Where did Maggie Sajak and Jackson Olson reveal their relationship?

Maggie Sajak and Jackson Olson revealed their relationship with a photo shared from a trip to Disneyland.

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Maggie Sajak's New Beau Revealed!

Q: Who did Maggie Sajak debut her relationship with?

Maggie Sajak debuted her relationship with Jackson Olson, a player for the Savannah Bananas baseball team.

Q: Who was Maggie Sajak previously linked to?

Maggie Sajak was previously linked to Scottish actor Ross McCall.

21 Apr

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Summary

Maggie Sajak and Jackson Olson debuted their relationship at Disneyland.
Olson had previously humorously advertised for a girlfriend on social media.
Maggie Sajak was previously linked to actor Ross McCall.

Maggie Sajak, daughter of Wheel of Fortune host Pat Sajak, has publicly confirmed her new relationship with Jackson Olson, a player for the Savannah Bananas baseball team. Sajak, 31, shared a photo on Instagram on April 21, 2026, cuddling with Olson, 28, at Disneyland. Olson playfully captioned the post, "Applications closed✅."

This announcement comes after Olson humorously posted a "boyfriend application" in December 2025, seeking a girlfriend and promising a trip to Disneyland. His Savannah Bananas teammates shared their enthusiastic reactions to the news.

Sajak was previously linked to Scottish actor Ross McCall. In April 2024, photos surfaced of them together in Los Angeles. Their romance reportedly began after months of flirty online interactions.

Maggie Sajak has a notable presence on Wheel of Fortune, having served as a "special letter toucher" and temporarily filling in for Vanna White in 2019 when Pat Sajak underwent surgery. Pat Sajak and his wife Lesly Brown have two children: Patrick, 35, a physician, and Maggie, born in 1995.

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