Jackson Olson is heading into Season 35 of Dancing with the Stars with a relationship that is already out in the open. The Savannah Bananas star has been dating Maggie Sajak since October 2025, and the pair’s first public photo together landed on April 21, 2026.
That timing is part of why the interest has grown now. Olson is entering the ballroom as the first Savannah Banana to take the floor on Season 35, and Sajak, a social media correspondent for The Price Is Right and the daughter of Pat Sajak, is suddenly part of the story around his debut. The April 21 photo showed them in front of Cinderella’s Castle in Disney World, with Olson writing, “Applications closed.” Sajak wore Savannah Bananas yellow, a small detail that made the post feel less like a reveal than a stamp of approval.
The relationship began the way a lot of modern ones do: online, after they had both attended the same Dodgers game. What is still not fully clear is who made the first move or how the contact started, but the result is no mystery. By October 2025, they were together, and Olson later said he had once given up on finding a girl he wanted to be with before realizing he had found that person in Sajak. That line matters because it turns the public photos into something more specific than a celebrity soft launch. It is a declaration of fit.
Sajak has kept feeding that picture in her own way. In June, she posted photos from a trip to a vineyard and wrote, “A duck, a llama and a banana walk into a vineyard.” Before Olson began training for DWTS, the couple also took a flight to Hawaii, where Sajak joked, “Is Hawaii to Manhattan considered island hopping?” The posts present them as a couple comfortable enough to be playful in public, and comfortable enough to build a shared identity around travel, jokes and bright yellow team gear.
What comes next is simple enough: Olson’s Season 35 run on Dancing with the Stars will draw the next wave of attention, and with it a wider audience for a relationship that has already moved from a Dodgers game to Disney World, Hawaii and a vineyard. The bigger unanswered detail is not whether they are together. It is how a one-night meeting turned into something both of them now seem willing to show in full view.
