Maggie Sajak Debunks Rumor About How She Met Boyfriend Jackson Olson

Their love of Disney made their relationship grow stronger, but Maggie Sajak and baseball player Jackson Olson did not meet at the most magical place on Earth. The couple shared the story of how they met and how they were in the right place at the right time.

“Hey guys. A lot of you have been asking how Maggie and I met,” Olson said in an Instagram post with Sajak hanging on his neck. “No, it was not at Disney,” he  revealed.

“Believe it or not,” Sajak said.

“But today we’re going to tell you how we met,” Olson said.

The couple said that they both went to a Los Angeles Dodgers playoff game on October 16, 2025. They had both shared photos from the game to their Instagram Stories. Olson shared that they had followed each other and liked each other’s posts, but hadn’t talked yet.

Sajak and Olson were in very close proximity at the stadium. Sajak DM’d Olson saying, “You’re here?!” He told her to meet him for a drink if she wanted to.

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A post shared by Jackson Olson (@jacksonolson_)

They waved at each other, got a drink, and then went back to their own seats. “Because I was really, really nervous,” Olson admitted. “As they say, the rest is history.”

“As you may know, I’m a lifelong Yankees fan, but the Dodgers will always have a special place in my heart,” the Savannah Bananas player said. The couple shared that they were posting this story from their Disney hotel room.

Olson will compete on Season 35 of Dancing with the Stars, so Sajak is bound to be in the audience. Since Sajak is the social correspondent for Wheel of Fortune, Olson may show up to some tapings when he has the chance.

The next day, the couple shared photos of them in Disneyland. “Nothing can stop us from a @disneyland trip! Not even a rainy day,” Sajak captioned the post.

“We would go in a hurricane,” Olson replied.

The couple went public with their relationship on April 21 in a joint Instagram post. “Applications closed,” the post was captioned.

On June 23, Olson said that he “found the one” with Sajak.