Jackson Olson and Maggie Sajak hard-launched their relationship in April 2026

NEED TO KNOW

• Maggie Sajak, daughter of Pat Sajak, is a licensed attorney and Wheel of Fortune social correspondent
• She and Savannah Bananas player Jackson Olson announced their relationship in an April 2026 Instagram post
• Sajak is supporting Olson as he competes on season 35 of Dancing with the Stars

Jackson Olson hit a home run with his girlfriend Maggie Sajak.

The popular second baseman for the Savannah Bananas and Wheel of Fortune social correspondent announced that they were dating in April 2026 with a joint post shared to their Instagram accounts.

Since going public with their relationship, they have documented trips to Walt Disney World in Florida and Disney’s Aulani Resort in Hawaii on social media, and even Olson’s hometown in Connecticut.

In July 2026, Sajak, the daughter of Pat Sajak, accompanied Olson to New Milford, Conn., when his hometown little league field was being named after him, allowing him to “show Maggie where I grew up.”

“This was the place where I realized how much I loved baseball. 22 years later and I got to share the moment with my parents, my girlfriend Maggie, and the baseball + softball players of New Milford,” he wrote on Instagram.

So who is Jackson Olson’s girlfriend? Here’s everything to know about Maggie Sajak and her relationship with the baseball player.

She was born in 1995

Sajak was born on Jan. 5, 1995, to parents Pat Sajak and Lesly Brown, joining older brother Patrick, who was born in 1990. Although Pat’s job with Wheel of Fortune was based in Los Angeles, Maggie was raised across the country in a “tight knit community” in Maryland.

“I grew up in Maryland. I went out to California a decent amount, but went to school in Maryland,” she told Billboard in 2013.

“My family lives there, so I’m close to them, which is nice. I went to kindergarten there, and everyone went on from there to high school. It’s a tight knit community,” she continued.

She graduated from Princeton

Maggie graduated from Princeton University, followed by a postgraduate program at Columbia University. She went on to graduate from Georgetown University and become a licensed attorney in California.

She works for Wheel of Fortune

Like her father, Sajak is making a name for herself on the set of Wheel of Fortune. Over 25 years after making her debut on the game show as a 1-year-old, she joined the long-running series in 2021 as the social correspondent.

Following Pat’s announcement in June 2023 that season 41 would be his last after a four-decade run with the show, Maggie was supportive of her dad’s decision.

“It’s so much fun working with my dad…and we’re looking forward to even more fun in Season 41,” she wrote on her Instagram Stories, along with a repost of Pat’s statement.

She started dating Olson in 2026

Olson and Sajak surprised their fans when they hard-launched their romance with a joint Instagram post in April 2026.

The couple were all smiles in the photo while posing in front of Walt Disney World’s Cinderella Castle in Magic Kingdom. “Applications closed✅,” read the caption.

The caption was a reference to the “boyfriend application” video that Olson had posted to social media in December 2025, listing facts about himself, including his “unhealthy obsession with musicals” and his “diet of a 12-year-old,” while One Direction’s “Kiss You” played.

She’s “excited” to watch Jackson on DWTS

Less than a month after the couple launched their relationship, it was announced that Olson would be a contestant on Dancing with the Stars season 35. During an interview at the ESPY Awards 2026, Sajak made it clear that her boyfriend would be getting her votes this season.

“He crushes everything he sets his mind to,” she told USA Sports‘ Renee Montgomery. “I’m excited to see him crush it in the ballroom.”

Sajak added, “I’m just so excited to support him through this whole journey. It’s going to be amazing.”

A few months later, Sajak was in the audience to witness Olson make his DWTS debut on Sept. 15.

“Seeing @jacksonolson_ chase his dreams and shine in the ballroom is the joy of a lifetime. Keep watching, keep voting…he’s just getting started!!!!!” she captioned an Instagram post.

She’s released music

Sajak’s music career may have started as a teenager, but her love for playing instruments began much earlier.

The then-college sophomore told Teen Vogue in 2013 that she was “seven or eight” when she started playing a “mini acoustic guitar,” gifted to her by her grandparents until she received a “real guitar” from them on her 13th birthday.

She explained, “It’s always been a dream of mine to be a singer. When I started playing guitar and performing more often, my passion for music became a top priority. With each new song I record and music video I release, I see my dreams becoming a reality.”

Her singles include “First Kiss,” “Wild Boy,” “Live Out Loud” and “If I Was Gonna Go.”

Olson had “given up” on love before meeting Sajak

Olson wasn’t sure if he would find “a girl he wanted to be with” before he and Sajak connected.

Along with a photo of the couple in front of Spaceship Earth in Walt Disney World, Olson shared on Instagram that he was looking for someone “to have the same morals” as he does and “to have a kind soul.”

He continued, “To like me for me and not for what I post on social media. To love their family and enjoy spending time with them. To not take life so seriously and not care what other people think.”

Olson shared that he “found all of that and more with Maggie,” and offered advice for anyone in a similar situation: that the “moral of the story” is to not “rush it” and “never settle.”

“I’ve never met someone I thought I could spend every day with until I met her. And a major reason why is because we can be our true selves around each other,” he wrote. “If you think you haven’t found ‘the one’ yet and that it’s ‘too late’ trust me it’s not. Sometimes life only gives you what you truly want when you’ve been patient enough.”

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