Jackson Olson hit a home run when he started dating Maggie Sajak. The Savannah Bananas player made an emotional post about his girlfriend, who he claims is “the one.”
Olson, who will compete on Season 35 of Dancing With the Stars, shared a photo on his Instagram on June 19. In the photo, he and Sajak are at Disney World in Orlando, standing in front of the Epcot ball.
He wore a King Triton/The Little Mermaid jersey-style shirt with a hat that said “Sixteen.” Sajak donned an orange dress, Mickey ears that were Toy Story-themed, and a Mickey Mouse Lululemon bag. She also had a grape soda pin attached to her dress, which is a reference to the movie Up.
The baseball player apologized for “getting emotional” in the caption, which he said he rarely does on social media. “As you know, my posts aren’t typically sentimental… and they NEVER make you guys cry or feel any emotions. And this one is no different… I promise,” Olson wrote.
“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. To like me for me and not for what I post on social media. To love their family and enjoy spending time with them. To not take life so seriously and not care what other people think. 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,” he admitted.
“If you think you haven’t found ‘the one’ yet and that it’s ‘too late,’ trust me, it’s not. Sometimes life only gives you what you truly want when you’ve been patient enough. So the moral of the story? Don’t rush it, and never settle. (And yeah… loving Disney was an added bonus for us both.”
Sajak replied to his post, saying, “Beyond thankful. For patience. For love. For you (btw everyone please imagine how much I AM CRYING).”
Olson and the Wheel of Fortune social correspondent hard-launched their relationship in April. The joint announcement was a photo of them in front of Cinderella’s castle in Disney World. The caption read, “Applications closed.”
It is not clear how the two met or how long they have been dating, but it seems as though Olson is in it for the long haul.
Sajak previously dated 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.
Olson had kept his past relationships private and admitted that he had been single for five years prior to dating Sajak. In December 2025, he made a “Boyfriend Application” video, explaining why he would be great in a relationship.
@jacksonolson_ Not sure if this will help me or hurt me 😭 #single #dating ♬ original sound – thesavbananas
Since publicizing their relationship, the couple has posted about each other consistently. Most of the photos have been of them in Disney World.
There is no doubt, Sajak will be in the audience when her boyfriend competes on DWTS this fall. She may also attend some Savannah Banana games as the team travels across the USA.
Maybe Olson will appear on a future season of Celebrity Wheel of Fortune. Who knows?
Wheel of Fortune, Streaming on Hulu & Peacock, Season 44 Premieres September 2026