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You know I watch this show, and I think that this is just a contracted arrangement. For the first few episodes, I didn't even realize that Bridgette and Kendra were his girlfriends. I thought they were just playmates who lived in the house, posed for the mag, and made public appearances for Playboy. Holly is the only one who spends time alone w/him, and I'm not sure that he really sees her any different from the other girls. I've never even seen him really kiss any of them, more than a quick peck on the lips. I think he just indulges Holly because she up and caught feelings. More than anything it seems like a group of women that live in the mansion and accompany Heff out in public in order to promote the Playboy lifestyle, in exchange for hopefully one day making it into the magazine (which they just did). I really don't think its anything personal. However, I must say that in keeping Heff's image up, the girls are not allowed to date anyone else or to be out of the house later than 9PM w/o him. That sucks.
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