Who Is ‘DWTS’ Season 35 Cast Member Jackson Olson Dating? Here’s Why Maggie Sajak’s Name Might Sound Familiar

Who would you think is on Dancing With the Stars: The daughter of retired Wheel of Fortune host Pat Sajak, who still appears on the show herself, or the player for the Savannah Bananas, an exhibition baseball team that combines the sport with silly hijinks? They both sound very appropriate for the dance competition show, but this time around, the competitor is baseball player Jackson Olson. Maybe he’s not quite as well known as fellow cast members like Jenna Dewan and Julia Stiles, but hey, he’s got over 2 million followers on TikTok. That’s pretty impressive for a Banana Ball player!And when Jackson hits the dance floor starting Tuesday, September 15, he’ll surely be cheered on by his game show royalty girlfriend, Maggie Sajak. (Maybe her time will come next season?) Jackson and Maggie made their relationship public earlier this year, and since then they’ve continued to share moments from their time together on social media. Keep reading to learn more about Maggie, her career, and her relationship with Jackson.She works for Wheel of Fortune. After over 40 years as host, Pat Sajak retired from Wheel of Fortune in 2024. But while her dad is no longer on the show, Maggie is still part of the team. She is the social media correspondent for the game show, a position she’s held since 2021, according to her bio on the Wheel of Fortune site. In this role, the 31-year-old appears on the show’s social media pages, but she also pops up on the actual episodes. In addition, she’s filled in for Vanna White as co-host before.She went to law school.Maggie Sajak could pivot from gameshow social correspondent to lawyer, if she ever wanted to. (And would maybe become the only person to ever make that particular career move.) After attending undergraduate college at Princeton, she completed a postgrad program at Columbia, and then graduated from Georgetown Law.She had a teenage foray into country music.When she was a teenager, Maggie released a few country singles, including songs called “First Kiss” and “Wild Boy.”In a 2013 interview with Billboard, she said that she wanted to be a singer from when she was a little kid, and when she got a bit older and was given a guitar, her interest only grew. “I would spend hours a day after school, going back to my room and playing guitar. It was always an escape for me, and turned into a passion,” she said.She and Jackson went Instagram official in April.In April, Maggie and Jackson confirmed their relationship by sharing a joint post to Instagram of them posing together and captioned it, “Applications closed.” As People reports, this is a reference to Jackson previously saying that he was looking for love in a social media video and giving his “2026 boyfriend application.”In the video, he shares a bunch of facts about himself, including that he loves musicals and dances on a baseball field for a living. He also includes, “We’re not going to Europe on vacation, we’re going to Disney.”Maggie seems just fine with this last part! Their “applications closed” post is taken at Disneyland and they’ve shared posts of other Disney trips since, including to the Disney resort in Hawaii. Disney is the company behind DWTS, so this works out very well for everyone involved. You know he’s already manifesting making it to Disney Night.