Maggie Sajak made her romance with Jackson Olson public on Tuesday, April 21, posting a Disneyland photo on Instagram that left little room for doubt. The 31-year-old Wheel of Fortune social correspondent shared the image with the 28-year-old Savannah Bananas star, and he answered with a caption that read, “Applications closed ✅.”
The photo showed Sajak in sparkly Minnie Mouse ears, a white tee and a black skirt. Olson was dressed for the trip in a backwards hat, sunglasses, a Chicago tee and gym shorts, turning a theme-park snapshot into a relationship reveal.
The post carried extra weight because Olson had already turned the romance into a bit months earlier. In December 2025, he announced an official 2026 boyfriend application on TikTok, saying, “As some of you know, I’ve been single for over 5 years. So here is my official 2026 boyfriend application,” and saying the application included a promised Disneyland trip.
For Sajak, the reveal marks her first public relationship since her split from Scottish actor Ross McCall. It also places her in the spotlight beyond the family name she has carried on the show for years. She is Pat Sajak’s daughter with Lesly Brown, who married on New Year’s Eve 1989, and she has built her own presence at Wheel of Fortune as the show’s social correspondent.
That visibility has grown over time. Sajak filled in during Pat Sajak’s 2019 health scare, when he needed surgery for a blocked intestine, and later took over Vanna White’s role in 2023 while White competed on Jeopardy! The newest post shows her stepping into a more personal kind of public attention, one that fans of the long-running game show will read as the first clear confirmation of a relationship that had already been teased online.
The question now is not whether the pairing is real; the Instagram post answered that. What matters next is how much of the couple’s life they choose to put in public, because Sajak’s role on Wheel of Fortune and Olson’s profile with the Savannah Bananas make this the sort of relationship that tends to travel fast once it is out in the open.
