After only three months of dating, the teen dream of the nineties asked one of her backup dancers to marry her, but he turned her down, just so he could ask her instead.
She said yes, and they picked out a $40,000, 5-carat double-banded ring for a June 2004 engagement.
A Second Chance for Love
This singer joins the two-timer club on this list with a sparkler from actor and comedian Russel Brand, but get this – she didn't like his first choice!
The couple returned the original 5-carat Cartier ring he had picked out, swapping it for a round-cut diamond on a gold band she sported until they separated after a little more than a year of marriage.
If you haven't guessed by now, we're talking about the beautiful Katy Perry.
These celebrities really can't seem to make it work. Who will be the first celeb to make the three-peat? Read on to find out!
Yes, Britney Spears and first husband, dancer Kevin Federline, certainly have a unique engagement story to tell.
Their engagement was short, but at least it managed to be shorter than their marriage – they split in 2006.
Country Music Stars Know Good Design When They See It
This country music queen and her beau worked together to design her ring, and they came up with an $85,000, 5-carat oval diamond set in rose gold fleur de lis.
It's a piece with an antique feel that also espouses modern design and sensibilities.