jackson olson and Maggie Sajak have made their relationship public after sharing a Disney castle photo on April 21 in Eastern Time. The post showed the pair together with a simple message, “Applications closed, ” ending weeks of curiosity around the connection. The reveal comes after Olson’s earlier “2026 boyfriend application” video drew attention online and framed the relationship as one many followers had already been watching closely.
Jackson Olson Romance Moves Into the Spotlight
Maggie Sajak, 31, the daughter of longtime Wheel of Fortune host Pat Sajak, shared the image with Olson, an infielder for the Savannah Bananas. Olson, 28, posted the same photo, making the reveal a coordinated public moment rather than a quiet soft launch. The setting, in front of a Disney castle, matched the playful tone that surrounded Olson’s earlier approach to dating and gave the announcement an instantly recognizable visual hook.
The relationship follows Olson’s viral TikTok in December, when he described himself as being single for more than five years and opened what he called his official 2026 boyfriend application. In that video, he highlighted that he is a baseball player who also dances on the field, loves Disney, knows “more Taylor Swift songs than you, ” and enjoys musical theater. That earlier video created the frame for this moment, and the new post now suggests the process has reached a clear end.
How the Announcement Landed
Fans responded quickly in the comments, turning the announcement into a celebration. Some focused on the surprise of seeing Pat Sajak’s daughter in the spotlight, while others leaned into the wordplay around Olson’s baseball career and the “puzzle” theme tied to the Sajak family name. On the same day, Olson also shared a clip from Elf in his Instagram Stories, pairing it with the line, “I’m in love and I don’t care who knows it, ” and added, “Me right now. ”
The post also marks a notable personal moment for Maggie Sajak. The romance is her first public relationship since her split from Scottish actor Ross McCall. It also places her more visibly in the public eye at a time when she already holds a role with Wheel of Fortune as the show’s social correspondent.
Jackson Olson, Pat Sajak, and the Family Context
Maggie is part of a family long associated with Wheel of Fortune, alongside her brother Patrick, 35. Her public profile has grown through her work connected to the show, and the new relationship adds another layer to that visibility. Pat Sajak’s name remains central to the response, but the focus of this announcement is the couple’s choice to make the relationship public in a clear and uncomplicated way.
For now, the message appears settled: the “application” is closed, and jackson olson and Maggie Sajak have stepped into the public conversation as a couple. What happens next will likely play out in the same public, social-first way that brought the relationship into view in the first place.
