“Harry has always been ‘that guy’ for Kendall,” an insider tells PEOPLE exclusively. “She would love to be in a real relationship with him, but he’s always had issues settling down in the past with her because he has that rock star mentality.”
Styles, 22, and Jenner, 20, were first linked in January 2014, and reignited rumors nearly two years later after vacationing together in Anguilla in December 2015. Although Jenner’s sister Khloé Kardashian said the pair were “dating” at the time, they weren’t spotted again together until April of this year, when they went shopping in Los Angeles.
Following the pair’s dinner date last week at L.A.’s Tsabel, the source says the couple is “giving it another try, and she’s hopeful things will be different this time around.”
“Even though she’s dated and hooked up with other guys, she could never really get serious with someone because she never got over her feelings for Harry,” the source explains.
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In early April, Jenner connected with NBA star Jordan Clarkson and just last month, the 20-year-old was spotted out with rapper Tyler, the Creator, but a source told PEOPLE at the time that the pair are just friends. She’s also spent time out and about with A$AP Rocky.
Now, another insider told PEOPLE, Jenner is focused on Styles.
“Kendall’s so excited and happy about it,” the source previously said. “She’s always cared about Harry.”