Pat Sajak’s Daughter Maggie Shares New Photos with Boyfriend Jackson Olson After Announcing Relationship

Maggie Sajak is giving fans a glimpse at her Disney adventures with her new boyfriend, Jackson Olson!

On Sunday, April 26, the 31-year-old daughter of retired Wheel of Fortune host Pat Sajak posted an Instagram carousel featuring sweet snaps of the Savannah Bananas player, 28.

In a photo taken from the back, the athlete — wearing a T-shirt, shorts, and a baseball cap — could be seen playing a hoop toss game at Disney. The TV personality also took a turn at the game, including a video of herself getting the ball in the hoop, and her excited reaction afterward. Another snap showed Maggie and Olson’s legs as they both donned white sneakers.

Maggie opted to caption her post with a series of emojis: “💫🏰🏀🍷🐾🌴🎂👟🥰.”

The baseball star took to the comment section, admitting the social media correspondent did better in the game than he did.

“And yes guys, she beat me 😭,” he wrote.

Meanwhile friends and fans also left a slew of comments, gushing over the couple.

“Did I tell you I was obsessed with u guys yet?” one wrote.

“You and @jacksonolson_ are the cutesttt🥹,” a second chimed in.

“cutest couple awarddd,” a third added.

As Star previously reported, the couple hard-launched their relationship on Tuesday, April 21, by sharing a post photo together at the theme park with the caption, “Applications closed ✅,” via a joint Instagram post.

The pair weren’t joking about applications being over, as in December 2025, Olson posted a TikTok video revealing, “I’ve been single for over 5 years. So here is my official 2026 boyfriend application.”

In the video, Olson shared reasons someone might want to date him, including a future trip to Disney, which he made happen!