Jackson Olson is heading into Season 35 of Dancing with the Stars with a relationship that is no longer tucked away online. The Savannah Bananas star is dating Maggie Sajak, and the couple’s first public photo together was posted on April 21, 2026, just as his ballroom run moved into view.
That timing matters because Olson is being billed as the first Savannah Banana to take the ballroom floor on Season 35 of Dancing with the Stars, a first for the team in the simplest sense: no one from the group had reached that stage before him. For readers searching his name now, the draw is not only the TV debut but the woman beside him in the photos. Sajak is the social media correspondent for The Price Is Right and the daughter of Pat Sajak, which makes the pairing easy to spot and harder to ignore.
Olson and Sajak have been dating since October 2025, after meeting online following attendance at the same Dodgers game. On April 21, Olson posted the first picture of them together, posing in front of Cinderella’s Castle in Disney World. He wrote, “Applications closed,” while Sajak wore Savannah Bananas yellow in the image, a small visual cue that made the relationship feel public without turning it into an announcement.
By June, Sajak had posted a collection of photos from a vineyard trip and offered the line, “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 she later asked, “Is Hawaii to Manhattan considered island hopping?” The pair’s social media trail has been playful, coordinated and unusually specific, with Disney World, Hawaii and the vineyard all serving as shorthand for a relationship that appears to have settled into its own rhythm.
There is, however, one detail that keeps the story from reading like a polished rollout. Olson and Sajak are said to have met online after attending the same Dodgers game, which leaves the connection open to interpretation even as the timeline is fixed. What is clear is that the dating began in October 2025 and became public only after Olson’s DWTS profile started rising, a sequence that links the romance to the television moment now bringing it fresh attention. His run on Season 35 is the next confirmed step, and with it, the couple’s quiet online beginning is likely to keep drawing notice.
