On a flight from Ireland to New York in June 2004, Britney Spears proposed to Kevin Federline, a backup dancer she’d been dating for about three months. “We were a couple hours into the flight and we’d been talking the whole time, stuff about life, wanting to have kids,” Spears told People magazine shortly afterward. “All of a sudden, I said, ‘What if you want to get married?’ ” She was 22 at the time, had sold 27 million albums, and had about $30 million, according to Rolling Stone. She had also been married before. Six months earlier, Spears had spent 55 hours wed to a childhood friend after making a 5:30 a.m. visit to a drive-thru chapel in Las Vegas. When Spears’s management team heard about her engagement to Federline, they set her up with a wedding planner, a jeweler—and Laura Wasser.
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