Who Is Jackson Olson Dating? The Savannah Bananas Star Went Instagram Official
"Applications closed."
Published May 13 2026, 10:13 a.m. ET
Jackson Olson recently sparked major online buzz after revealing he is officially off the market. The Savannah Bananas player and social media personality shared a relationship update that quickly caught fans’ attention.
The baseball star hard launched his romance in April 2026 with a Disney-themed Instagram post captioned, “Applications closed.” The upload referenced Olson’s viral “girlfriend application” video posted on TikTok and Instagram from earlier this year, when he joked about searching for a partner after being single for more than five years.
Jackson Olson’s girlfriend recently appeared in his Instagram post.
Jackson confirmed his relationship with Maggie Sajak in a joint Instagram post shared on April 21, 2026. The pair posed together in front of Cinderella Castle at Disney World’s Magic Kingdom in Florida.
Maggie is the daughter of longtime Wheel of Fortune host Pat Sajak and currently works as the show’s social correspondent. In the photo, she wore Minnie Mouse ears while placing her hand on Jackson's chest as he wrapped an arm around her.
Several Savannah Bananas players reacted to the relationship reveal in the comments section. Teammate JT Sokolove joked, “Breaking news. He has found his other side!” while teammate Kyle “KJ” Jackson celebrated the post with clapping emojis.
Jackson Olson plays for the Savannah Bananas.
Jackson is best known as a second baseman for the Savannah Bananas, the viral exhibition baseball team famous for combining comedy, dancing, and entertainment with the sport. The team has built a massive online following for its fast-paced style of play.
Beyond baseball, Jackson gained popularity through TikTok and Instagram videos focused on relationships, family life, food, and behind-the-scenes moments with the Bananas. His upbeat personality and dancing clips helped him become one of the team’s most recognizable stars.
The Savannah Bananas have become a massive social media sensation in recent years because of their comedic and fast-paced approach to baseball. The team is often compared to the Harlem Globetrotters thanks to its mix of athletic performances, dancing routines, and fan-focused entertainment.
Jackson Olson is joining ‘Dancing With the Stars.’
Jackson’s growing popularity recently earned him a spot on Season 35 of Dancing With the Stars. ABC announced in May 2026 that the Savannah Bananas player would compete on the upcoming season alongside reality TV personalities Maura Higgins from The Traitors and Love Island and Ciara Miller from Summer House.
According to Good Morning America, the full celebrity cast and professional dancer lineup will officially be revealed Sept. 2. The competition series is expected to air live this fall on ABC and Disney Plus, with episodes streaming the next day on Hulu.