Maggie Sajak and Jackson Olson‘s love story reads like a rom-com script — a chance meeting at a Los Angeles Dodgers playoff game, a hard launch at Disney’s Cinderella Castle and beyond.
The Wheel of Fortune social correspondent, the daughter of former host Pat Sajak, confirmed her romance with the Savannah Bananas star in April 2026.
“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,” Olson exclusively told Us the next month of their long-distance romance. “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.”
Scroll below for Maggie and Olson’s complete relationship timeline:
October 2024
Maggie and Olson first crossed paths on October 16, 2024, at a Los Angeles Dodgers playoff game. The pair had followed each other on social media one month prior, soon noticing that they were each at the game. Maggie subsequently realized that she happened to appear in the background of one of Olson’s snapshots.
“Then someone DM’d someone — doesn’t matter who — and the other person DM’ed back,” Maggie recalled in a September 2026 social media video. “We waved at each other.”
Olson added, “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.”
April 2026
Six months after their Dodgers meet-cute, the pair took their relationship public.
“Applications closed ✅,” Olson wrote via Instagram, sharing a photo of the couple in front of Disney’s Cinderella Castle at Magic Kingdom in Florida.
Shortly after, the baseball player shared a clip from the movie Elf on his Instagram Stories, in which Will Ferrell’s character declares, “I’m in love and I don’t care who knows it.”
May 2026
By early May, Olson had reached a milestone that many new boyfriends dread: meeting their partner’s father. And when the dad in question happens to be a beloved game show host, the pressure can only escalate.
“I have [met Pat]. He’s a great guy,” Olson exclusively told Us. “Everybody’s nervous to meet the father of the person they’re dating, or mother or both.”
Being himself, he said, has paid off with the Sajak family.
“I’m a very weird person, I’m a very out-there person,” Olson said. “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.”
Later that month, Maggie turned out to support Olson at one of his Savannah Bananas games at Atlanta’s Truist Park. Olson posted a photo kissing Maggie on the cheek with the caption, “Bananas win… and so did we 😊.”
September 2026
Olson joined the cast of Dancing With the Stars season 35, pairing up with pro partner Emma Slater. Throughout his ballroom journey, Maggie has been a fixture in the crowd.
“It’s so awesome [to have her here]. I try not to look at her during the dance because I know that she’s smiling,” Olson told Us after the September 22 live show, noting how Maggie even wore a “Team Banana ballroom shirt” to the taping.
While Maggie had yet to bring her dad to a show, Olson had high hopes it would happen.
“We need to [have him here]. I think he’ll be at one of these,” he teased.
This story was compiled with the help of AI tools and edited by journalists.
