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.
Sean Penn looks dapper arriving to LAX Amber Heard keeps it stylish at annual WME Talent party Sean Penn outside of a hotel in New York The Art Of Elysium's 11th Annual Black Tie Artistic Experience - Arrivals