On Wednesday, the 29-year-old singer dropped the latest episode of their podcast “4D with Demi Lovato,” revealing that they once asked “Schitt’s Creek” star Emily Hampshire out on a date via direct message.
The stars reminisced on their friendship, leading Hampshire, 40, to disclose how their paths crossed.
“You slid in my DMs and you said, ‘Hey, I like you on the show. We should kick it some time,'” the sitcom star recalled. “And then you said, below it, ‘And by kick it, I mean go on a date. I find you attractive.’ You made it clear it was a date. And I loved that because sometimes that’s confusing.”
The actress joked that because she’s “decades older” than Lovato, she had to research the meaning of “kick it.”
Because of their age difference, Hampshire was unsure that she and Lovato would even find the same things funny.
“You also said, ‘Think of Sarah Paulson and Holland Taylor.’ And then right after you were like, ‘I don’t mean you’re the Holland Taylor!'” the actress remembered, per Yahoo. The quip was humorous as it’s a reference to the relationship between actresses Sarah Paulson, 46, and Holland Taylor, 78, who boast a 32-year age difference.
“I thought it was the funniest thing in the whole world because I was a Holland Taylor in that situation,” joked Hampshire. “Proud to be.”
Lovato then explained what was going through her mind when they sent the actress the messages.
“A non-binary person can dream. And they, she—I was a ‘she’ at the time—she was dreaming big. I was like, ‘What’s the worst that could happen?'” the “Anyone” singer said. “And I made a really good friend. You’re a dope friend, and I’m happy we became friends.”
“Me too,” Hampshire agreed. “I wish you weren’t 29!”
The “Schitt’s Creek” star was previously married to a man named Matthew Smith from 2006-2014. She was engaged to singer-songwriter Teddy Geiger until 2019.
Lovato has been linked to a number of famous names including Wilmer Valderrama, Trace Cyrus, Joe Jonas, Max Ehrich and more.