Pat Sajak's Daughter Maggie and Savannah Bananas' Jackson Olson Go on Sweet Disney Date: ‘No More Single Rider’
Pat Sajak's Daughter Maggie and Savannah Bananas' Jackson Olson Go on Sweet Disney Date: ‘No More Single Rider’
Natalia SenanayakeThu, June 18, 2026 at 6:42 PM UTC
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Maggie Sajak and Jackson Olson at Disney WorldCredit: Jackson Olson/Instagram -
Maggie Sajak and Jackson Olson shared highlights from their Disney World date in a playful Instagram Reel
The couple enjoyed rides, snacks, and a romantic dinner at Disney's Be Our Guest Restaurant
Olson previously joked about wanting a girlfriend to visit Disney with before hard-launching their relationship in April
Maggie Sajak and Jackson Olson are sharing a look inside their magical date at Disney World together!
The 28-year-old Savannah Bananas second baseman and influencer — who will also be joining season 35 of Dancing with the Stars — revealed a glimpse of his sweet outing at the Most Magical Place on Earth with his girlfriend, 31, in a joint Instagram Reel on Wednesday, June 17.
Olson begins the video by walking through the park and playfully mouthing along to the words: "I wish I had a girlfriend to go to Disney with, that would be so fun."
The scene then cuts to Sajak, who is the daughter of former Wheel of Fortune host Pat Sajak, as she responds, "Yeah, I wish I had a boyfriend to go with, how cool would that be."
Credit: Jackson Olson/Instagram
After the two stop short and look at each other with a confused expression on their faces, they then point at each other and smile before reaching their arms out to hold hands.
From there, a number of clips featuring the couple enjoying activities around the Florida theme park together are shown. After posing for a sweet selfie at the Magic Kingdom landmark Cinderella Castle, the two then ride a roller coaster together and cool off with a fun drink.
They also showed some of the snacks they tried in between rides, as well as the cute dinner date they had at the park's Be Our Guest Restaurant.
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"No more single rider 🥹," Olson wrote in the caption as Taylor Swift's "Opalite" played in the background.
In April, Olson and Maggie shocked fans when they hard-launched their relationship with another Disney-themed Instagram post that showed the new couple cozying up together in front of Cinderella Castle. "Applications closed✅," Olson captioned the post.
The sweet snap showed Maggie rocking a pair of Minnie Mouse ears as she placed her hand on her boyfriend's chest, while he wrapped his arm around her.
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News of the couple's romance came four months after Olson revealed he was looking for a girlfriend in a post shared to TikTok and Instagram.
In the video, Olson explained that he had been single for over five years and was "getting pretty tired of it recently," as he mouthed along to One Direction's "Kiss You." He added, "So here is my official 2026 boyfriend application."
He continued that he wanted to take his future girlfriend to Disney and that his parents were "sick" of him not having a partner. He also noted that he "dances on baseball fields for a living," is a big Taylor Swift fan, has an "unhealthy obsession with musicals," has the "diet of a 12-year-old," and is "very unphotogenic."
on People
Source: “AOL Entertainment”
