Jackson Olson is painting a wholesome picture — meeting the legendary Pat Sajak went smoothly, he's being his 'authentic self,' and everything is golden. The couple is long-distance but making it work between Savannah and LA because that's what love does.
But here's what's interesting: this is Maggie's FIRST public boyfriend since her split from Scottish actor Ross McCall, who she dated with a glaring 19-year age gap starting in April 2024. That's a notable pattern worth noting — especially when you're the daughter of one of TV's most recognizable game show hosts.
Jackson Olson, 28, hard-launched his relationship with Maggie Sajak, 31, on Instagram last week with a Disneyland PDA photo captioned 'Applications closed.' He confirmed to US Weekly (May 2, 2026) that he met Pat Sajak, 79, and called him 'a great guy,' while admitting he's nervous during games when Maggie watches from the stands.
Pat Sajak's approval might be secured, but let's see if this long-distance romance between a viral baseball star and a TV personality can actually survive the distance — and the spotlight that comes with being wheel of fortune royalty.
Jackson Olson is officially in the inner circle. The Savannah Bananas baseball star confirmed to US Weekly on Friday that he's met Maggie Sajak's famous father, Pat Sajak — and according to him, it went better than anyone's nervous first meeting could hope to go. 'Everybody's nervous to meet the father of the person they're dating, or mother or both,' Olson explained, showing surprising emotional awareness for a guy who makes his living doing synchronized baseball tricks for crowds.
The 28-year-old athlete called Pat Sajak, 79, 'a great guy,' which is exactly what you'd say when asked about meeting your girlfriend's dad if you wanted to avoid drama. Whether that's strategic PR language or genuine warmth remains deliciously unclear. The couple hard-launched their romance last week with a PDA-filled Disneyland selfie, captioning their joint Instagram post simply: 'Applications closed.' It's a clever bit of wordplay for someone who works in entertainment-adjacent sports — though let's be real, dating Maggie Sajak probably did require filling out some kind of application.
She's the social media correspondent for Wheel of Fortune, a job she's held since fall 2021, and her father is one of the most recognizable game show hosts in television history. Olson also opened up about being his 'authentic self' around Pat — a claim that tracks with how he's presented himself publicly as 'a weird' and 'very out there person.' I'm happy that I'm able to be myself truly in every aspect now,' he told the outlet.
But here's what makes this interesting: Olson admitted he's extra nervous during Savannah Bananas games when Maggie is watching from the stands. Obviously, I want to make my parents proud … [and] now I want to make Maggie proud, I want to make my teammates proud,' he shared. The relationship does face one significant obstacle — geography.
Olson lives in Savannah, Georgia while Maggie is based in Los Angeles, California. The distance hasn't stopped them from making 'really cool experiences happen,' according to Olson, who seems committed to the romance despite being thousands of miles apart. You only get one chance at a start of a relationship,' he noted, which sounds like something a guy says when he's aware the clock is ticking on a long-distance situation.
This hard launch comes after Maggie's previous high-profile relationship with Scottish actor Ross McCall ended quietly. The exes, who shared a 19-year age gap, were first linked in April 2024 when they were spotted kissing and holding hands during a walk in Los Angeles. Whether Olson represents a fresh start or simply a different type of partner entirely remains to be seen — but one thing's certain: the Savannah Bananas star isn't hiding from this relationship anymore.
