The uber-famous duo were reportedly seen dining at the Tower Bar at the Sunset Tower hotel in Los Angeles during the weekend of the 2018 Oscars.
A diner at the hot spot told Page Six that "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 actors declined to comment to Page Six at the time of this story.
Insiders told Page Six that the date went down after Amber stopped by a top Hollywood Oscar soirée for William Morris Agency, which her ex, Ellon Musk, also attended. While he socialized with Leonardo DiCaprio and Tobey Maguire, the actress was spotted leaving the party by herself.
The Page Six source added that "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."
Amber and the Tesla billionaire, who dated in 2016, just split for the second time earlier this year.
"Well, she broke up with me more than I broke up with her, I think," Elon told Rolling Stone following their first breakup in late 2017. "I was really in love, and it hurt bad."
The two reunited back in December only to split again just last month, yet the pair can't seem to avoid each other.
The "Justice League" actress and the tech entrepreneur almost ran into one another again on Sunday, March 4, at a party at the famed Chateau Marmont in West Hollywood.