading the baseball diamond for the ballroom!

The 28-year-old Savannah Bananas player will be competing on season 35 of Dancing with the Stars which premieres TONIGHT (Tuesday, September 15) on ABC and Disney+. He’s been partnered up with pro dancer Emma Slater.

While watching the season premiere, you may be wondering if Jackson is single or if he’s in a relationship. We can confirm that Jackson is happily off the market and has a famous girlfriend!

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Who is Jackson Olson dating?

Back in April 2026, Jackson confirmed that he is dating Maggie Sajak. For those who don’t know, Maggie, 31, is the daughter of former Wheel of Fortune host Pat Sajak and she has served as the social correspondent for the ABC game show for several years now.

Jackson hard-launched his relationship with Maggie as they posed together in front of Cinderella’s Castle at Disney World.

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How did Jackson and Maggie meet?

In a recent interview, Jackson revealed that he and Maggie met in person for the first time in October 2025 at a Dodgers playoff game, a month after they started following each other on Instagram.

As Jackson shared photos on his Instagram Story at the game, Maggie wound up being in the background of one of the photos.

After discovering they were in the same place, they exchanged messages and waved to each other. Maggie then joined Jackson for a drink before they returned to their separate seats.

He also discussed the practical side of their romance. At the time, they were living on opposite sides of the country, and he said making the relationship work meant planning visits and setting aside time together. Maggie had attended his games, too, which initially gave him an extra reason to feel nervous about his performance.

Dancing with the Stars kicks off it 35th season with a two-night premiere starting on Tuesday, September 15. It will air on ABC and Disney+, with episodes available the following day on Hulu. See all of the stars competing on the new season here!

Posted To:Dating History Jackson Olson Maggie Sajak