Why I Can’t Date Sean Penn



Ok. Let me just state the obvious. Sean Penn and I will never cross paths and thus this post is all to make a larger point about the universe.  Furthermore, I will state the second obvious fact.  Sean Penn would probably have no interest in me and thus there is no need for me to state why I would never date him. Alas, I will still move forward with this hypothetical. Let me go back to one previous point. Sean Penn will never date me in part due to the fact that I am not a blonde. He has married Madonna-the queen of the Blond Ambition Tour.   He was married to Robin Wright -the Princess Bride. He was engaged to Charlize Theron the blond South African. and briefly dated Jewel.  I am all brunette -even when I dye my hair purple or red.

Let me start by noting he has done great humanitarian work, especially  in New Orleans-my favorite US city (after New York, of course) and that is a grand thing.  He puts his money where his mouth is (i.e. helping out in Haiti) and one can applaud that. I also loved his work in  Fast Times at Ridgemont High, as a surfer-stoner who popularized the word “dude” in popular culture. I say “dude” all the time; even before I moved to California.  He is an activist, I can get behind that as I am one myself. However, he reminds me a bit too much of what I have often seen in the non-profit field: the leader becomes the story both for the world and him or herself.


Recently, Sean Penn was in the news because he made news. He went and got an interview with El Chapo, the world-renowned drug cartel leader that escaped from a maximum security Mexican prison.  Sean Penn was able to do what others were not. Kudos to him on getting that “hard-to-get” interview.  However, such a get makes him even more insufferably egotistical.  At one point in the Rolling Stones article, Penn writes “Wasn’t it soullessness that I must perceive in him for myself to be perceived here as other than a Pollyanna? ” Can anyone tell me what that means? It reminds me of a time (well actually many times) where I saw a non-profit leader give a speech so empty of meaning that he even clapped for himself at the end of it and afterwards asked anyone in earshot how well had he done.

He is ostensibly a great actor having won two Oscars and having starred in widely lauded films such as Mystic River, Carlito’s Way, Dead Man Walking and Milk.   Thing is I haven’t really cared for any of those films. I always feel like there is some grand lecture behind those films and that he smugly acts his way through them. It is as if he is scolding us collectively.  Sean Penn is the personification of sanctimony. At 5’8″ he exhibits a bit of the short-man complex. Again, I have seen leaders like this in the non-profit world. They do grand acts and feel they are far superior to others often giving unsolicited advice on everything from how to run a board meeting to how to set up your own personal bank account.

Sean Penn is quoted as once saying  “There’s a lot of mediocrity being celebrated, and a lot of wonderful stuff being ignored or discouraged.”  That is actually a sentiment I can get behind. These days mediocrity takes a daily selfie. Wait! Does that sentence even make sense? I must be channeling Penn.  But even when I think I can agree with Penn he goes on to say the following as well: “When you act in a film, you’re inevitably surrounded by people you didn’t choose, right down to the set painter. I like being able to pick the family I’m waking up to in the morning that’s going to make this group effort to tell a story that applies to what’s interesting to me at that stage in my life.” For a man that sympathizes with populists across Latin America, he sure sounds quite elitist. Sorry that you can’t pick the painter on the movie set where you go to act for a living (an obscene living).


Yeah, if we were to go out to a bar on a date it wouldn’t end well.  I don’t mind intense atmospheres.  I do mind uncontrollable egos. I have left jobs for that reason.  At least, we could share in a love of New Orleans and maybe use the word dude a few times before we flamed out.





8 replies »

  1. I seem to recall him being photographed a lot with Saddam Hussein in the weeks leading up to Operation Iraqi Freedom and with Hugo Chavez after the Venezuela government control of private industry, Definitely an attention whore, so much so you’d think he was a millennial rather than a Gen X’er.

    Liked by 1 person

      • His narcissism has also lead him to take on that pseudo-intellectual weirdo personae that a number of actors adopt during the declining years of their career. I believe Marlon Brando was the first, followed by the likes of Robert DeNiro, Eddie Murphy, and Jim Carey.



    Pollyannas are people who are biased toward optimism. He’s saying he feels required by his preconceptions to have a negative perception of El Chapo, or risk being perceived as naive.


  3. I tend to think that some of these people are actually kind of insecure. At least Sean P generally keeps his work and his opinions on the “low down” which makes it easier to overlook if I choose to. I understand that narcissistic behavior is sometimes a mask for insecurity. I wish that some candidates, “leaders,” etc. displayed their narcissism and insecurity in the same low tones as Mr. Penn.


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