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It was after this relationship ended that she got married to Sean Penn. Vanilla Ice was to follow for a year, and then she would have a relationship that would last from 1991 to 1994.

From 1992 to 1994, she was said to be in yet another relationship with Ingrid Casares, which is among her most popular lesbian relationship.

The Madonna dating timeline stretches back to 1972 when she got into a relationship with Wyn Cooper.

Her relationship history would continue for many years to come.

The series target every body part of a person – all body workout.

No matter how you want to look at it, Madonna has remained one of the most interesting individuals of her time.

Along with the help of her trainer, Madonna released a fitness DVD series named “Hard Candy Fitness’ “.This is not only with the number of men she has dated thus far but also with how they are almost all from different worlds.Born on August 16, 1958, the musician, songwriter, actress, and businesswoman has almost touched the two ends of the world as far as dating is concerned; having been married twice, she has gone out with close to 50 men – or that is how it is rumored.Norris Burroughs and Patrick Hernandez were other men in the line before she went out with Dan Gilroy from 1979 to 1980.From 1980 to 1982, she went out with Stephen Bray, followed by Mark Kamins, Ken Compton, and then Jellybean Benitez from 1982 to 1985. See Also: A Complete List Of Current & Ex-Boyfriends Kendall Jenner Has Dated Following the end of her marriage, Madonna got linked to Warren Beatty from 1989 to 1990, followed by Tony Ward in 1990, then Jose Canseco in 1991.