Amber Heard was apparently on a date with Sean Penn at the Sunset Tower Hotel

Amber Heard keeps it stylish at annual WME Talent party

Does Amber Heard have a bad picker? That’s what I wonder. Bad picker or not, she has some really bad luck with men in particular – I think her picker is probably fine with women. But men? Her male lovers are a big pile of YIKES. There was the abusive bag of dirty scarves, there was the billionaire who possibly is into sex parties, and then there’s this… Amber Heard was seen out on a date with Sean Penn. Oh, girl… NO.

Elon Musk’s ex Amber Heard clearly has a thing for bad boys — the actress has just shared a romantic dinner with Sean Penn. Amid showing up at a series of Oscar parties — also attended by billionaire Musk — in Hollywood last weekend, sources exclusively confirmed to Page Six that Johnny Depp’s ex-wife Heard also enjoyed a late-night date with Penn.

The famous pair was spotted sharing dinner at A-list haunt the Tower Bar at the Sunset Tower Hotel over Oscar weekend, “Page Six TV” first revealed. A fellow diner told us, “Amber Heard and Sean Penn looked like they were on a date. They shared a bottle of red wine and were flirty and intimate with each other, at times in deep conversation and at times laughing.”

Reps for both Heard and Penn didn’t comment.

The source added that Heard and Penn’s date happened after Heard had graced top Hollywood agency WME’s Oscars party, which was also attended by Musk, who mingled separately from the actress with stars including Leo DiCaprio and Tobey Maguire. Heard was seen leaving the starry WME party alone shortly afterward.

The insider added, “Amber showed up in the same dress she wore to the WME party for her date with Sean. She looked beautiful and seemed happy, even if she may have avoided a run-in with Elon earlier in the night.”

Heard and Tesla billionaire Musk — who we first revealed were dating in 2016 — just split for the second time. They first broke up this past August, and the tech titan told Rolling Stone, “Well, she broke up with me more than I broke up with her, I think,” he explained. “I was really in love, and it hurt bad.” They reunited in December only to split again in February.

[From Page Six]

So is it a bad picker? Or is Amber working some kind of angle? Considering the way Page Six is framing this with all of the references to Elon Musk, it feels sort of like she’s working some kind of angle, like she’s trying to make Elon jealous by making sure he knows that she was out on a date with Sean Penn. That’s what I’m going to choose to believe until further notice, because I just can’t believe that Amber Heard would willingly go on a date with an angry ham hock for any reason other than “she’s trying to make someone else jealous.” As for Penn’s side of things… I mean, I understand WHY he would think that Amber is into him, just as I understand why he’s into her. She’s young and beautiful and she reads Ayn Rand or whatever. They probably talked about Noam Chomsky and tried to sound intellectual.

Sean Penn looks dapper arriving to LAX

Photos courtesy of WENN, Backgrid.

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109 Responses to “Amber Heard was apparently on a date with Sean Penn at the Sunset Tower Hotel”

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  1. fruitloops says:

    What man would be jealous of Sean Penn? And Elon Musk, of all people.

  2. Patricia says:

    Oh my god you’re right, I bet they try so freaking hard to sound intellectual. Hahaha. Well, I hope she isn’t starting up with old ham face. But perhaps she’s sadly a drama addict or a woman who only knows abuse. I don’t know about her upbringing, but I know women from abusive childhoods who end up with an abuser over and over. I hope she’s not one of them. She’s been through too much already.

    • Lilith says:

      I hope she get it right with her love life. I feel sorry for her for some reason. She seems vulnerable.

      • cathy says:

        I think she likes to act like she’s very independent and strong but has insecurities just like all of us. I got the feeling she was really into Musk but their lives didn’t fit together. He’s busy changing the world and I think she’s just into partying and having a good time right now. She also appears to be very manipulative. It looks like that video of her kissing that guy in Australia was staged to get at Musk so I wouldn’t be surprised if this wasn’t staged too.

    • Elizabeth says:

      So much this. I was abused by my mother and I’m now leaving a decade long emotionally and physically abusive relationship. I’m am so scared to go through this again that I don’t see myself ever having another relationship.

      • Patricia says:

        Elizabeth sending you congratulations for ending that relationship. It’s very very very hard.
        I was also severely emotionally abused by my borderline personality mother, and I was in an emotionally abusive relationship for seven years and I felt like I would die when I left. I did a lot of therapy and have now been happily married for five years to a partner who treats me beautifully. There’s always hope. Therapy can help so much. I wish you the best and a future with a wonderful partner when you are ready for that. I still internally deal with the abuse my mother gave me (I know we always will, as abused daughters) but I no longer replicate it in my relationship.

      • Teebee says:

        Wishing you success as you disentangle yourself and heal. You sound like you’ve done a lot of soul search8ng and self realization. Hope you’re surrounded by love and support as well! Peace!❤️

  3. Ally says:

    To quote a line from Frasier, “On what desert island with no hope of rescue was this?”

    Seriously, bottom of the barrel, Ms. Heard.

    Inexplicable that the angry ham hock, as you perfectly put it, can score dates with all these sentient women (Johannsen, Theron).

  4. Kitty says:

    Bad choice of men if you are trying to avoid abusive situations. Wasn’t she arrested for abusing her ex girlfriend before?

  5. manta says:

    Weird. I would think that making the exes jealous would be more his thing. Just a few days ago Robin Wright was pictured in Paris with her new man, both wearing rings on that finger.
    Enough to tick Penn.
    And Theron is in full promo mode.
    He has to stick it to them (or so he thinks)

    • magnoliarose says:

      Because they dumped his nasty self so I can believe it makes him angry. Especially Theron since he claimed she was the love of his life and she ghosted him.

    • Jayna says:

      Why? He and Robin are back friendly now. They’ve been seen together several times. He has been dating a very young actress for quite a while, the daughter of somebody famous. If he’s out with Amber, maybe they are over. I don’t know. I don’t think he’s focused on exes.

      • Boxy Lady says:

        @Jayna Leila George, Vincent D’Onofrio’s daughter with Greta Scacchi. From Leila’s side, that might have been one of those “daddy issues” relationships. (I had a couple of those when I was young.) It has been said that Vincent wasn’t really around for Leila when she was young and Vincent and Sean are nearly the same age. Hopefully that’s over; I don’t think Sean is a great choice for anyone, really. 😝

  6. Other Renee says:

    Lady needs a new picker.

  7. MRsBump says:

    Damn, i used to feel sorry for Amber, but going from Johnny Depp to Sean Penn?? Seriously? This is a tragic case of “out of the frying pan, into the fire”.
    How can she not know about his past as an abuser, even I know, and I’ve grown up on a remote island in the middle of nowhere !
    I’ve got no more sympathy left. Choosing an abuser once is a mistake, twice is a life choice.

  8. Rumi says:

    I don’t get why she picks these guys. If your going to go for someone older at least go with someone that isn’t all about the ego.

  9. AnnaKist says:

    “They probably talked about Noam Chomsky and tried to sound intellectual.” I love t!

    Bad picker or angle, either way, it’s not good.

  10. Sarah Anne says:

    There’s no way this could end badly.

  11. Q T Hush says:

    Why would she even be attracted to Sean? He’s a known temperamental brat which hasn’t improved with his age. GET OUT NOW!!!

  12. mannori says:

    Interesting pairing, l wonder why would he go on a date to the Sunset Tower Bar, one of THE places to be seen with in LA with an attention seeker in a night gown hanging on his arm….let me think. Oh right! His ex. Robin Wright was seen with her new French hubby wearing wedding bands on Tuesday.

    every time Robin gets engaged or is seen with a new man he feels the need to upstage her with a new high profile girlfriend and a pap op or a PR planted article. He did exactly the same when Robin got engaged to the scientologist guy: few days after he arranged a photo op with Charlize in his Hawaiian home, which is in a private gated beach.

    • Enough Already says:

      This is an unfair presumption and part of the golddigger garbage the Depp defenders always trot out. The circles she runs in hardly makes it likely that she’s going to date the greeter at Wal-Mart. And it’s none of our business. When men stop marrying beautiful women they don’t “deserve” to be seen with I will judge women for dating financially secure men.

      • mannori says:

        Nowhere in what I wrote *here* mentions what you are saying. But the funny thing is that i totally agree with you and specially with this:
        “When men stop marrying beautiful women they don’t “deserve” to be seen with I will judge women for dating financially secure men.” On other post right above (that it was deleted I don’t know why) I wrote that gold diggers are a way for the universe of making some justice to horrible men. I don’t really judge her for that. She’s not trying to fleece honest decent guys. I’m fine with that.
        I don’t like the treatment people gave her on the Depp debacle. And I know gold digger is an offensive an misogynist label. But I don’t think she’s all this innocent angel looking for love. I think both her and Penn are using each other, for very different reasons.

      • Bettyrose says:

        I agree with both of you, and I would never use the term golddigger, but there’s a psychological issue with a woman seeking the social validiation/protection of an older (read more powerful) man. This is clearly not a case of her repeatedly falling in love with older men.

    • Jayna says:

      Sean has been seen with his much younger girlfriend lots of times over the past year or so. He and Robin are back friendly, seen together several times, once having lunch with their daughter’s boyfriend, where Robin and Sean seemed upset with the boyfriend about something, another time taking a flight together to some event for one of their kids. I think they are long past worrying about each other as far as who they are dating..

      • mannori says:

        I respectfully disagree. The fact that they hang out together for their kids doesn’t mean that they, or more precisely him is well past her. Neither the fact that he’s dated other women. I believe that even after 10 years they divorced he still holds a grudge against her. He’s been petty and whiny about her for years after the divorce in interviews and even while he was with Charlize. As recent as last year he was doing a movie just out of revenge and to get back at Robin (a movie that it was her pet project for years and he ended putting Charlize in Robin’s role). In the news reporting her marriage to her French guy he gets to be the ex, the footnote and you can bet he hates that. He needed to upstage that.

    • maitai says:

      His whole thing with Charlize was not only the most out-of-character thing for her, but also the most hypocritical thing for him.
      Charlize never does any of that staged pap photo bullsh*t for herself. She’s well known for hating that sort of thing. And Sean claims to loathe the press and paps, but he’s fine with roping his then-girlfriend into staged stuff? He’s pathetic.

      I’m so glad Charlize is far far away from him. He was actually starting to drain the fun out of her. And Robin Wright can attest to life being much better without him around too.

  13. hkk says:

    Is she desperately trying to bag an uber rich guy or what? Sorry but that is the only thing that comes to mind. Depp, Musk and Penn eeeeeekkkkk

  14. Lindy says:

    Oh girl… Your picker is way off. I get it, mine was, too. It took a long time (and a good therapist) for me to realize why I kept going for guys who were so terrible. I honestly just feel for her. This is such a bad idea.

  15. Max says:

    This is like her 3rd boyfriend in a row who is much older,richer and more famous.If she really dates him even though his temper and anger issues are known then it’s shady af.And Sean Penn will probably make Depp look like an angel eventually.

  16. Eric says:

    I guess Amber is moving on to the leathery look. Sean looks like the last man on earth, stuck on a desert island, weathered by the elements and shaving with a sandpaper razor.
    Bleak!

  17. Yawn says:

    Pictures or it didn’t happen… I want to believe this girl isn’t a complete and total idiot by going out with the known ham hock abuser… lol…

  18. CKY says:

    I think her picker is bad. There’s good things about Sean penn, obviously, but the good outweigh the bad.

  19. Reef says:

    When I found out she’s an Ayn Rand fan, everything about her makes sense.

    • Bebe says:

      Well I was confused about why this article mentioned rand and Chomsky in the same breath. It’s not like rand believed in socialism or economic equality… She was anti socialism even social democracy and altruism.. Chomsky on the other hand is a socialist.
      If heard is a rand fan she’s a conservative in terms of the economy most rand fans I know are republicans or often libertarians, economically conservative but socially liberal.

    • Lindy says:

      I didn’t realize that. Ugh. No wonder she and Musk didn’t last. He’s like the tech anti-Rand (unlike so many of the libertarian tech bros).

  20. Sarah says:

    She looks terribly unhealthy in that top pic- like, Lindsay Lohan circa 2009 skinny.

  21. A says:

    I assume she had abuse in her childhood, based on her choice of Depp and now Penn. Abusers and those who have suffered abuse seem to pick up on some kind of energy that attracts them to one another, even before the abuser displays any problematic behaviour. In this case, since Penn has a history of abuse, it should really be a red flag for her to question any attraction and stay away.

  22. smee says:

    I wish there was a better pic of this dress she dared to wear TWICE because I think its made of woven silk ribbon and it’s incredible. She looks very thin.

    Bad picker fer sher. Seems like she’s trying exclusively for only super well-known successful type and not giving a crap about their character…?

  23. serena says:

    Omg just what is wrong with her? Why does she keep dating the douchest douches?

  24. minx says:

    Angry ham hock, I’m dying.

  25. Fed Up says:

    I wouldn’t call it bad luck. More like bad choices and taste in men.

  26. Bebe says:

    I don’t know why people act surprised it’s pretty obvious she likes rich powerful older men. That’s her type. Penn fits perfectly in this regard. Depp, Elon and penn are all cut from the same cloth, talented, problematic and ultimately they all have far more power, wealth ( and talent) than she has.

  27. Jussie says:

    As far as that ‘sex party’ goes, many attendees, mostly female execs and entrepreneurs, denied that it was anything of the sort.

    The only actual claim made was that there was a big seating area where a few couples were making out, and that there was an attendee walking around offering people MDMA. If that’s a sex party then every big party is a sex party.

    • Susie says:

      Well lainey did imply in a blind a few months/weeks back right before or after they broke up that musk has sex parties that all the uber rich and celebrities want to go to the most. So there might be something more than what page six has there.

      • isabelle says:

        I live in a “rich” town and my first two weeks here I was invited to one of these parties. They simply asked me to attend their small party where singles would be and some couples. Really didn’t think anything about it. Another girl living here warned me and other people did as well. No it wasn’t Musk but for another uber wealthy person. These parties are a thing in these rich elite circles

      • Jussie says:

        Lainey’s blind was that Heard and pretty much her whole friendship group were very much into those parties, so it wasn’t just Musk’s thing. He definitely never held parties like that with his ex-wife.

        A private, exclusive sex party with primarily close friends and various powerful/famous people has very different implications from a large work/networking party turned orgy. If anyone really thinks people like Musk and Sergey Brin would attend a sex party filled with strangers and not at the very least have everyone sign NDA’s they’re crazy.

      • isabelle says:

        @jussie, don’t be that naive, rich men can do anything they want and get away with it, more things than you couldn’t even imagine.

      • Jussie says:

        They can get away with it because they can do things like have everyone sign NDA’s before they enter a room, or pay people or media outlets off.

        In this case the ‘sex party’ was pretty much immediately written about in a major book, then the story was picked up by literally 1000’s of media outlets.

    • Eden75 says:

      If it was a sex party and everyone is consenting adults, who cares? If people had to sign NDA’s because there were people there who don’t want stuff like that public, who cares? Don’t want to sign or participate, leave. Not sure what the big deal is.

      And these are definitely not only for the rich and famous. They happen in a lot of places all of the time.

  28. Gurlplease! says:

    Good god! Couldn’t someone inform her that she could also date good men? There’s no rule forbidding you to date good men Amber, but you keep looking for these older douches

  29. Wurstfingers says:

    Uh… Her taste in men is horrible. So… Just stick to the Ladies, maybe?

  30. isabelle says:

    She has horrible tase in men and in the long-run it is exactly what will ruin her so called Hollywood career. girl…you need some serious counseling and psych help. There is something very off about her picking such awful abusive men, beginning to think she has a PD (seriously some PDs purposely pick abusers that mimic their behavior) or she needs very serious help.

  31. Ozogirl says:

    Going from one douche to the next… not a good idea.

  32. CrazyCatLady says:

    This guy married Madonna. Robin Wright, He was with Charlize Theron and Scarlett Johansson (I have a major girl crush on CT).

    He must be very charming at first. Just sayin.

    • Jussie says:

      You can kind of see that in a lot of his films. He can certainly act very gentle and sweet.

      I don’t know how anyone could see past the glowing fake tan and the obvious steroid abuse now though. That’s got to undercut any attempts to seem like a nice, regular guy.

    • maitai says:

      And now he’s dating 25 year old Leila George. Le sigh.

      But I think you’re right. I get the impression that he’s great at coming across as extremely charming initially. I think Robin Wright and Charlize Theron would probably have been drawn in by his humanitarian work too, since they’re both very empathetic women with their own charities.
      But whatever charm he works on these women it never seems to last very long. And worse, he keeps dating younger and younger.

      I still have no idea what he could have done to make Theron ghost him, but it must have been bad. She doesn’t seem like the kind of person to run away from something like that over dealing with it head on. And they are clearly not even friends anymore.

  33. Shappalled says:

    Elon Musk reminds me of a villain in a James Bond film.

  34. Pandy says:

    Geez go back to girls Your picker is off!

  35. Adele Dazeem says:

    Serious question: is she in some kind of financial trouble? I wonder what her finances are like.

    And why doesn’t she even go out with a millennial (or hell, gen x lol) person???

    • Jussie says:

      When she filed for divorce and was initially asking for alimony, her filings stated that her outgoings had far exceeded her income throughout their marriage. Which was pretty crazy since Depp was the one (over)paying for their houses, staff, travel, cars, the art, the expensive wine and so on. So she was spending more than she earned on incidentals basically.

      She pretty much moved in with Musk ASAP, then went to Australia where the studio payed for her accomodation. Now that she has to pay for her own home it wouldn’t surprise me if she’s having money problems. Maybe not right now, Aquaman would have paid ok, but she’s only got a couple of very small films on the horizon that won’t pay well at all. If she hasn’t cut back her spending massively she’ll definitely have problems pretty soon.

  36. kacy says:

    I think they are both trying to make other people jealous. Others have mentioned Robin Wright’s recent marriage. Elon just posted photos of him on the WestWorld set. Who’s on that show? Oh his favorite ex-wife, Talulah Riley…

  37. The Other Katherine says:

    GIRL. What are you DOING. I can’t even. *head explodes*

    Sean Penn. Good god. WHY?

    • KLO says:

      It is really amazing how a woman as beautiful as successful as Amber can not find a nice man her own age to save her life.

      Maybe she does not want to?

      Some above comment said she is addicted to “powerful” men. Maybe she is convinced that she has no power of her own (because of her past experiences, i dunno) and tries to make up for it by hanging on to these abusive, “powerful” dudes?

      Or maybe it is just the case of having to do all the wrong things before you are convinced that it is right to do the right, healthy thing?

      I wish you luck Amber. Stay safe.

      The only thing I am getting from this right now is that her relationship with her father must have been pretty fucked up. Some kind of unhealthy enmeshment or parentification going on.

  38. Racer1 says:

    Anyone have the receipts on her donating her divorce settlement to charity?

  39. LittlefishMom says:

    I hope they’re right saying she’s doing it to make that guy jealous because if not she should get Everlast tattooed down the side of her body.

  40. Big D says:

    Why bother going through the trouble of making him jealous by being seen with SP when she was the one who apparently broke up with ET- according to him?
    Doesn’t make sense to me.

  41. Anna says:

    She has a bad picker for sure, but anyone who picks her IS CRAZY.