Hugh Hefner and his girlfriends, 2009
Hugh Hefner and Barbi Benton, 1973
Sondra Theodore and Hugh Hefner, 1977
Shannon Tweed and Hugh Hefner, 1983
Hugh Hefner and Carrie Leigh, mid-'80s
Kimberly Conrad, Hugh Hefner, and their sons, 1998
Brande Roderick and Hugh Hefner, 2001
Tina Jordan and Hugh Hefner, 2002 
Hugh Hefner and the Girls Next Door, 2007
Hef's Girlfriends | 1 of 9
Michael Bezjian/WireImage
Crystal Harris, Hugh Hefner, Karissa Shannon, and Kristina Shannon, May 16, 2009
Think you can do better? Respond with your own gallery now!Hef's Girlfriends
Hugh Hefner and his girlfriends
We get that they're twins, but we were still a little bummed out to hear that Hugh Hefner can't tell two of his three girlfriends apart. Honestly, if you look quickly at a photo of Hef's latest batch of ladies, it's even a bit hard to distinguish 22-year-old Crystal Harris from the 19-year-old Shannon sisters. But luckily for Hef, either Karissa or Kristina has a small mark on her neck that helps him crack the bombshell code.
Do they really look that much alike? Or is the world's most legendary bachelor just getting that old? Maybe it's the age difference; we know we can't always tell friends' babies apart, and there's a much shorter time span between us and newborns and Hef and his babes.
Then again, maybe Hef's still pining away for his former steadies, "The Girls Next Door": Holly Madison, Bridget Marquardt, and Kendra Wilkinson. The trio left the Playboy Mansion last year. But at age 83, Hef has shown us time and time again that he's good at loving the ladies and then moving on. Take a look at some of the women he's wooed over the years.
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Comments
joegolf46
June 30, 2009 - 05:44 AM GMT
His taste in women has gone down just like the quality of his magazine's centerfolds.Too bad they have to airbrush constantly these days....When was the last time Playboy did any meaningful story writing??
Alas,he is just an old man trying to recapture his youth through phony,shallow eye candy these days.Sorry,Hef.You're just not 'hip' any more.
kronosx8
June 29, 2009 - 11:22 PM GMT
jjjeeeaaalllooouuusss, he's what 80 now? Older maybe? and you think he's going to regret his life? His life was and is amazing and I guarentee he doesn't regret any of it. Maybe he never found true love but maybe we don't all find it in this world. As for living in sin, who are you to judge, who is god to judge for that matter. If you make a car and it breaks down, do you blame the car or the mechanic and gave the mechanical flaws? Same logic applies, dumb religious nuts.
Manu Dimanu
June 29, 2009 - 09:35 PM GMT
Yeah Heff, show more of dem boobies to the rest of the world. Thanks a million......
kulka
June 29, 2009 - 09:25 PM GMT
What a life...the dude has no idea what it means to be with someone who you love and trust. Waisted life..what for? Money and Fame?? Gross!
Korq
June 29, 2009 - 09:16 PM GMT
Gotta admit its pretty amazing what this guy has accomplished with his life. Really takes a special kind of person to do what he's done.
mlynch481
June 29, 2009 - 08:26 PM GMT
It is a real shame that you all cannot see the sin and fornication that this man has committed over the years. If he does not change his ways before he dies his eternal home in hell will be nothing like the lavish lifestyle he has lived on earth.
sandberg
June 29, 2009 - 01:10 PM GMT
There will always be those with money and fame who buy sex and there will always be young girls stupid and vulnerable enough to sell it. How sad and shallow!
Lordparsnip
June 29, 2009 - 08:06 AM GMT
The guy has lost his taste in nice women..he seemed to have good taste in the earlier pictures, now all the girls he's with all look the same, they only appear to regular joes to be goodlooking because of their fake hair,rack,colouring ,but these are NOT naturally good-looking women,you can tell by their faces..give me a natural woman anyday,nothing better than that..can't stand that out of porportion lollipop head look. I'm a fairly attractive 35 year old dude who would not find it overly difficult to find a woman with fake blonde hair and breasts,but it doesn't do anything for me. Prefer a naturally curvy soft brunette who hasn't got two footballs stuck to her chest and whose tan doesn't rub off on your sheets ..Poor old Hef's got the idea that younger is better than slightly older,purely to say he can pull em, I'd prefer a decent looking woman of 40 with a sense of humour rather than a 21 year old bimbo. Sad when a guy just pulls young women to impress their friends,rather than be with someone you really wanna be with and laugh with ..what a waste of time and energy.. Good luck to him but if you ask me he'd be better off being with a woman who stimulates him upstairs as well as downstairs..
ktypestar
June 29, 2009 - 07:26 AM GMT
In addition, I always thought Hef made a good choice picking Kimberly Conrad to be his wife, as well as the mother of his children....
ktypestar
June 29, 2009 - 07:19 AM GMT
Having been lucky enough to have once dated a Playboy model, I will say this:
1. It gives a guy almost unlimited access to anywhere he wants to go in L.A.
2. Keeping this in mind, that guy's "networking" just reached a higher level.
3. It's a real ego boost to watch other guys drool and slobber over the Playboy model that you're now with...