How does Hugh Hefner's relationships work?

Answer 1

Each of Hugh Hefner's girlfriends are, obviously, aware of one another. They all must obviously accept this arrangement. They all know that he does not care for monogamy also and they are completely aware of his past and also his current lifestyle.

He supports each of them and provides opportunities for all of them. He has the money to do so.

In the world of Hef, his girlfriends do have "rankings" but he still loves them all equally. Holly Madison is girlfriend number one. Being girlfriend one means extra special privileges. Girlfriend one is about the equality of anyone else's (only) significant other. Number one shares the bed, generally poses in photos on one side of him alone, and has more responsibility.

Bridget is girlfriend two and Kendra is girlfriend three. Two and three are about the equivalence of, say, your "girls on the side" that your significant other doesn't mind (as if that would ever happen, eh?) These two generally pose in photographs on the opposite side of Hef from girlfriend one and stand together. Each of these girlfriends have their own rooms in the mansion, but I'm sure they both also share the bed on occasion with Hef or both Holly and Hef. These girls generally have less of responsibility or "weight" to pull, but Hef says that he loves these girls just the same.

Even though they all say they genuinely care for him, I'm sure that in the beginning of the relationship(s) the celebrity status and amount of money (and also the market) was exciting to each of the girls and probably the driving force to give the relationship(s) a try to start with. Eventually, I'm sure each of them did develop a real connection and feelings for him.

You can learn a lot by watching Girls Next Door on E! about the way the relationship(s) work, and who does what. There was also a special that reruns on E! occasionally called E! True Holleywood Stories: Hugh Hefner that has a lot of similar information. Try reading any of the biographies that are available if you're interested. There's also talk of a movie in the works similar to that of Walk the Line about Hef's life.