Jimmy Kimmel helped Olivia Rodrigo cross babysitting off her bucket list on Wednesday night—then kept adding kids. And sugar.
Rodrigo was on Jimmy Kimmel Live! promoting her new album You Seem Pretty Sad for a Girl So in Love when Kimmel set up the bit.
“There were things you missed out on in life,” he said at the desk. “We discussed one of those things last time you were here. I vowed silently to myself—many are calling me the next Oprah, the new Oprah—to make that wish, that dream, come true.”
That led to a pre-taped segment in which Kimmel reminded Rodrigo what she’d told him she’d always wanted to do: babysit.
At first, it looked manageable enough. Kimmel introduced Rodrigo to two preschoolers, Hattie and Max, and left her to it. Moments later, he returned with two more. Then another batch. And another. Before long, Rodrigo was trying to wrangle a room full of kids as they climbed on furniture, played hide-and-seek, showed off tricks, and competed for her attention.
Kimmel was not finished. He kept adding to the group until Rodrigo’s dream gig had turned into a full-blown preschool scrum. Then, as if the situation needed a degree-of-difficulty bonus, he returned with sweets.
“I think I know what might make this even more fun,” Kimmel said. “A lot of sugar!”
The kids took him up on it, and Rodrigo was left to ride out the resulting wave of screaming, running, crying, and general tiny-person mayhem. Kimmel eventually returned to collect the children and pay Rodrigo $14 for her services.
Back in studio, Kimmel congratulated Rodrigo on surviving the experience.
“Well done,” Kimmel said.
“Thanks,” Rodrigo replied.
Then he offered to help fulfill any other youthful milestones she may have missed.
“Any other dreams you might have?” he asked. “Maybe have your wisdom teeth pulled? Anesthesia?”
Watch the full segment below:
