Kaite Cleary is married, so unless you’ve got a hot scoop that she’s two timing her husband, I think you’re off on that one. (Yes they were photographed together in a nightclub in France). Probably just banged, not dating.
While I admire his zeal, I’ve gotta wonder why he hasn’t been able to find a “keeper” out of this bevy of beauties.
This ri chea [en.wikipedia.org]
Because why buy the perfect cow when you’re getting eternally youthful, sweet, delicious milk for free?
You’re looking at a list of hot women/supermodels and wonder why he didn’t stop at one to forgo the others?
I think Leonardo is living exactly like someone with his status and wealth should. Not marry some random model or actress, have a child and pretend it’s all he ever wanted while he could tour the world on mega yachts and bang any model he wants.
Not sayin’ I don’t admire the guy for dipping his wick. Just wondering why (when you’ve got the pick of the crop) he can’t pick one. Maybe Kungfu says it best.
He’ll probably do the George Clooney thing and settle down with a intelligent, pretty woman who holds his attention. If you can fuck *almost* any supermodel you want (he’s gotten rejected by Candice Swanepoel and Karlie Kloss – why do I know this) why would you spend the rest of your life with one? Beauty fades and shit.
To paraphrase a line from Money by Martin Amis: because there’s one thing your girl can’t give you; a change from your girl.
Helena Christensen? Man, she was something else back in the supermodel boom days.
What an awesome asshole. Who’s jealous? This guy!
Is there a stronger word than envious? I’m feeling whatever that is.
Bar Refaeli FTW
Gotta agree, looks he he peaked there…
Yea, shouldn’t stopped there man
They all seem to be fashion models, which is kind of an odd choice. They look more like accessories than actual girlfriends.
Yeah, I’m not sure “dating” is the right word in this context. More like fuck buddies until he gets tired of their company.
The curve definitely peaked at Gisele/Bar and then went down imho..
I don’t know about that, Heatherton and Lively aren’t really “down”, maybe a lateral move if anything.
Leo Or Jeter?
Was just gonna post the same question.
Minka Kelly trumps all, so yeah, Jeter.
Plus Jordana Brewster, Adriana Lima, Jessica Biel, Jessica Alba and Scarlett Johansson. Definetly Jeter.
Leo and I’m a Yankee fan
Man this is depressing.
I got to be honest, I think Jeter has got Leo beat.
Die. Die die die die.
Tom Brady, how does Leo’s dick taste?
so dumb but i cracked up at this
Doesn’t it cure cancer?
So… we’re not going to do an official ranking here?
Meh, I’ve dated at least half of those women myself.
And by “dated” I of course mean “touched myself while thinking about them.”
“Leo, Can I smell you’re dick?”
Maybe it’s just me, but to me, it sure seems like Leonardo DiCaprio enjoys dating beautiful women.
Oh my God, I think you’re onto something!
The man has slated some top shelf pussy.
You know what? Good for you Leo. Good for you.
I could have sworn he was till with Toni Garrn, which I guess meant he cheated on her with a plane full of women. I also read something about how he’s with a lot of women, but he only chooses the model types to show out in public. Gotta be good for the ole self esteem!
Side note: he must have dick warts. Every celebrity must have warts of some kind.
They’re called “love bumps” and like with any other STD, if you just ignore them they go away.
This guy definitely has a type.
Welp, this ruined Friday. Will be spending all weekend on a treadmill.
Not even gonna lie, if I were DiCaprio, I’d be rolling onto the red carpet at events with two hot girls. Minimum. I mean, dude is pretty much THE MAN so it should be basically no problem to live a non-stop threesome where he just rotates girls in and out the moment any of them get too attached to him.
All these women must be really dumb. So good looking, so beautiful, so famous, so rich and they all settled for a manwhore. OR maybe they must have just used him to get into the publics eye and increase their profile. Any way he is old and ugly now……….so he will have to start paying for it if he is not already doing that like Charlie Sheen.