Jackson Olson, the Savannah Bananas second baseman currently competing on season 35 of Dancing With the Stars, has been in a public relationship with Maggie Sajak since April 2026, according to Yahoo News. Maggie Sajak, 31, is the daughter of Pat Sajak, who hosted Wheel of Fortune from 1981 until his retirement, and she now works on the show herself as a social media correspondent.
The pairing has drawn attention on both sides: Olson brings a large following from baseball and content creation, while Sajak carries one of American television's most recognizable family names. Their crossover into reality television illustrates how personal branding now moves fluidly across sports, game shows, and social platforms.
Who is Maggie Sajak?
Maggie Sajak was born in 1995, more than a decade after her father began hosting Wheel of Fortune in 1981. She appeared on the program at age 1 and returned in 2020 as a guest letter toucher. In 2021 she joined the show full-time as its social media correspondent, producing behind-the-scenes content, player and celebrity interviews, and previews of upcoming episodes.
Her portfolio is unusually broad for a television personality. Sajak attended Princeton University, completed a postgraduate program at Columbia University, and earned her law degree at Georgetown University. She is a licensed attorney in California.
“The Wheel of Fortune staff and crew have always been like an extended family and I'm thrilled to be working with them,” Sajak said when she took the full-time role, per People. “It's a real privilege to be able to treat the show's longtime viewers to a look at what goes on when the cameras aren't rolling. Plus, I get to use the carpool lane with my father!”
On May 10, 2023, she made her hosting debut on Wheel of Fortune, filling in for Vanna White when the longtime co-host became a contestant on the show.
A brief country music career
Before law and television, Sajak tried music. At 16 she launched a short-lived country music career, releasing a first single titled “First Kiss,” with a music video directed by Trey Fanjoy and filmed in Nashville. Follow-up singles included “Wild Boy,” “Live Out Loud,” and “If I Was Gonna Go.”
“It's always been a dream of mine to be a singer,” Sajak told Teen Vogue at the time. “When I started playing guitar and performing more often, my passion for music became a top priority. With each new song I record and music video I release, I see my dreams becoming a reality.”
How the relationship went public
The courtship played out almost entirely in public, and with a certain marketing instinct. In December 2025, Olson posted what he called his official 2026 boyfriend application on Instagram, noting he had been single for more than five years.
Four months later, in April 2026, the couple confirmed the relationship with a photo taken at Disney, captioned simply: “Applications closed.” It was a tidy piece of personal branding, the kind of announcement cycle usually reserved for product launches.
In June, Olson expanded on the relationship in an Instagram tribute.
“I've never met someone I thought I could spend every day with until I met her,” Olson wrote. “And a major reason why is because we can be our true selves around each other. If you think you haven't found ‘the one' yet and that it's ‘too late,' trust me, it's not. Sometimes life only gives you what you truly want when you've been patient enough. So the moral of the story? Don't rush it, and never settle.”
Sajak has been equally public in her support. After Olson's week one performance on Dancing With the Stars in September, she wrote on social media: “Seeing @jacksonolson_ chase his dreams and shine in the ballroom is the joy of a lifetime. Keep watching, keep voting...he's just getting started!!!!!”
Olson's run on Dancing With the Stars
Olson is paired with professional dancer Emma Slater on season 35 of the ABC competition. ABC's profile of Olson describes him as a standout second baseman for the Savannah Bananas and a prolific content creator whose social channels cover baseball, family, relationships, and coming of age.
In an interview with Elite Daily, Olson said he largely avoids reading online commentary on his routines. He described his post-show routine as ordering food immediately and relaxing, adding that he is lucky to spend that time with Sajak rather than cooling down in a busy airport as he did during his baseball years.
During week four of the competition, Olson celebrated his 29th birthday on October 6. Sajak marked the occasion with an Instagram tribute: “Happy birthday to the absolute ray of sunshine that is @jacksonolson_. Forever thankful to be in your orbit.”
Family ties remain central
Sajak's social media shows a close relationship with her father and her mother, Lesly Brown. In a September video, she described herself as the opposite of a child who grows up and never needs their parents, captioning the post: “This 31-year-old will always be their little girl.”
She has also posted Father's Day tributes, including a compilation of videos of her and her father watching baseball games. “Behind every girl who loves baseball is a dad who taught her how,” she wrote. “Some things never change. Happy Father's Day!”
People magazine has also profiled Olson's parents, Dan and Laura Olson, as interest in the ballplayer's background grows alongside his television exposure.
Why the story travels
For anyone tracking the economics of modern celebrity, the Olson-Sajak pairing is a compact case study. A baseball content creator with a self-deprecating public persona meets a lawyer turned television correspondent from an entertainment dynasty, and the result is a cross-platform engagement engine spanning Instagram, ABC primetime, and a 44-year-old game show franchise.
Wheel of Fortune, now distributed by Sony Pictures Television, continues to demonstrate the enduring value of legacy formats when paired with digital-first content strategies. Sajak's correspondent role, created in 2021, is part of that modernization push: the show meets younger audiences where they already are.
Olson, for his part, keeps competing. Season 35 of Dancing With the Stars airs weekly on ABC, with Sajak, by her own account, among the loudest votes in his corner.
FAQ
Who is Jackson Olson's girlfriend?
Jackson Olson's girlfriend is Maggie Sajak, 31, a licensed California attorney and the social media correspondent for Wheel of Fortune. They went public with their relationship in April 2026.
Is Maggie Sajak related to Pat Sajak?
Yes. Maggie Sajak is the daughter of Pat Sajak, who hosted Wheel of Fortune from 1981 until his retirement, and of Lesly Brown.
What does Maggie Sajak do for a living?
She works as the social media correspondent for Wheel of Fortune, a role she took on in 2021. She is also a licensed attorney in California and previously pursued a country music career at 16.
When did Jackson Olson and Maggie Sajak go public?
In April 2026, the couple shared an Instagram photo taken at Disney captioned “Applications closed,” confirming their relationship.