Maggie Sajak and Jackson Olson are quickly becoming one of those celebrity couples everyone wants to know more about. Maggie, the daughter of former Wheel of Fortune host Pat Sajak and a social correspondent for the show, met Olson, a Savannah Bananas baseball star and current Dancing With the Stars season 35 contestant, at an October 2024 Los Angeles Dodgers playoff game. The two had already been following each other on social media, so when they crossed paths in person, the connection was immediate.
They confirmed their relationship in April 2026 with an Instagram post in front of Cinderella Castle at Disney World, which is about as fairy-tale as a hard launch gets. By May 2026, Olson had met Pat Sajak, and he described the legendary host simply as“a great guy.”Since then, Maggie has been a constant presence in the DWTS audience, supporting Olson and his pro partner Emma Slater throughout the season while the pair navigate a long-distance relationship between her work and his baseball and dancing commitments.
Olson has even teased that Pat Sajak might eventually attend a Dancing With the Stars taping, which would be a crossover moment fans of both shows would absolutely lose it over. Between the ballpark moments, the family introductions, and the weekly ballroom support, this couple has built a timeline that reads like a rom-com script. What’s your favorite celebrity relationship moment of the year so far? Let us know in the comments.
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Local Lawton
Local Lawton is a contributor to LocalBeat, covering local news and community stories.