So are Charlize Theron & Sean Penn hitting it these days or what?

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Operative words: “hitting it.”

All week, various sites have been all “Charlize Theron and Sean Penn are on vacation together, is that weird? Are they dating?” I ignored it because… I don’t know, I like Charlize and I want to think that she’s smarter than that. It’s one thing to be friends with Sean Penn – in my opinion, that’s bad enough. But to actually, willingly date him or sleep with him? Yikes. But it does look like it’s happening.

The basic timeline is this: Charlize and Sean spent New Year’s Eve in Hawaii, at his vacation home (who knew he had a vacation home in Hawaii?!). Charlize brought along her son Jackson and it seemed like it was just a friends’ vacay. Then Charlize, Jackson and Sean all took the same flight back to LA. Then Sean’s car was parked in Charlize’s driveway (not a euphemism) all night long on the 1st & 2nd. And these new photos of Sean? That’s Sean leaving Charlize’s house yesterday. Add to that “proof” the little fact that People Magazine is now running a “Charlize and Sean are probably dating” story, and I think it’s on.

Are Charlize Theron and Sean Penn more than just friends?

The Oscar winners rang in the New Year together in Hawaii, a source confirms to PEOPLE.

Theron, 38, made a trip to the island without her son, Jackson, 2, to celebrate the holiday by staying at Penn’s beachfront home in Oahu.

Before the clock struck midnight, Penn, 53, spent Tuesday afternoon surfing in the Pacific while the Prometheus star soaked up the sun in a multicolored striped bikini. Later the pair met up with a male friend and sat in the sand, enjoying the water view.

On Wednesday evening, the two were spotted stepping off the same flight at LAX airport. On Thursday, Theron and The Secret Life of Walter Mitty actor both left her house in separate cars, a source reveals.

“Charlize and Sean have been friends for years,” says another source. “They have been spotted out together several times in the past few years. Even when Charlize was dating Stuart [Townsend]. They both had dinner with Sean several times.”

Rumors of a romance between the two first flared up in 2010 after Theron split with Townsend. Most recently, the two were seen acting very flirty at Seth MacFarlane’s Halloween party last October.

“They were laughing and touchy-feely,” says a source.

[From People]

It’s perfectly possible that they’ve been friends for a while and they’re still just friends. But after being in denial about it all week, I think I’ve gotten used to the idea that they’re probably banging. Poor Charlize. Her last boyfriend was, like, Seth Macfarlane. She’s just having a really bad run with boyfriends lately. Who’s better: Seth “Yay, Rape Jokes!” Macfarlane or Sean “Slab of Grizzled Bacon, But Not In A Good Way” Penn?

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Photos courtesy of Fame/Flynet.

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77 Responses to “So are Charlize Theron & Sean Penn hitting it these days or what?”

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  1. Kiddo says:

    Beauty and the beast.

  2. Dreamyk says:

    Charlize is perfection. I must know more about the Penn wang that causes so many beautiful women to discount his troll face.

    • smee says:

      It’s a famous wang.

      • Misulinka says:

        Common, it happens. It happened to me. Amazing sex with not so amazing guy. It turns out to be amazing. It can last, seriously. If the sex is amazing. So, where was I? Yes it happens.

    • Stef Leppard says:

      His troll face and his horrible temper and his narcissism and his history as a wife beater. Ugh.

    • Sullivan says:

      I imagine sexy times with Penn is not unlike stepping on a rusty nail.

    • Becks says:

      Meh… I disagree. I have seen her in person and she is nothing special. She looks waaaay better on film. And she has horrible taste in men, so I don’t understand why people worship her. She is good at what she does, I give her that.

  3. Spooks says:

    God, I hope not. I hope Charlize won’t be with an abuser after what her mother has been trough.

  4. Seapharris7 says:

    I tend to like Charlize, but just like the other females we often question the crazy (Swift, Berry, etc) – she has… pretty diverse taste. Wasn’t she with Stewart for a decade?

  5. smee says:

    I could almost believe “friends” hanging in Hawaii for the holidays, but if the car in the driveway biz is correct…..rutroh!

    She is always dressed so well, even her casual clothes are elegant.

  6. bammer says:

    Is Sean Penn’s son going to be around Jackson? Will he hurl racial slurs if the 2 year old throws a normal tantrum? That poor kid.

  7. Evi says:

    This man is just wrong.
    I don’t care how much humanitarian work he says he does or does or whatever.
    You can do all the humanitarian work you like, but that doesn’t erase the fact that you’re a violent psycho.
    I’ll never forget reading about an incident where he ‘allegedly’ tied Madonna up to a chair and kept her restrained against her will. I think that was written up as being the final straw in their marriage.
    He is a very insecure man. Robin Wright probably sacrificed her career for him because he cannot tolerate his women being more successful and for that alone, Charlize should start running very fast.

  8. Corrie says:

    I’ve heard, word on the street… Charlize has done “a lot” for her Oscar and staying connected with her directors, producers etc. I would’ve never thought of her to be an around the way girl, but I’m hearing louder and louder that that’s the case. This is no surprise here. I’m side eyeing Charlize now. She gives you polished from the outside, but I dont know if that’s a true reflection.

    • JojoAnn says:

      Oh please! Any halfway successful female from film stars to McDonalds branch managers attracts slept-her-way-to-the-top rumors. Its disgusting bs and its how you put ‘uppity’ women in their ‘place’. Unless your source was the guy who rewarded her for sex then its just nonsense that you really shouldnt be disseminating further.

      • Tiffany :) says:

        My thoughts exactly JojoAnn. That is the same exact slur that has been hurled at successful women for the past 60 years. ENOUGH.

    • Jayna says:

      Word on the street. LOL That girl deserved that Oscar all the way. And for an actress of her stature to take that role, I guarantee they were flabbergasted. She was in a long-term relationship when that happened and a strong, intelligent woman. So not even believable. And Patty Jenkins was the director of Monster, a female. She takes a lot of independent movie type roles that are lucky to get her.

      Save the word on the street for the Lindsay Lohan types. At least that is more believable.

    • Sarah says:

      oh come on. do you know how many people vote for the oscar? she really would have done A LOT for it then. dont you think word would have got out more than just “on street” when an actress does over 1000 men? seriousy lol.

      believe it or not some women actually have talent and/work hard to achieve things, all completly without male help.

  9. Mandy says:

    Oh, Charlize….I thought you were better than this.

    • BweeeeeeerayawwwdnBe says:

      As soon as she trashed men and picked up a fashion accessory, I knew she wasn’t.

      • pfeiffer87 says:

        wth are you talking about?!

      • Tiffany says:

        You did not just call her son a fashion accessory. There is something wrong with you.

      • Jaded says:

        She was always vocal about wanting children. There may come a time in a woman’s life, even if she’s not in a relationship with a man, that having a child is the most important thing for her, so she’ll either go the turkey baster route or adopt. She’s wealthy, independent, and is giving a beautiful baby boy a great life, not adding a fashion accessory to her wardrobe.

  10. Maya says:

    I lost some respect for Charlize after she became BFF with the vile, disgusting and disgrace to womankind aka Chelsea Handler.

    But now after seeing her dating Sean – the known woman beater – I am completely off her.

    What kind of mother is she to let a known violent man near her son? Also what kind of daughter is she since her own mother was a domestic violence victim?

    • Evi says:

      If Penn is the charming psycho type, it’s possible. She won’t be the first or last woman to be sucked into the ‘all that was years ago, I learned, I did rehab…but now I’m a changed man’ routine.

      • Plus his rep as an abuser isn’t really widely known–just that he has a horrible temper (which he’s talked about in interviews). When I heard about him abusing Madonna, it was on this site. When I googled it, the closest I got to what happened was that one of Madonna’s former employees wrote about it in a book. And what I heard was that she escaped out of the house (after being held for the three days,etc), ran into some cops, and when they went to go get him (because she was hysterical, screaming–can’t remember if she was visibly bruised or not), he was sitting at the kitchen table, real calm, eating cereal. And when they brought him in and questioned him, he said some bs that he threatened to cut all her hair off if she didn’t sit down and talk with him (I think they had been in a fight), and that he hadn’t hurt her.

        But the thing was, Madonna wouldn’t press charges, and without that the police really couldn’t investigate her (like make her go to the hospital and report her injuries), or him. And this was before they had that law in California, where the DA decides whether or not to press charges, with or without the victim.

        So before all of that, the only thing I heard about Sean Penn’s temper was that he liked to kick the paparazzi. I don’t know if he’s ever abused Robin Wright (I don’t know–they separated legally at least three diff. times), maybe he changed *that* much–but I wouldn’t put it past him to be the emotionally abusive boyfriend at the very least.

        And God, he must be broke, because he’s doing shitty movies like ‘Gangster Squad’.

      • FingerBinger says:

        @ VC I’ve read about Sean Penn assaulting Madonna too, but how did a few hours of abuse become three days? Don’t embellish to make your point. Sean Penn is a jerk, he’s this he’s that, you don’t need to make things up. The truth will suffice.

      • @FingerBinger
        I read that it was three days that he kept her tied up–I don’t know if that’s true or not, because like I said, the only thing written down on paper was this book by a former employee of hers. There were no charges filed. So no need to get snippy. I already said it was something that I READ.

  11. Florc says:

    So, she didn’t last “date” Alex “everyones favorite viking” Skarsgard? I thought he was the last bf.

    • I Want To Live In New York says:

      No I think it was Macfarlane. At least with Macfarlane and Penn there are photos. Wasn’t Alex just rumors.
      If they were together, I don’t understand why she didn’t want to photographed with him. Out of the 3 isn’t he the best?

  12. lisa2 says:

    I don’t know. If you listen to how she talks away from the carpet she is not sweet/innocent. I remember the why she talked when she was promoting that film with Fassbender. All the raunchy talk; and her friendship or whatever with C. Handler. I think she likes a guy that has a bad side, nothing wrong with that. But people give you a gimps into who they are by who they associate with.

    I actually thought that Sean was going to start again with Madonna.

    • Ugh, that was beyond embarrassing. And borderline at times. What if it had been a guy who had been fawning all over an actress, who clearly wasn’t interested in him? I remember when she and Michael did the ‘Actor’s Roundtable’ thing with Tilda Swinton, George Clooney, Viola Davis, and Christopher Plummer—every time he said something, Charlize would echo him like he was the greatest thing since sliced bread. When he did his impressions (at HER prompting), she kept saying ‘amazing’…..she wanted into his pants BAD. And I think she made a joke about his dick at an awards show, correct?

  13. Nicolette says:

    No. Just no!

  14. Sarah says:

    i cant with women like her. why do you think guys like Sean Penn get away with their actions and never think about them? because obviously they have no problem getting laid. why would he think about his behaviour? seems like it doesnt keep women away from him, maybe even makes him more attrative to some.
    i dont think men are dogs, so let me use this example: if a dogs bites people and you pet him he will continue. if a guy behaves like Sean and gets all the women he wants he must think he is treating them right.

    • jinni says:

      Guys like Penn won’t change their ways because they don’t get laid. Those types of guys are so entitled that they will just blame their lack of sex on society and women being b*tches. They than usually take their anger out on innocent women, like the guy a few years back that opened fire on a bunch of women at a gym. The only way for these guys to stop being the way they are is if patriarchal society is removed so that there won’t be a system that nurtures and encourages that sort of behavior in men.

      As for Charlize, I don’t get why everyone has these high opinions or expectations for her. IMHO, she’s never shown herself to be anything but overly aggressive and has always had an air of meanness about her. But, I guess because she can wear haute couture really well and was once infatuated with former site fave Fassbender she was considered some how above other actresses. Oh well.

  15. Cecilia says:

    Charlize seems like a blonde Sandra Bullock to me. What you see is not what you get.

  16. idontknowyouyoudontknowme says:

    Amazing how someone’s status can be elevated just due to their external beauty or assumed elegance and class… She has demonstrated a nasty attitude countless times… imo they are a perfect pair.

  17. FingerBinger says:

    I know we’re all supposed to hate Sean Penn,but I don’t. Both are adults so I don’t get what the big deal is. However, they ARE friends. Interestingly enough he’s also friends with Emma Thompson, Susan Sarandon and many other people that clearly see a decent human being or I’m guessing they wouldn’t be his friend.

    • Kim1 says:

      I guess that,applies to Mel Gibson,Polanski,Woody Allen,Chris Brown,Charlie Sheen,etc
      All decent human beings because their famous friends say so .Good Luck to CharSean

    • Anna Scott says:

      Ha!

    • Anna Scott says:

      FingerBinger says:

      January 3, 2014 at 10:44 am

      I know we’re all supposed to hate Sean Penn,but I don’t. Both are adults so I don’t get what the big deal is. However, they ARE friends. Interestingly enough he’s also friends with Emma Thompson, Susan Sarandon and many other people that clearly see a decent human being or I’m guessing they wouldn’t be his friend.

      Good point!

    • Nikollet says:

      @Fingerbinger I don’t hate him either. His wife-beating of Madonna in the 80’s was disgusting, I abhor domestic violence and find it hard to reconcile my feelings on that with how I feel about him, but there has been no reports that he did the same to Robin Wright, so almost 30 years on I wonder at what point do we let it go?

      He’s definitely got some nasty demons in his past, but he’s also quite the humanitarian these days, with his work in Haiti. He doesn’t just lend his name to a relief organisation like many Hollywood types do, he’s been working to actually get stuff done for 3+ years now. We don’t know his reasons for this, but it seems to me that he genuinely cares. And perhaps he’s trying to do some good to make up for his past. Maybe we should cut the guy some slack.

      • FingerBinger says:

        @ Nikollet Thanks for your comment. First off I think they are just friends. However, Charlize is a grown woman I think she can date whomever she wants to date. People are acting like he’s Jack the Ripper FFS.

      • Well I do think it’s possible that he has changed–he’s cried in interviews about his temper. But it’s affected his son–a while back, his son was freaking out on the paparazzis and called one of them the n word. So his son’s behavior came from somewhere, and hopefully it’s been addressed by BOTH parents. I think now he’s more of a yeller—but that’s still not good. I wouldn’t walk around eggshells, worried that if we get into a fight, he’ll start screaming at me, or worse. I’ve seen pap videos of him running after paparazzi, and kicking them. Hopefully he has changed, but it’s hard to change when you’re older.

  18. Debbie says:

    Oh gross. Oh, gross. Ew ew ew ew ew. That is all.

  19. Jen says:

    I wish Charlize and Alexander Skarsgard had lasted for more than like a week, but if she’s really into Sean Penn, Alex was probably too nice (and not abusive enough) for her.

  20. Fan says:

    He looks miserable. He should go back to Madonna. He looks happier with her.

  21. Anna Scott says:

    Oh for god’s sake!! it’s not like they’re getting married. They probably want to have some fun and move onto other people, should better options come along. She could do much worse.

  22. Sam says:

    He’s been looking for a high profile romance story for months. Is word that he has tried with a number of actresses whom obviously rejected him. It was driving him crazy the fact that Robin Wright has moved on and now she’s engaged with Ben Foster. It surprises me how dumb seems to be Theron, or maybe she was needing a little bit of press too, since none of them have movies on the spotlight.

    • Jayna says:

      When has Charlize ever used her personal life for “press”? She’s extremely private.

      • Sam says:

        yeah right

      • Kim1 says:

        @ Jayna Hiding Jackson until it’s time to promote her film?

      • Tiffany :) says:

        Hiding Jackson until its time to promote her film???? What? It isn’t like we never see him and then she trots him out on the red carpet. We don’t see him at all unless it is a random pap shot. I do think Charlize is very private. She was with that Townsend guy for a very long time, they broke up, but you never found out why. She seems very focused on her work in all of the press about her.

    • FingerBinger says:

      @Sam When has Sean Penn actively pursued press attention for his relationships? Didn’t he allegedly dump ScarJo for getting too serious. If he wanted a high profile relationship wouldn’t he have stayed with her? When he does have movies out he barely does any press or interviews,but now both he Charlize want press attention. Yeah OK. It sounds like you’ve read been reading too many of CDAN made up blind items.

  23. serena says:

    Dear god…….I don’t get why all the ladies are so hung up on him, what the heck is his charm?? He’s such a gross douchebag! And Charlize.. girl, you can do SO MUCH better.. sigh..

  24. bcgirl says:

    omg you guys, what’s it going to take?
    She dated Seth McFarlane, her BFs are Chelsea Handler and Aniston, she’s still cool and smart? She carries around oddly placed immobile baby shoes in a baby carrier with 3 fingers and expects people to believe it’s a 6 month old baby…god, please. Do you know any cool and smart people who would try that? Can this be proof enough now?
    Her haircut was cool, that’s about it.

  25. Size Does Matter says:

    I just don’t get it. Charlize Theron is one of the most beautiful women ever. She is successful and wealthy independently, so what does she get out of this? Why? Hopefully he is nice to her and she never joins the ranks of Halle Berry, Christie Brinkley, and Elizabeth Hurley – stunning, gorgeous women famously wronged by douchebags.

  26. Lark says:

    Ugh. Madonna filed a report with the police after Sean Penn beat her. With Charlize’s family history, why she wants to get with a known abuser is beyond me. It amazes me how “hushed up” that got.

    • She didn’t though–that’s why it’s not common knowledge.

      • Original A says:

        Yeah, there’s a police record out there and it’s public. Maybe Madonna refused but the cops filed something, or maybe she dropped it but there is paper proof. I mean even the LA Times acknowledged he beat the shit out if her

    • Trashaddict says:

      Oddly enough, a lot of people who have been abused end up with abusers. Maybe it’s the protectiveness (translation, “ownership”) factor. You think this guy’s going to take care of you and rescue you from the crappy past you’ve had. Run, Charlize, do not walk, to the nearest exit.
      Weren’t there blinds about how bad he treated Robin Wright on CDAN?

  27. Ice Maiden says:

    Charlize has always seemed rather asexual to me. One of the most gorgeous women on earth, but somehow not very sexual. Does anyone else get the same impression?

    • tera says:

      Heck no. She seems the exact opposite. Very wild and fun, but kind of like a guy in a beautiful woman’s body.

  28. Cinderella says:

    Maybe they just partied together. One of those “extended” parties.

  29. tera says:

    I didn’t know you liked Charlize, Kaiser. I always thought you disliked her because she was so beautiful and talented and thus competition for your Angelina.

    Charlize is a tough chick. She will not put up with Sean Penn’s mess. Believe that. People can change. He went from punching photographers to sleeping in tents in Haiti. Charlize does a lot of philanthropy too and is very private. We don’t know these people. They could be a very sweet couple or maybe just friends with benefits. Charlize seems like the type that would be fine with that. Especially since she has a kid now.

    And she never dated Seth McFarlane. They did a movie together.

  30. junegorilla says:

    Her Dad was so violent that her Mother killed him in self defense right? Not exactly a roadmap to choosing great mates.

  31. Godwina says:

    Gah! Charlize and SETH M? Sean P not much better. I am ignoring all of the above and continuing to believe that Charsgaard is actually a thing. That is a much happier place for me.

  32. No Wonder... says:

    No wonder Charlize looks so cranky lately. She’s with Mr. Cranky.

  33. Anna-fo-Fanna says:

    I…how could you hit it with Sean Penn?!? He looks like a caricature of himself, like he’s constantly in Dick Tracy villain makeup!