Maggie Sajak & Jackson Olson Go On Sweet Disney Date

Maggie Sajak and social media star Jackson Olson are giving fans another look at their relationship. The couple recently shared a Disney World date night on Instagram, posting clips of rides, snacks, and a romantic dinner together, with Olson joking in the caption, “No more single rider.” 

Maggie, 31, is the daughter of former Wheel of Fortune host Pat Sajak. She has built her own career as a Wheel of Fortune social media correspondent and country music singer. Jackson, 28, plays for the viral baseball entertainment team Savannah Bananas and has amassed a large following on social media thanks to his on-field dance routines and personality-driven content. 

The pair first went public with their relationship in April after sharing a Disney-themed post together. Their romance drew extra attention because Olson had gone viral earlier this year for posting a humorous “boyfriend application” video after being single for more than five years. It seems the search is officially over.