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The Bachelorette

How Many Times Has Bachelorette Emily Maynard Been Engaged?

Emily Maynard is only 26 years old, but she’s already had three great loves of her life. The Bachelor alum and Season 8 Bachelorette has been engaged a total of three times, but, unfortunately, none of those engagements have ended in a walk down the aisle.

Emily’s first fiance, Ricky Hendrick, tragically perished in a plane accident in October 2004. Emily found out she was pregnant with her daughter Ricki days after the accident — and continues to live close to Ricky’s parents in Charlotte, who help raise Ricki.

During The Bachelor Season 16, Emily won Brad Womack’s heart (and final rose), but the two ended their engagement in May 2011. Then, surprising and delighting viewers, Emily agreed to be the Bachelorette for Season 8 of ABC’s romantic franchise. Emily fell hard for Utah entrepreneur Jef Holm, who moved to Charlotte to be with Em and Ricki, but the two ended their engagement in October 2012.

For now, Emily denies dating rumors, insisting she’s “good” staying single for awhile.

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