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Maggie Sajak / Instagram
Jackson Olson is entering a new era as the first Savannah Banana to take the ballroom floor on Season 35 of Dancing with the Stars, which means Maggie Sajak is officially a DWTS WAG.
The Savannah Bananas star has been dating Sajak, the social media correspondent for The Price Is Right and daughter of former host Pat Sajak, since October 2025. They met online after attending the same Dodgers game.
Reflecting on Instagram, Jackson shared, “Last year I had kind of given up on finding a girl I wanted to be with. I remember thinking to myself that if I’m gonna date someone I want them to have the same morals I have and to have a kind soul… And somehow I found all of that and more with Maggie. 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.”
Ahead of the Season 35 premiere of Dancing with the Stars, we’re looking back at the certified Disney Adult couple’s relationship through their cutest pictures together.
Dancing With the Stars, Season 35, Tuesdays, 8/7c, ABC
Jackson Olson / Instagram
The hard-launch
On April 21, 2026, Olson posted his first picture with Sajak. In the photo, they posed in front of Cinderella’s Castle in Disney World. Letting the world know that the role of Jackson Olson’s girlfriend was officially filled, Jackson wrote, “Applications closed.”
Jackson Olson / Instagram
Savannah Bananas game
For this adorable pic, Sajak donned Savannah Bananas yellow to support her favorite player.
Maggie Sajak / Instagram
Vineyard trip
Sajak posted a collection of photos from their June trip to a vineyard, writing, “A duck, a llama and a banana walk into a vineyard.”
Maggie Sajak / Instagram
Date night noir
This black-and-white photo proves that Jackson Olson is truly the golden retriever boyfriend of everyone’s dreams.
Maggie Sajak / Instagram
All smiles in Disneyland
Olson and Sajak headed to the West Coast to say hi to their favorite mouse.
Jackson Olson / Instagram
Disney Part 3
This duo is not beating the Disney Adult allegations — and they don’t want to!
Maggie Sajak / Instagram
Hawaii adventure
Before Olson started training for DWTS, the couple took a flight to Hawaii. Sajak asked, “Is Hawaii to Manhattan considered island hopping?”
Maggie Sajak / Instagram
Hawaiian date night
Another sweet pic from the couple’s trip to Hawaii!
Maggie Sajak / Instagram
Duck lips
Who couldn’t love these two?!