Savannah Bananas' Jackson Olson Confirms He's Dating Pat Sajak's Daughter Maggie Sajak
Jackson Olson has revealed that he’s officially off the dating market and he’s now in a relationship!
The 28-year-old baseball player and entertainer, who plays for the Savannah Bananas, just hard-launched his new relationship with Maggie Sajak.
For those who don’t know, Maggie is the daughter of former Wheel of Fortune host Pat Sajak and she has served as a correspondent for the show over the years.
Jackson took to Instagram on Tuesday (April 21) to share a photo of him and Maggie standing in front of the castle at a Disney park following a recent visit.
“Applications closed✅,” he captioned the photo.
Keep reading to find out more…
Back in December 2025, Jackson made a viral TikTok that noted he was accepting applications to be his girlfriend.
“As some of you know, I’ve been single for over 5 years. So here is my official 2026 boyfriend application,” he captioned the video, in which he promised a trip to Disneyland for his next girlfriend.
It looks like he stayed true to his word!
Jackson is the most popular player on the Savannah Bananas, an exhibition team playing a variation of baseball known as Banana Ball. The team is known for their TikTok performance videos.
@jacksonolson_ Not sure if this will help me or hurt me ???? #single #dating ♬ original sound – thesavbananas