COUPLESWho Is Jackson Olson's Girlfriend? All About Maggie Sajak

'Dancing With the Stars' Season 35 contestant Jackson Olson went Instagram official with his girlfriend, Maggie Sajak, in April.
Sept. 14 2026, Published 5:00 a.m. ET
Jackson Olson is officially off the market.
The Dancing With the Stars Season 35 cast member is dating Pat Sajak's daughter, Maggie Sajak, and the couple has been maintaining a long-distance relationship for months. In a May 1 interview with Us Weekly, Jackson opened up about his experience meeting his girlfriend's father, calling the retired Wheel of Fortune host "a great guy."
"Everybody's nervous to meet the father of the person they're dating, or mother or both," he said.
Jackson continued, "I'm a very weird person, I'm a very out there person. I'm not going to hold back who I am as a person, and people seem to enjoy that company. I'm happy that I'm able to be myself truly in every aspect now."
As their romance blossoms, scroll down to learn more about Jackson's girlfriend, Maggie.
Maggie Sajak Is Pat Sajak's Daughter

Jackson Olson is dating Pat Sajak's daughter, Maggie.
Maggie was born to Pat and his second wife, Lesly Brown, on January 5, 1995.
She made her debut on Wheel of Fortune when she was just one year old. More than two decades later, she temporarily stepped into Vanna White's role while White filled in as host for Pat, who was recovering from surgery at the time.
Maggie officially joined the show as its social correspondent in 2021.
"The Wheel of Fortune staff and crew have always been like an extended family," she said on her page on the game show's official website. "And I'm thrilled to be working with them. It's a real privilege to be able to treat the show's longtime viewers to a look at what goes on when the cameras aren't rolling."
Maggie Sajak Attended Law School

Maggie Sajak is one of Pat Sajak's two children.
When she's not in front of the camera, Maggie pursues interests outside of television.
Following her graduation from Princeton University, she completed a postgraduate program at Columbia University before earning her law degree from Georgetown University Law Center in 2023.
"Let the lawyer jokes begin…⚖️," she captioned a May 2023 Instagram update.
Maggie Sajak Is a Country Singer
Want OK! each day? Sign up here!

Maggie Sajak said she had always wanted to be a singer.
In addition to her TV gigs, Maggie also pursued a career in country music from a young age.
She recorded her debut single, "First Kiss," when she was 16 and went on to release additional songs, including "Wild Boy" and "If I Was Gonna Go."
"I knew when I was little, and someone would ask me what I wanted to be when I grew up, I would say a singer," Maggie told Billboard in 2013. "I also did dance classes when I was little, and got a little guitar when I was eight, and started playing around with it. Then, when I was 13, I got my Taylor guitar, which I still play now. Since then, I really knew this was what I really wanted to pursue as a career, because 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."
Jackson Olson and Maggie Sajak Went Instagram Official in April

Jackson Olson joined the cast of 'Dancing With the Stars' Season 35.
Jackson and Maggie made their Instagram debut in a joint post in April.
The baseball player wrote in the caption, "Applications closed✅."
In the May interview with Us Weekly, Jackson said he and Maggie have very different schedules and are navigating a long-distance relationship.
"It's really cool because we're obviously living very different lives right now on the opposite side of the country, but we're able to come together and just have an awesome relationship," he told the outlet. "I feel like in any relationship, you're trying to figure out how to see each other as frequently as possible, which is never something that I thought in my past I was going to want to do … but now I really do."
Despite being in the early stages of their relationship, Jackson revealed he wants to be intentional about making time for his girlfriend.
He continued, "It's just about planning and making sure you're setting aside time to see each other and make really cool experiences happen because a start of a relationship never happens again. You only get one chance at a start of a relationship."
Jackson Olson and Maggie Sajak Revealed They Met in 2025

Jackson Olson and Maggie Sajak opened up about their first meeting amid speculation.
A few months after confirming their romance, Jackson and Maggie shared the story of their first meeting in an Instagram video uploaded on September 6.
A lot of you guys have been asking how Maggie and I met," said Jackson. "No, it was not at Disney, believe it or not."
"On October 16 of last year, we both went to a Dodgers playoff game," he explained, adding they had followed each other on social media a month before the game.
Maggie also unexpectedly appeared in the background of one of his posts from the event.
"Then someone DM'd someone. Doesn't matter who, and the other person DM'ed back. We waved at each other," Maggie shared, while Jackson revealed she agreed to have a drink with him before the two returned to their respective seats.
Jackson concluded, "But as they say, the rest is history, and as you may know, I'm a lifelong Yankees fan, but the Dodgers will always have a special place in my heart."


