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Jamie Lynn Spears, 16

Jamie Lynn Spears got engaged to boyfriend Casey Aldridge back in March 2008 at the young age of 16. Jamie and Casey welcomed their daughter, Maddie Aldridge, a few months later in June. The couple called off their engagement in March 2009. Jamie Lynn and Casey briefly reconciled in August 2010, but they have since gone their separate ways without walking down the aisle.

Image Source: Getty / Bruce Glikas
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