12. Sandra Bernhard
The most notorious of all Madonna’s female relationships has got to be the one she had with comedian Sandra Bernhard. The two were very chummy, and even appeared together in matching outfits. Bernhard was completely out as a lesbian, so everyone figured that she had her eye on Madonna. Madonna was more than happy to play up to that notion. They made headlines when they appeared together in 1988 on Letterman. They were touchy-feely, and flirted shamelessly with Letterman and each other. After that, everyone considered them to be an item. They always made jokes about hooking up, and talked in innuendo.
Eventually the two of them had a massive falling out. It got so ugly that people thought for sure that it was a break-up between lovers, and not just a disagreement between friends. Madonna shrugged it off soon enough, but Bernhard held a grudge. She slammed Madonna in her performances for years, and even accused the superstar of stealing her girlfriend.
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