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To Kim's credit, she didn't marry either of them, which shows a huge amount of self-restraint (for her).
It was the early 2000s and tween heartthrob Aaron Carter was all about the fresh-faced Disney girls. ), a teenage love triangle was born (think Brad/Angelina/Jen, with more acne and hormones).
Once the afternoon was over Riri changed her get-up to a skin-tight leather mini dress and matching coat for an evening at Jay Z's concert in Inglewood.
She was clearly having a great time singing along to his hits and was even seen posted up with an alien...
Aaron eventually went back to Hilary, only to cheat on her again.
Fast-forward to today, and Hilary is a happy mom to Luca and Lindsay and Aaron … Besides Justin Timberlake, Britney Spears seems to favor "regular" dudes over fellow celebrities (KFed was her backup dancer, while ex-fiancé Jason Trawick is a talent manager, and her ex-boyfriend Charlie Ebersol is a TV producer) — I'm guessing they are less high-maintenance.
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Some couples just fit — Bey and Jay, Heidi and Spencer. But more often than not, celebrity relationships are more flash-in-the-pan than built-to-last.
She went on to date John Mayer, Jake Gyllenhaal, and Harry Styles, and he … Both parties have since admitted that this was literally just one date but we can't help but wonder what might have happened if sparks flew …