Olivia Rodrigo says she wishes she was a babysitter before rise to fame: ‘A dream I’ve never accomplished’

Olivia Rodrigo has shared her regrets about missing out on another career before her rise to fame.

The singer, 20, spoke candidly about her successful music career during an appearance on Jimmy Kimmel Live on 24 October. Speaking to Rodrigo, Jimmy Kimmel said that he heard from their mutual friend that one of her “regrets” was not having the chance to babysit, since she became famous at a young age.

In response, Rodrigo acknowledged how being a babysitter is something she’s always thought about. “That’s one of my biggest dreams that I’ve never accomplished,” she said. “I would really love to be a babysitter.”

The “Vampire” singer even offered to work for Kimmel, as he shares two young children – Jane, eight, and Jane, five, with his wife, Molly McNearney.

“I love kids, so if you are ever in the market for a babysitter, hit me up,” she quipped. The TV host then followed up by asking her how much she’d charge as a babysitter, given her success in the industry.

“We could make that happen, no problem, although I’m guessing you would have to charge like $1,800 an hour or something,” he said. “Would you cut us a deal?”

Rodrigo went on to assure Kimmel that he wouldn’t have to pay her a huge amount for babysitting, quipping: “No, for you, I’d give you a discount.”

The singer first rose to fame in 2019, when she starred in the hit Disney + show, High School Musical: The Musical: The Series. After writing music for the program, she went on to release her first single, “Drivers License”, in January 2021. At the time, the song quickly debuted at number 1 on the Billboard Hot 100, before she released her first highly-anticipated album, Sour, in May of that year.

Since then, the “good 4 u” singer – who released her second album, Guts, in September – has spoken candidly about her rise to fame. When Rodrigo appeared on the cover of Interview Magazine in September, Phoebe Bridgers asked her how she felt about her transition from being a teenager writing songs to “becoming famous for being authentically yourself”.

In response, Rodrigo said she thought about that transition “all the time,” before reflecting on her upbringing and how it’s still similar to her fans, regardless of her success in the entertainment industry.

“This sounds weird to say, but I think over time, I’ve realised that I’m really not that special. My life is just so - I was home-schooled and all of this stuff happened in my career, but then I really boiled my problems down and I’m like: ‘Oh, they’re just 19-year-old, 20-year-old problems in a different environment,’” she said. “If you speak honestly about any experience, then someone is going to find truth in it.”

Rodrigo has also confessed that, after the blockbuster success of her debut album, she got involved in relationships that may not have been a good idea. During an interview with The New York Times in August, the “get him back!” singer explained that the success of Sour led her to feel as though there was pressure to meet certain expectations.

“I had such a desire to live and experience things and make mistakes and grow after Sour came out, I kind of felt this pressure to be this girl that I thought everyone expected me to be,” she said. “And I think because of that pressure, maybe I did things that maybe I shouldn’t have - dated people that I shouldn’t have.”