In August of 2012, she announced that they were going to be expecting a baby together.
But the reality was, when Madison was a nobody working at Hooters, she was more than willing to lay down for the opportunity to get into Hefner's Mansion aka bed.
While we are talking about Holly Madison beauty, skills, and professional life, we want to now take you on a ride through a Holly Madison bikini photo gallery.
The 41-year-old sat down with podcast host Alexandra Cooper for a very candid chat about her relationship with the infamous womanizer.
The flaunting of this old man having beautiful, young, blonde, busty women falling all over his home and giving him attention may just be somewhat of a cliché.
Then they broke up, and her career kinda went downhill, but she's had her share of successful, bikini-donning ventures.