On September 29, 54-year-old Brad attended Silverlake Conservatory of Music's Annual Benefit and Art Auction.
Red Hot Chili Peppers bassist Flea, Brad's friend and cofounder of the charity, introduced him to spiritual healer Sat Hari Khalsa.
According to Star, the two flirted all night.
"Brad and Sat Hari hardly stopped talking," an eye witness told the US publication.
"She was laughing at his jokes, and he was hanging on her every word. It was clear there was a connection between them."
"Though the room was full of guests, Brad only had eyes for her," adds the source. "It was like they were the only two people there."
After Brad's 2016 split from Angelina Jolie, Brad has done plenty of "soul searching", Star claims.
"These days Brad is in to crystals and getting in touch with his spiritual side. It doesn't hurt that she's kind, interesting and beautiful," a friend tells Star.
But, Brad's new found interest in Sat Hari has left Jen reeling.
"Jen was devastated when Brad and Angelina got together, and she doesn't want to go through that again," adds the insider.
"Even though Brad has changed, it seems like he hasn't totally put his womanising behind him, and Jen's not going to stand for that."
Brad Pitt and Jennifer Aniston and yet to respond to Star's report.