Reg Jones
In the mid-90s - before she shot to global fame with megahit '...Baby One More Time' - Britney dated football captain Reg Jones but the relationship fizzled out as her career took off.
He later reflected that it was "strange" to see just how famous Britney had become. Reg said: "We sat down on the porch at her mom and dad's house and talked it through. There were hugs and kisses and we agreed to stay friends. We are still good friends and I'd get back with Britney tomorrow if I could, but it is very unlikely we ever will."