Yikes. Before there was Angelina, Jennifer, or even Gwyneth, Brad Pitt was actually dating some of Hollywood's youngest stars.

He did a lot of lesser-known things before becoming famous, but dating underage girls might be the cringiest. Fans have just noticed that his romantic track record from the '90s contains some relationships most people find troubling.

He Was 26 When He Dated Juliette Lewis, 16

In an IG post from a vintage pop culture themed account, fans are going off in the comments about how inappropriate it was for Brad to date someone 10 years younger than him when he was in his mid twenties.

While dating someone within ten years of his age range is usually NBD, Juliette Lewis wasn't really considered an adult at the time. The pair ended up dating from 1990 to 1993, when Juliette was 16-19 and Brad was 26-29.

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Brad met Juliette on the set of the TV movie 'Too Young To Die.' The film had Juliette playing a 15 year old exotic dancer (oof) and Brad playing her older "lover," according to the sketchy trailer you can watch here.

While Juliette had been emancipated from her parents and living independently from the young age of 14, fans still felt Brad shouldn't have been allowed to date her, chiming in on IG with comments like "Bradley what is this.." and "so gross."

He Was 24 When He Dated Shalane McCall, 15

Brad appeared on 'Dallas' in 1988, and got his first-ever onscreen kiss from the young actress Shalane McCall. She was only 15 at the time. Despite Brad being a grown 24 year old, the pair actually started a relationship while he was on the show.

"I met him an hour before shooting," Shalane told People in 1988 when asked how she felt about filming romantic scenes with Brad. "But it wasn’t awkward. We were laughing and kidding around."

People also reported that Shalane's mother had a different perspective on that experience: "I can tell you there was anxiety on Shalane’s part," her mom Cherie admitted. "It’s not cool at her age to admit how inexperienced you are. She’s only kissed about three boys in her life." That's probably quite different to Brad's kiss count by the time he and Shalane dated from 1988-1989.

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Now Age 56, He's Dating 27 Year Old Nicole Poturalski

She's less than half his age, and that's not even the strangest thing about Brad's newest relationship since divorcing Angelina.

Cosmopolitan reports that Brad met Nicole's husband (yes, husband) back in 2009 when he was filming 'Inglorious Basterds' in Germany, and took her on their first date to a Kanye West concert that same year.

No word on how her husband feels about her taking romantic trips abroad with this Hollywood A-lister, but their relationship is taking off nonetheless. All we can say is that Brad definitely has a type. See the resemblance to young Angelina?

NEXT: The Real Reason Angelina Jolie Is So Angry With Brad Pitt