The flirtation in question occurred in 2015 during an installment of Cyrus’s Happy Hippie Presents: Backyard Sessions on YouTube, in which the pair of pop stars performed a cover of Crowded House’s “Don’t Dream It’s Over.” Their duet has since received over 114 million views since its release. Cyrus, 30, reflected on the funny moment and the long-lasting friendship she shares with Grande in one of the latest videos in her TikTok series “Used To Be Young.”
“This is as serious as it can be, me and Ariana Grande performing in onesies in the backyard,” the “Flowers” singer quipped as she showed viewers a clip of the performance. The two were seen engaging in banter until Cyrus at the time flirtatiously remarked, “Whatever you are, it’s probably the cutest mouse bear thing I’ve ever seen.”
Grande, for her part, was visibly flustered and had been so thrown off by Cyrus’ flirting, that she missed her cue. Immediately, Cyrus reassured the Wicked star and the two shortly laughed it off, “It’s fine, we can just riff on it! Sorry, I was f***ing you up. Sorry, I was flirting, sorry!”
“I was flirting with her, and she was a little scared. We were having fun!” Cyrus looked back on their banter, reflecting that over the years, Grande has been a “real friend” to her. “There’s never been a time where I’ve asked her to do something that was important to me and she didn’t come through, and the same thing me with her,” she added.
Back in 2018, Cyrus spoke about what set her friendship with Grande apart from other famous friendships in an interview on The Howard Stern Show, saying: “I feel like people have these friendships that are really based on, ‘Hey, you know, you’re famous. I’m famous, and if we come together, we’re like so famous. It’s really stupid, and it’s not really a real friendship, and you probably talk where everyone can see it more than you talk privately.”
She continued, “If I ever see anything, and I never even know if it’s true or not, ‘cause people say crazy s*** about me all the time, but I’ll just text her and say, ‘You know, I’m really thinking about you, and if you ever want to talk to me…’”
Beyond their “Don’t Dream It’s Over” cover, the two stars have collaborated numerous times over the course of their respective careers, but the cover marked their very first. At Grande’s 2017 One Love Manchester benefit concert, aiding victims of the Manchester Arena bombing that followed her then-recent concert, the duo performed another rendition of “Don’t Dream It’s Over” for fans.
In 2019, the famous friends linked up for a collaboration including Lana Del Rey called “Don’t Call Me Angel” for the Charlie’s Angels soundtrack that Grande was tasked to curate in honor of the reboot released that year.