Madonna’s same-sex dalliances is coming back under the microscope again.While the Queen of Pop’s romantic entanglements are routinely the subject of gossip and interest, it’s been a minute since one of her sapphic interludes made headlines.In the ’80s, Madonna enjoyed a close friendship with comedian Sandra Bernhard. The pair infamously teased their bond during an appearance on David Letterman wearing similar outfits.Subscribe to our newsletter for a refreshing cocktail (or mocktail) of LGBTQ+ entertainment and pop culture, served up with a side of eye-candy.madonna telling david letterman he can hang out with her and sandra bernhard only if he gets a sex change, 1988 pic.twitter.com/HfmQdZj0cEThe extent of their relationship has never been fully divulged since Madonna and Bernhard soon had a falling out and haven’t spoken to each other in decades.
Rumors have always suggested the rift may have been caused by Madonna allegedly starting a fling with Ingrid Casares, who had been Bernhard’s girlfriend.It’s all hearsay, but Casares’ image did appear in a montage of former lovers during Madonna’s Celebration World Tour, one of the first public confirmations of their romance. Casares also remains good friends with Madonna and was a “Vogue” guest judge during one of the Miami stops on the tour.Ingrid Casares serving as the guest “Vogue” judge for Madonna at The Celebration Tour in Miami, Florida, April 6, 2024.
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