What to Know
At the end of 2025, baseball player and internet personality Jackson Olson took to social media to announce that he was looking for a girlfriend. He jokingly called the viral video his “official 2026 boyfriend application,” and apparently, the audition of sorts actually worked. On April 21, Jackson and his new girlfriend both made their relationship Instagram official—and it just so happens that his girlfriend is retired Wheel of Fortune host Pat Sajak’s daughter, Maggie Sajak.
Maggie, 31, works as the social media correspondent for Wheel of Fortune and Celebrity Wheel of Fortune. Meanwhile, Jackson plays baseball for the Savannah Bananas. Their relationship announcement feels pretty on-brand.
On Instagram, they announced that applications are officially closed.
@jacksonolson_ Not sure if this will help me or hurt me 😭 #single #dating ♬ original sound – thesavbananas
Because, yes, Jackson really pitched himself as a potential boyfriend to the entire internet. In December 2025, he shared a video on TikTok, in which he explained that he had been single for five years and was hoping to find love. He then shared several qualities that would make him a good boyfriend (or, at least, would show people whether he would be the right boyfriend for them).
First, he wrote, “I dance on baseball fields for a living.” He also made his love for Disney very clear, as he told all the prospective girlfriends watching that his ideal vacation was to a Disney theme park (and Epcot is his favorite bar).
He admitted to having Peter Pan syndrome, playing with Legos as an adult, and enjoying Taylor Swift and musicals. Clearly, he was really committed to finding his perfect match, even though he wasn’t actually sure that creating that particular application video was a good idea. “Not sure if this will help me or hurt me 😭” he captioned the post.
But it clearly worked out for him.
Maggie and Jackson’s joint Instagram post announcing their relationship clearly referenced the application video. For one, the picture they posted showed them at Disney together, with Maggie sporting Minnie Mouse ears. Then, the caption simply read, “Applications closed✅”
People in the comments were happy for the couple—and several people referenced Wheel of Fortune. “I love this for you! She’s so pretty!” one of Jackson’s followers commented. Is she Pat’s daughter?” Someone else wrote, “Clearly your wheel of fortune landed on the right spot.”
“Ok he spun the million dollar wedge and won 🏆” another commenter added.
Maggie has been working on “Wheel of Fortune” since 2021.
So, in that way, she’s already following in her dad’s footsteps. However, after Pat retired, some fans of the show wondered if Maggie would eventually become a host instead of a social media correspondent. Back in 2024, an insider told The U.S. Sun that Sony had considered Maggie as an option in the event that a new host is needed for the show.
“Maggie has positioned herself to help out if there’s a hosting vacancy, and the franchise is in her blood and her appreciation for the world of Wheel of Fortune is genuine,” the source said at the time.
Maggie has said that “the show means so much to me and to my family, so we’re always gonna want that to stay so special and it will.” However, she appears to have other ambitions as well, given that she went to law school.
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