"I don't know what he was thinking!" Bill Decker, one of Pitt's Sigma Chi brothers at the University of Missouri, told RadarOnline.com.
Oklahoma-born Pitt, now 54, enrolled at the University of Missouri in 1982, majored in journalism and served as Sigma Chi's social chairman — largely through his skill with coeds, Decker explained.
"The girls gravitated towards him. I didn't really see it myself," Decker admitted. "But I can't grade men's looks. I was like, 'OK.'"
Shortly before he would have earned a degree, Pitt headed to Hollywood. He married Aniston in July 2000, and the two got divorced five years later, after he hooked up with Jolie on the set of Mr. & Mrs. Smith.
The A-listers are expected to finalize their bitter divorce in the next few weeks, sources have said.
Another old school chum of Pitt's, Mark Fauser, gave his buddy high marks for his handling of the messy breakup from Jolie.
"There is no book or guide in how to deal with the public scrutiny, the lack of privacy, gossip, the wackos, insults and stalkers," Fauser told Radar.
"I'm very proud of him," he added. "He is a true actor, a smart guy and has balanced himself well. Go Brad Pitt. Go Mizzou!"
Despite Fauser's enthusiasm, it remains to be determined what he and Pitt's other pals think of the star's new flame, MIT professor Neri Oxman.
We pay for juicy info! Do you have a story for RadarOnline.com? Email us at firstname.lastname@example.org, or call us at (866) ON-RADAR (667-2327) any time, day or night.