For Savannah Bananas third baseman Jackson Olson, life on and off the diamond is a whirlwind of bananas baseball, viral fame, and a high-profile romance that has fans buzzing. The 24-year-old social media sensation recently confirmed he's dating Maggie Sajak—daughter of legendary Wheel of Fortune host Pat Sajak—and he's not shying away from the spotlight.
Olson and Sajak went public two weeks ago with an adorable Disney World photo captioned “Applications closed,” signaling the official start of their relationship. Since then, the couple has been making headlines, and Olson is finally opening up about what it’s like to date the daughter of a TV icon.
In a candid interview, Olson admitted there were nerves before meeting Pat Sajak for the first time. “Everybody’s nervous to meet the father of the person they’re dating, or mother or both,” he told Us Weekly. But the meeting went smoothly—Olson described Pat as “a great guy” and emphasized that he didn’t try to be anyone else. “I’m a very weird person, I’m a very out there person. I’m not going to hold back who I am as a person, and people seem to enjoy that company. I’m happy that I’m able to be myself truly in every aspect now.”
That authenticity has clearly worked for Olson. With over 3.1 million followers across TikTok and Instagram, he’s built a massive fanbase by blending athletic talent with offbeat humor. On the field, he’s a standout for the Savannah Bananas—a team known for its viral, fan-first brand of baseball. Olson was a three-sport star at New Milford High School and posted a .464 batting average with 23 RBIs in his senior season.
Maggie Sajak, meanwhile, has followed in her father’s footsteps as the social media correspondent for Wheel of Fortune since 2021. While she’s used to the camera, her relationship with Olson has thrust her into a new kind of spotlight—one that includes red carpets, amusement parks, and plenty of playful social media posts.
The couple’s Disney World “hard launch” was a playful nod to their fun-loving dynamic, and fans ate it up. But Olson’s willingness to be vulnerable about meeting the Sajak family has also earned him respect. “I’m happy that I’m able to be myself truly in every aspect now,” he said, hinting that the relationship has brought him a new level of confidence.
For those wondering what’s next for the pair, Olson isn’t giving away too much—but he’s clearly enjoying the ride. Whether it’s on the diamond or at a theme park, the Bananas star is proving that staying true to yourself is the best game plan. Maggie Sajak Stuns Fans in Fiery Red Dress, Makes Relationship Official earlier this month, and the couple shows no signs of slowing down.
And as for the Savannah Bananas? They’ve got a surprise pop-up game hitting Texas High School tonight, keeping their brand of unpredictable fun alive. Olson’s love life might be making waves, but the Bananas’ rogue spirit is as strong as ever.
In a world where athletes often guard their personal lives, Olson’s openness is refreshing. He’s not just swinging for the fences—he’s doing it with a smile, a viral dance, and the daughter of a game show legend by his side. And honestly? That’s a home run in anyone’s book.
