This week on the Howard Stern Show, Demi Lovato confirmed that “Cool for the Summer” was about a specific famous woman whom she’d dated.

When Demi Lovato debuted “Cool for the Summer” in 2015, the LGBTQ+ community was roused to attention regarding her testimony of tasting the cherry and needing to take a bite. She hadn’t yet come out as pansexual, let alone told her mother — but in September of that year, she declined to confirm her pansexuality, instead declaring, “I’m not confirming and I’m definitely not denying. All of my songs are based off of personal experiences. I don’t think there’s anything wrong with experimentation at all.”

A few boyfriends, a trip to Disneyland with DJ Kittens and several statements about human sexuality being fluid later, Demi Lovato told Entertainment Tonight in 2017 that yes, she was open to dating both men and women, a sentiment later reflected in her documentary “Simply Complicated,” in which she spoke directly about her bisexuality.

Howard attempted to cajole Demi Lovato into telling the mystery girl now, but Demi declined, saying “I’m in a relationship now, and that would be inappropriate.” (Demi Lovato is currently dating songwriter Jordan Lutes and says that he is “the one.”)

As per the song, Demi Lovato did indeed tell her mother that she liked girls, too — and her mother said she just wanted Demi to be happy. Lovato relayed to Howard that when she told her stepfather, he said he’d known since hearing “Cool for the Summer,” so we all have that in common. She’d previously spoken about coming out to her parents (which she did in 2017) on Andy Cohen’s radio show.

Robin Quivers noted that now “Cool for the Summer” could become “like the You’re So Vain thing,” with everybody trying to guess who the famous woman is that Lovato took her cool summer trip to paradise with. This is of course correct. YouTube comments present an array of theories:

• “i say katy perry, since demi mentions cherry and katy had a son about cherry chapstick”
• “Miley Cyrus????”
• “Bella Thorne (?)”
• “Cara Delevingne”
• “My guess is Kehlani”
• “I think its Selena Gomez and that’s part of why they stopped being friends.”
• “It was Ivanka”

Nobody mentions Ruby Rose, which is interesting because in 2013, shortly after Demi first appeared on Glee as Santana’s lesbian love interest Dani,  Orange is the New Black‘s Ruby Rose claimed that they’d been involved with Demi Lovato for a two-year period while Demi’s relationship with Wilmer Valderamma was on a break (Wilmer began dating Demi when she was only 17 and he was 29). In March of 2014, Demi Lovato got an undercut. Also in March of 2014, Demi Lovato filmed a music video at Pride, which she’d reflect on seven years later as a moment when her “queerness was ready to explode.”

In 2015, Lovato addressed the Ruby Rose rumors, declaring that love is fluid and also “Rumors are rumors.. and people are going to spread them. You can believe what you want, but no, I was not in a relationship with her.”

There were indeed also some intense fan theories that Demi Lovato once dated Selena Gomez and that Gomez dated Justin Bieber to cover up their affair. However, it feels safe to say that dating 2008 Justin Bieber is not really the best way to prove that you are not a lesbian, so there’s a lot of holes in that story.

Miley Cyrus and Demi Lovato recently spoke about connecting with each other in friendship as Disney teens, with Miley suggesting their connection was possibly related to being “gay as fuck.” But Demi used to date Miley’s brother, Trace, and there have also been rumors about Demi dating Miley’s sister, Noah Cyrus. So I think like, absolutely not, ultimately.

As for Kehlani, they did make out on stage in 2018, but there’s no feasible way that Demi and Kehlani would’ve connected prior to Demi writing “Cool for the Summer.” Also it was a big year for Demi to be kissing girls and non-binary people on stage.

As for Katy Perry, well — I simply don’t think so! But this feels like as good of a place as any to just generally note the “Year of the Lesbian” t-shirt situation.

Finally, Cara Delevingne, I understand why she’d be thrown out there as a guess — just looking at the statistics — but again simply don’t think so. It also feels unlikely Cara herself would’ve kept this secret.

Ultimately, there’s only two people who know for sure who “Cool for the Summer” was about, Demi Lovato and the mystery woman, who has not yet left a comment on YouTube, a noted repository of accurate, well-researched information.

Lovato at the MTV VMAs on September 12, 2023 (Photo by Mike Coppola/Getty Images for MTV)

Demi Lovato also told Howard Stern that historically, she’s been rejected more often by women than by men. “I think what’s happened in the past is they just want a hookup,” she told Howard, “and I actually wanted something more serious, so it ends up not working.”

“Isn’t that weird? You would think the opposite,” Stern responded. “That guys would just want the hookup. And you get tremendously hurt by that, I’m sure?”

“Yeah, especially when you like the girl, it was definitely painful,” Lovato agreed.

“I’d like to meet the girl that just wanted a one-nighter with you,” Stern said.

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