Rumors about a Styles-Jenner love connection first swirled in 2013 but picked up again in late 2015 when the stars were spotted vacationing together in the Caribbean before New Year's Day. Neither party officially confirmed the relationship, but they were outed by Jenner's big sister Khloe on her short-lived talk show. "Do I think they’re dating? Yes," she admitted on Kocktails with Khloé. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating."