"Playdate with Destiny" is a 2020 short film starring Maggie. It was announced on February 27, 2020 on the show’s official Instagram page.
Onward opened in theaters on March 6, 2020. Unlike The Simpsons Movieand The Longest Daycare (the former was rated PG-13 by the MPAA while the latter was rated PG), the short film is rated G by the MPAA, making it more family-oriented than that film. This is the second short film starring Maggie Simpson after “The Longest Daycare”. The short film was later released for streaming on Disney+ on April 10, 2020.
Marge Simpson takes Maggie to a park for toddlers. When another baby goes down the slide and almost crashes into her, she is saved by a boy named Hudson. Maggie becomes smitten with Hudson, and the two play games together, which Maggie fantasizes as a whirlwind romance. At the end of the day, Maggie gives Hudson her blue bow to remember her by, and that night she dreams about Hudson in her sleep. The next day, Homer looks after Maggie instead of Marge, and he takes her to a different park with food trucks. Maggie sees Hudson waiting for her in the adjacent park and desperately tries to get his attention, but Homer pulls her away before she can. That night, Maggie drowns her sorrows in baby formula and becomes despondent over not being able to see Hudson.
The next day, Homer babysits Maggie again. Before he can take her to the same park as the day before, Maggie grabs hold of the car's steering wheel and steers it into the park where she met Hudson. She sees him boarding a train for children and runs across the park to catch up with him. When Hudson sees Maggie trying to catch up with the train, he reaches out to her with her blue bow, but she fails to catch up before the train pulls away out of her reach. Maggie believes Hudson is gone forever, but the train (running on a circular closed track) loops around to the station at which it started. Maggie and Hudson reunite on the train's cowcatcher, and they exchange pacifiers (in lieu of sharing a kiss).