Jackson Olson is heading into Season 35 of Dancing with the Stars as the first Savannah Banana to take the ballroom floor. The casting note gives ABC a fresh crossover story, but the larger draw is Olson’s public relationship with Maggie Sajak.
Olson and Sajak have been dating since October 2025, and he has already said he had “kind of given up on finding a girl I wanted to be with” before meeting her. He added that he wanted someone with “the same morals” and “a kind soul,” then said he found “all of that and more with Maggie.”
Olson and Maggie Sajak
That relationship is now part of the publicity around his DWTS run. Sajak is the social media correspondent for The Price Is Right and the daughter of Pat Sajak, which puts Olson’s ballroom turn in a very public lane before Season 35 even gets rolling.
Olson also said, “I’ve never met someone I thought I could spend every day with until I met her. And a major reason why is because we can be our true selves around each other.” For a contestant whose profile is built on performance, that line does more than sell a romance: it explains why this pairing has become part of the story attached to his new television role.
Dodgers game to Disney World
The couple met online after attending the same Dodgers game, which complicates the simpler version that they just met there. That timeline matters because it shows the relationship began with a shared public event, then moved into a private connection online before the Disney World photos turned it into a visible couple story.
On April 21, 2026, Olson posted his first picture with Sajak in front of Cinderella’s Castle in Disney World, and he wrote, “Applications closed.” In that photo, she wore Savannah Bananas yellow, a small detail that tied the relationship back to his team identity without needing any extra explanation.
June vineyard trip
In June, Sajak posted photos from a vineyard trip and wrote, “A duck, a llama and a banana walk into a vineyard.” Before Olson started training for DWTS, the couple also took a flight to Hawaii, and Sajak asked, “Is Hawaii to Manhattan considered island hopping?”
Jackson Olson’s Season 35 run now has a clear off-camera storyline attached to it: a first-time DWTS appearance for a Savannah Banana, and a relationship that has already moved from a Dodgers game to online messages to Disney World. The open question is how the show will handle that added attention once the ballroom floor becomes the main stage.
