14. Sandra Bernhard
The outrageous, outspoken, and out-there actress, author, and singer, Sandra Bernhard, is an open book about her bisexuality and pretty much everything else. One thing she’s discussed over the years is her past relationship with her longtime gal pal, Madonna. Apparently, the two were romantically linked back in the 1980s, although Bernhard may have crossed the “Borderline” with that fling. Whether Madge was just dipping her toe in the “lady pond” or had true feelings for Bernhard is something only the two of them know, although the ladies made for an unusual, yet somehow, perfect match. As you’ll read on, Bernhard will not have been the last lady that Madonna would “Live to Tell” about, and who knows if Bernhard was her first either? Certainly, a world of attention-seeking women came out of the woodwork claiming to have known Madonna when she was “Like a Virgin” to getting down with the ladies.