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WATCH: Sara Sampaio Is One Of 10 New Victoria's Secret Angels! If Harry is indeed dating Sara, could there be some awkward Taylor run-ins in the future?Taylor is famously besties with VS models Karlie Kloss, Lily Aldridge and Martha Hunt, though according to , Karlie is stepping down from her Angel duties soon.On a rainy night, the pair was seen together enjoying a cozy dinner date at Craig's, a popular restaurant (also, one of Jenner's favorite eateries) located in West Hollywood.When their dinner date was over, the teenagers drove off together through a back exit.Check out the complete timeline of the couple's dating relationship below! 20, 2013 -- Taylor Swift's former boyfriend spotted with Kardashian clan member: the couple's first official date One Direction was in the U. to promote their most recent album, Midnight Memories.The frontman of the band Harry Styles had reportedly met the American reality star Kendall Jenner at CBS studios in Los Angeles, where 1D was recording a performance for X Factor.Harry Styles made an appearance on The Jonathan Ross Show, and when the host asked him about what he was looking for in a girlfriend, he replied: "I think you know when you find someone, I guess. 21, 2013 -- Morning after the first dinner date: Harry Styles meets the parents, bonds with Bruce Jenner at his beach house in Malibu "Harry, Niall, and Bruce went golfing," a source claimed. It worked -- Bruce loved Harry." The British boybander won over the protective father's heart by talking about Bruce Jenner's favorite pastime.Sources tell ET that model Sara Sampaio spent the night at the 21-year-old One Direction star's New York City hotel on Friday night.


The 19-year-old singer was driving a black Range Rover, while the 18-year-old reality starlet kept closely to her phone, sitting next to him on the passenger seat.

Shortly after, Jenner made the date official by following Styles on Instagram.


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