Celebrity loves and lovers. Who is Holly Madison dating? Who Holly Madison dated; list of Holly Madison loves, ex boyfriends; breakup rumors. With all the high profile men Holly Madison has hooked up with, it's amazing to think she's not yet on the list of celebrities with sex tapes. Not that a celebrity sex tape is such a big deal for someone that's been attached to Hugh Hefner, but there just seems to be a weird flurry of activity attached to all the celeb sex tapes that's unlike any other celeb scandals. For now, Madison is celeb sex tape free, but with this roster of men, who knows whan that will change? The loves and relationships of Holly Madison, listed by most recent.