In the past, Madison has stated that she wanted to marry Hefner and have his children. During an interview at the Playmate of the Year luncheon in May 2008, Hefner stated, "I love Holly very much and I think we’re going to be together the rest of my life, but marriage isn’t part of my puzzle. It’s not a personal thing; I just haven’t had much luck with marriages.
On October 7, 2008,Sexy Madison announced in a video posted on TMZ.com that her relationship with Hefner had ended, but that she, Bridget Marquardt, and Kendra Wilkinson are "still filming stuff together." Hugh Hefner confirmed the breakup stating that, "If Holly says it's over, I guess it's over." Hefner also confirmed that all three girls are committed to a sixth season of The Girls Next Door, and that he plans to find new live-in girlfriends.
In November 2008, Madison began dating illusionist Criss Angel, but the relationship ended in February 2009.Holly was interviewed by People on March 4, 2009, stating "I'm never dating anybody again. I don't need a man. I'm really happy with myself and being with my friends...I'm focused on forwarding my career. I'm working on producing my own shows. Girls Next Door was a great place to start but it was somebody else's show. I'm just ready to move on."In the final episodes of Girls Next Door, which aired in February 2009, Madison made several references to the pending breakup with Hefner.
