Olivia Rodrigo Discusses Babysitting Dreams and Robert Smith on Kimmel

They say to be careful what you wish for, and Olivia Rodrigo may have learned that lesson last night on Jimmy Kimmel Live! . On a previous appearance on the late night show, the pop megastar told Jimmy Kimmel she always dreamed of having a regular job, like babysitting. Kimmel took it upon himself to make Rodrigo’s dream come true — and turned it into a nightmare.

Things started off simple enough, with Kimmel introducing Rodrigo to two youngins who just wanted to take pictures in the green room photo booth. But then two more kids joined the party, and they wanted to hop on one leg and jump on the couch. Two more, and blocks got involved. Kimmel just kept coming with more and more kiddos, even sneaking one in while Rodrigo was closing her eyes for hide-and-seek, until there were over a dozen babies to sit. Blocks were being thrown, furniture was being climbed on, and there were even a few tears (which, honestly, Rodrigo handled with aplomb).

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Things got ratcheted up even further when Kimmel introduced every babysitter’s worst nightmare: large amounts of sugar. Rodrigo tried to keep things civil with story time, but when you’ve got a Cheaper by the Dozen -sized group of kids juiced up on brownies, there’s only so much you can do. To her credit, the singer kept her trademark smile throughout and really earned those 14 dollars. Watch the segment below.

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Rodrigo did some actual promo for her new album you seem pretty sad for a girl so in love , out this Friday, as well. She spoke to Kimmel about getting Robert Smith on the track “what’s wrong with me,” noting that her dad is a “diehard super fan” and last weekend’s Primavera Sound was his 30th time seeing The Cure. “He got to talk to Robert because we’re kind of friends now,” Rodrigo told Kimmel. “And the first time he met him, I’ve never seen — my dad’s like, very tough, you know? He’s a dad, he’s a protector. They saw each other and the tears started welling up in his eyes. His screen saver on his phone is a picture of him and Robert… It’s very sweet.”

She went on to perform her single “the cure,” which, of course, has nothing to actually do with The Cure. Watch that performance ahead.

With you seem pretty sad… arriving June 12th, Olivia Rodrigo will head out on her “The Unraveled Tour” beginning in September and stretching through spring 2027. Get tickets here .

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_Originally reported by [Consequence](https://consequence.net/2026/06/olivia-rodrigo-babysitting-jimmy-kimmel/)._