Sean Penn Gossip

Sean Penn gossip, latest news, photos, and video.

Charlize & Sean's Oscar weekend

February 28, 2014 18:10:12 Posted at February 28, 2014 18:10:12
Lainey Posted by Lainey
Photos:
Dimitrios Kambouris/ Frank Micelotta/ Getty

I can't. I still can't process this. All of the following: Charlize Theron and Sean Penn are together. Charlize Theron and Sean Penn are even posing together. What in the actual f-ck?! They were out last night at a party celebrating Pharrell Williams and his hat. They were just on holiday last week holding hands, like super romance. Full Story

Sean Penn’s Valentine

February 12, 2014 15:05:57 Posted at February 12, 2014 15:05:57
Lainey Posted by Lainey
Photos:
AdMedia/ Splash

Someone asked me the other day if we do anything special for Valentine’s Day here at LaineyGossip.com. I can’t remember. Am I nicer? This year I’m spending Valentine’s Day at home in Vancouver. With Miley Cyrus and not my husband. What’s the problem? Sean Penn will be spending Valentine’s Day with Charlize Theron, their first Valentine’s Day together as a couple. Full Story

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At the nail bar and kisses in the car

February 10, 2014 21:34:47 Posted at February 10, 2014 21:34:47
Lainey Posted by Lainey
Photos:
FameFlynet, AKM-GSI/ Splash

Charlize Theron went to the nail bar the other day. And Sean Penn went with her. Like, he didn’t pull up at the curb and wait for her to get in. No. He was inside. He accompanied her. And didn’t punch someone in the process.  A couple of days later, while driving around, they stopped to kiss at a red light. Full Story

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More Sean Penn smiles

January 28, 2014 17:40:32 Posted at January 28, 2014 17:40:32
Lainey Posted by Lainey
Photos:
Splash, Kevin Winter/ Getty

Can we just revisit those pictures from yesterday of Sean Penn and Charlize Theron holding hands, smiling, and (almost skipping)? Let’s do it for Jacek because I made him pay extra for them and he’s really cheap. Last night Sean spoke at the Grammys Beatles salute. Have you ever seen that clip of Sean Penn presenting at the Oscars the year Chris Rock hosted? Rock made a crack about Jude. Full Story

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Holding hands and skipping

January 27, 2014 18:00:54 Posted at January 27, 2014 18:00:54
Lainey Posted by Lainey
Photos:
Splash

That’s a sliggggght exaggeration, the skipping part, but look at them. Almost, right? Charlize Theron and Sean Penn are holding hands and (almost) skipping. Laura suggested “walking jauntily”. The point is, these are two ordinarily crusty ass celebrities. And this is about as far from crusty ass as it gets: walking jauntily, holding hands…AND SMILING TOO?!? I thought they said in science class that two negative charges are supposed to repel each other. Full Story

Family time with Charlize & Sean

January 23, 2014 16:48:22 Posted at January 23, 2014 16:48:22
Lainey Posted by Lainey
Photos:
FameFlynet, INF

Can we play Photo Assumption with this shot of Sean Penn and Charlize Theron’s son Jackson at the grocery store this week? I wish we could get a look at the boy’s face. But his shoulders, to me, are side-eyeing the sh-t out of his mom’s boyfriend. This is why Photo Assumption isn’t an exact science. Full Story

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Charlize: Sean’s co-host?

January 13, 2014 20:38:48 Posted at January 13, 2014 20:38:48
Lainey Posted by Lainey
Photos:
Joe Scarnici/ Kevin Mazur/ Getty

Sean Penn hosted a fundraiser for Haiti on Saturday night, major stars in attendance, including Charlize Theron, his…girlfriend? Can we call her his girlfriend now? There were photographers all over the place. And she sat next to him, and they were ok with the pictures, and it was almost like they were co-hosts, partners. Full Story

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A movie but not dinner

January 7, 2014 22:13:18 Posted at January 7, 2014 22:13:18
Lainey Posted by Lainey
Photos:
VLNY / VLUV/ Splash, Keystone

Charlize Theron and Sean Penn. They've seen each other every day this year. Last night they went to the movies. Not sure what they saw. But God I'd love to sit behind those two, both Oscar winners (and I think in the same year too) looking up at Leonardo DiCaprio on the screen. Wouldn't you want to hear their thoughts? Anyway, a trip to Hawaii, NYE, sleepovers at home, then a movie date -- has this changed your assessment as to whether or not it's a casual hookup or a relationship? Wait. Full Story

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Charlize & Sean: Sunsets & Sleepovers

January 3, 2014 17:25:59 Posted at January 3, 2014 17:25:59
Lainey Posted by Lainey
Photos:
Dmac /Goodwin /FAMEFLYNET PICTURES, Sharky /Splash News

I posted about Charlize Theron and Sean Penn spending New Year’s together in Hawaii the other day – click here for a refresher. They’ve known each other for years. There was reason to hope that it was a friends-only holiday. But now even PEOPLE Full Story

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Charlize’s NYE with Sean Penn

December 31, 2013 15:56:33 Posted at December 31, 2013 15:56:33
Lainey Posted by Lainey
Photos:
AKM-GSI / Splash News

Check out Charlize Theron on the beach in Hawaii. I had no idea her hair was so curly. Did you? Some believe that Charlize is staying with Sean Penn while on holiday. He has a beach house there. But there’s been no suggestion that the two are dealing with each other romantically. Apparently it’s a friends-only situation because the two have known each other for years. Full Story

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Exit Brahim, re-enter Sean?

December 11, 2013 18:32:25 Posted at December 11, 2013 18:32:25
Lainey Posted by Lainey
Photos:
Dimitrios Kambouris/ Getty

Madonna’s publicist has confirmed to Gossip Cop that she and Brahim Zaibat, now 25, are over. They’ve not spent a lot of time together in the last few months. And she’s been spending more and more time with Sean Penn, most recently in Haiti when she joined him with her children for fundraising efforts. Full Story

Sean & Rocco

November 27, 2013 17:04:55 Posted at November 27, 2013 17:04:55
Lainey Posted by Lainey

Madonna is in Haiti with Sean Penn to support his J/P Haiti Relief efforts. There are, so far, no official photos from the trip but … Rocco Ritchie, 13, is on Instagram. And he posted a shot of him with his mother visiting a hospital. Full Story