Inside ‘Wheel of Fortune’s Maggie Sajak & ‘DWTS’s Jackson Olson’s Relationship
We’re going bananas for this TV crossover couple!
2026 has been a massive year for Wheel of Fortune‘s Maggie Sajak and Dancing with the Stars celeb Jackson Olson, of Savannah Bananas fame. On April 21, Pat Sajak‘s daughter and the social correspondent for the beloved game show hard-launched her relationship with the dancer in an Instagram post. The couple posted an adorable photo that featured them posing in front of the Cinderella Castle at Walt Disney World in Orlando, Florida. “Applications closed,” they captioned their joint announcement. If that wasn’t enough, Olson was announced as a Dancing with the Stars contestant with pro Emma Slater soon after.
Below, Swooon has all the key details you need to know about Maggie Sajak and Jackson Olson’s relationship so far.
Who is Maggie Sajak dating?
Maggie Sajak is currently dating Jackson Olson. The 28-year-old hails from Connecticut, and he’s amassed quite the social media following. (More on his job below.) He has over one million followers on Instagram and two million on TikTok.
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In addition to the hard launch, Olson shared a clip of Will Ferrell‘s Elf character saying, “I’m in love. I’m in love. And I don’t care who knows it.” He wrote over the top, “Me right now.”
@jacksonolson_ Not sure if this will help me or hurt me 😭 #single #dating ♬ original sound – thesavbananas
In December 2025, Olson admitted that he’d been single for over five years, so he decided to reveal his “2026 boyfriend application” to the world. “Not sure if this will help or hurt me,” he captioned the video. This time around, it certainly helped! Olson took a big swing, and it paid off!
How did Jackson Olson and Maggie Sajak meet?
During a recent video, Olson and Sajak followed each other on social media before they met in person. During a Dodgers game, the two realized that they were at the same event, and Olson slid into Sajak’s DMs. The rest, as they say, was history.
What does Jackson Olson do for a living?
Olson is an infielder for the Savannah Bananas, an exhibition barnstorming baseball team based in Savannah, Georgia. This isn’t your traditional Major League Baseball team. The Savannah Bananas specialize in Banana Ball, which is all about putting fans first. The team tours all across the country.
Olson has been a part of the Savannah Bananas since 2022. He also played college baseball at the University of Hartford and Stetson University.
Who has Maggie Sajak dated in the past?
Sajak, 31, was previously linked to actor Ross McCall, who is 19 years her senior. They were spotted out together in March 2024 and kept their relationship very low-key. In September 2024, McCall briefly discussed his relationship but didn’t mention Sajak by name. “It’s early,” he said on Jenny Mollen‘s All the Fails podcast.
Dancing with the Stars, Season 35, Premieres Tuesday, September 15 at 8/7c, ABC
