COUPLESMaggie Sajak and Jackson Olson Finally Reveal How Their Romance Really Began

Maggie Sajak and Jackson Olson revealed how their romance really began.
Sept. 8 2026, Published 6:32 a.m. ET
Maggie Sajak and Jackson Olson are finally setting the record straight about how their relationship began.
The couple, who went Instagram official earlier this year with a romantic photo at Disney World, recently revealed that their first encounter actually happened months before that magical-looking debut.
“A lot of you guys have been asking how Maggie and I met,” Olson, 28, said in an Instagram video shared Sunday, September 6, alongside Sajak, 31.
“No, it was not at Disney, believe it or not,” the Savannah Bananas player joked.
Maggie Sajak and Jackson Olson opened up about their first date.
Maggie Sajak and Jackson Olson Recall Their Unexpected First Encounter

Maggie Sajak and Jackson Olson connected after an unexpected Instagram moment.
The pair's relationship became public in April when they shared a joint Instagram post showing them posing in front of Cinderella Castle at Magic Kingdom in Florida. Olson captioned the sweet photo, “Applications closed✅.”
But the real beginning of their love story was much more low-key.
“On October 16 of last year, we both went to a Dodgers playoff game,” he explained while sharing throwback footage from the early days of their relationship.
According to Sajak, the two had actually followed each other on social media about a month before the game. When they both posted Instagram Stories from the Dodgers game, fate seemingly gave them a little push.
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Maggie Sajak and Jackson Olson made their romance Instagram official in April.
The country music singer happened to appear in the background of one of Olson’s posts from that night.
“Then someone DM’d someone. Doesn’t matter who, and the other person DM’ed back. We waved at each other,” she recalled.
He added that Sajak agreed to grab a drink with him before the two returned to their respective seats.
“But as they say, the rest is history,” the athlete said, adding, “And as you may know, I’m a lifelong Yankees fan, but the Dodgers will always have a special place in my heart.”
The romance quickly became serious. Shortly after their Instagram debut, he shared a clip from Elf on his Instagram Story in which Will Ferrell’s character declares, “I’m in love and I don’t care who knows it.”
Maggie Sajak and Jackson Olson Are Making Long Distance Work

Jackson Olson got candid about meeting Maggie Sajak’s famous father, Pat Sajak.
Olson has also already met Sajak’s famous father, retired Wheel of Fortune host Pat Sajak.
“I have [met Pat], he’s a great guy,” the 28-year-old told Us Weekly in May.
“Everybody’s nervous to meet the father of the person they’re dating, or mother or both," he continued.
While the couple live on opposite sides of the country, with Maggie based in Los Angeles and Jackson in Savannah, Georgia, they say they are making the distance work.
“It’s really cool because we’re obviously living very different lives right now on the opposite side of the country, but we’re able to come together and just have an awesome relationship,” the baseball star shared.
“I feel like in any relationship, you’re trying to figure out how to see each other as frequently as possible. It’s just about planning and making sure you’re setting aside time to see each other and make really cool experiences happen because a start of a relationship never happens again. You only get one chance at a start of a relationship," he added.


