2001 - September 2008
Holly Madison dated Hugh Hefner. Madison became one of Hugh Hefner's many girlfriends in 2001 and by 2002 she became his "#1 Girl." She stayed with him until 2008, when she revealed to celebrity website TMZ their affair was over.
Holly Madison dated illusionist Criss Angel. She began dating in November, 2008. After their affair ended, Holly told "People" magazine: "I'm never dating anybody again."
Holly Madison dated Russell Brand. The two were rumored to have had a Vegas fling when they were spotted together with Sean Combs at the Tao night club.
Holly Madison dated Benji Madden. She dated him briefly before breaking up in January, 2010, when Benji decided he didn't want to stay in Las Vegas. Despite the official split, they continued to see each other when they were in the same city for a time.
Holly Madison dated Josh Koscheck.
Holly Madison dated Jack Barakat. "We met through a mutual friend and then somehow somebody retweeted something funny he said on twitter," Madison revealed while promoting the second season of "Holly's World"."So I started following him, and then we started tweeting each other back and forth!"
Holly Madison dated Jesse Waits.
Holly Madison is dating party promoter and CEO of Insomniac Events Pasquale Rotella. Holly announced she was pregnant with her first child. Madison broke the news to Us Weekly. The dad of Holly's baby is boyfriend Pasquale Rotella.
What do you think of Holly Madison's dating history?
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