5/12
Ke.Mazur/Jason Nevader/WireImage.com
Just as her career was taking off, Spears' two-year relationship with Reg, her first boyfriend, came to an end.
"It wasn't that I was changing," she explained to RS. "We broke up before any of my success had happened. He became insecure with himself, I felt. I wasn't gonna do anything—I'm a straight-up, honest person, and if I was gonna do something, I'd tell him before I'd do it and end the relationship. I was really head over heels in love. I don't think I'll ever love somebody like that again. I just woke up one day and click, it was gone."
As well all know, she would go onto love somebody like that again.