Jackson Olson and Maggie Sajak Shut Down Speculation About How They Started Dating
Jackson Olson and Maggie Sajak are setting the record straight about the surprising way their relationship began.
The couple, who first made their romance public earlier this year, recently revealed that their love story did not begin at Disney World — despite the fact that their first major public relationship moment happened at the magical destination.
Instead, the pair traced their first real interaction back to a Dodgers playoff game in October 2025.
Olson, 28, and Sajak, 31, opened up about their relationship timeline in an Instagram video shared Sunday, September 6. The Savannah Bananas star explained that fans had been asking how he and Sajak first met, prompting the couple to finally reveal the details.
Their Love Story Started at a Dodgers Game
“ A lot of you guys have been asking how Maggie and I met,” Olson explained in the video.
The baseball player quickly cleared up one popular assumption.
“No, it was not at Disney, believe it or not,” he joked.
That clarification is understandable considering the couple’s relationship was first widely noticed after they shared photos together at Disney’s Magic Kingdom in Florida.
But their actual story began months earlier.
According to Olson, both he and Sajak attended a Dodgers playoff game on October 16, 2025.
The pair had already been following each other on social media for about a month, but they had apparently never properly connected in person before that night.
Sajak explained that both of them posted Instagram Stories showing they were at the game.
Then, almost by accident, she ended up appearing in the background of one of Olson’s posts.
That small social-media moment ultimately gave them a reason to interact.
One Instagram DM Changed Everything
Sajak explained that after seeing each other at the game, one of them eventually sent the other a direct message.
“Then someone DM’d someone. Doesn’t matter who, and the other person DM’d back,” she recalled.
The two eventually spotted each other at the stadium and waved.
Olson then asked Sajak if she wanted to grab a drink before they returned to their respective seats.
It was a relatively simple first meeting, but the connection clearly stuck.
“As they say, the rest is history,” Olson said.
He also couldn’t resist adding one more detail that made the story even more amusing.
Olson has been a lifelong Yankees fan, but after meeting Sajak at the Dodgers game, he admitted that the Dodgers will always have a special place in his heart.
Disney Was Their Public Relationship Debut
While Disney wasn’t where the couple initially met, it became an important location in their relationship story.
In April 2026, Sajak and Olson officially confirmed their romance on social media with a photo taken during a Disney trip.
Sajak cuddled up beside Olson in front of the Disney castle, instantly sending fans into a frenzy.
Olson later captioned the post, “Applications closed,” jokingly referencing his previous efforts to find a girlfriend online.
The announcement was particularly fitting because Olson had previously promised that his future girlfriend would get a Disney trip.
Just months earlier, the Savannah Bananas star had gone viral after posting a social-media “boyfriend application” while joking about being single for more than five years.
Olson Had Been Looking for Love Online
Before meeting Sajak, Olson was surprisingly open about his dating life.
In December 2025, he posted a TikTok explaining that he had been single for more than five years and was ready to find someone.
His humorous “2026 boyfriend application” quickly attracted attention online.
Among the things Olson highlighted about himself were his love of baseball, Taylor Swift, musicals and Disney.
He also joked about his quirks and promised that a future girlfriend would get a trip to Disneyland.
A few months later, that wish appeared to come true.
When Olson and Sajak went public with their relationship in April, the timing made the earlier dating post look almost prophetic.
Their Relationship Quickly Became a Fan Favorite
Since making their romance official, Olson and Sajak have shared glimpses of their relationship with fans.
One of the biggest moments came when Sajak attended one of Olson’s Savannah Bananas games.
Following the game, Olson shared a sweet photo of himself kissing Sajak on the forehead while she smiled beside him.
The couple also used Taylor Swift’s “Opalite” on their Instagram Stories, adding another pop-culture detail to their growing romance.
Their relationship has also been notable because of the distance between them.
Olson is based in Savannah, Georgia, while Sajak is based in Los Angeles.
That means their relationship requires plenty of planning, especially while Olson balances his baseball schedule and Sajak continues her work in entertainment.
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Jackson Olson Says the Distance Is Worth It
Despite living on opposite sides of the country, Olson has said that he and Sajak are committed to making the relationship work.
In an earlier interview with Us Weekly, Olson explained that the two live very different lives but are able to come together and enjoy their time together.
He described the relationship as something that requires planning and making sure they intentionally set aside time for one another.
For Olson, those efforts are worth it.
He also offered a particularly romantic perspective on the early stages of a relationship, saying that the beginning of a romance is something you only experience once.
That mindset seems to have shaped the couple’s approach as they navigate a long-distance relationship.
Olson Has Already Met Maggie’s Famous Dad
The relationship has also reached another important milestone: Olson has met Sajak’s father, longtime Wheel of Fortune host Pat Sajak.
In May, Olson confirmed that he had met the television icon and described him as a “great guy.”
Meeting the father of someone you’re dating can be intimidating, but Olson said he tried to remain completely himself.
He described himself as a very outgoing and unusual person and said he wasn’t interested in hiding his personality.
That attitude appears to have worked.
Olson said he was happy that he could be himself around the people in Sajak’s life.
Maggie Sajak Has Been Supporting Olson’s Baseball Career
Sajak has also embraced Olson’s unusual career with the Savannah Bananas.
The team has developed a huge online following for its energetic version of baseball, known as Banana Ball, which combines traditional baseball with entertainment, music, dancing and comedy.
Olson joined the Savannah Bananas in 2022 after gaining attention online as a baseball content creator.
He’s become one of the team’s most recognizable players and has built a major following through his social-media personality.
His relationship with Sajak has now added another layer to his public profile.
From Baseball Games to the DWTS Ballroom
Olson’s career is about to enter another major chapter.
The Savannah Bananas star is set to compete on season 35 of Dancing With the Stars, giving fans another chance to see him outside the baseball field.
Sajak has already publicly supported her boyfriend’s new challenge.
After Olson’s DWTS casting was announced, she celebrated him on Instagram Stories and expressed how proud she was of his opportunity.
The transition from Banana Ball to ballroom dancing could be a major challenge for Olson, but his background as an entertainer may give him an advantage.
His ability to perform for large crowds and create viral moments is already a major part of his Savannah Bananas persona.
Now he’ll have to translate that energy into choreography.
Olson Previously Called Maggie “The One”
The couple’s relationship has also become increasingly serious.
In June, Olson shared an emotional post about Sajak and suggested that he had found the person he had been waiting for.
He explained that he had previously felt like he might never meet someone who shared his values and allowed him to be completely himself.
Then he met Sajak.
Olson said he had never previously met someone he could imagine spending every day with.
He credited their ability to be their authentic selves around each other as one of the biggest reasons he felt so strongly about their relationship.
The Couple’s Origin Story Is More Ordinary — and More Romantic — Than Fans Thought
In the end, there was no elaborate Hollywood setup or perfectly planned Disney introduction.
Their relationship started with two people attending the same baseball game.
They happened to post about being there.
One appeared in the other’s Instagram Story.
Someone sent a DM.
They waved.
Then came a drink.
And eventually, the casual interaction turned into a relationship that has now captured plenty of attention online.
Their Disney debut may have looked like the beginning of their romance, but the couple’s latest explanation reveals that the real beginning happened months earlier at Dodger Stadium.
And perhaps that’s what makes their story even more fun.
What looked like a carefully planned celebrity romance actually started with something much simpler: two people unexpectedly realizing they were in the same place at the same time.
Now, with Olson preparing for Dancing With the Stars and Sajak continuing to support him from Los Angeles, their relationship is entering a very different chapter.
For a couple whose story began with a random Instagram Story at a baseball game, the next act could be just as entertaining.