Jenny and Will dated for quite some time before they got engaged on July 14th, 2014.
The two were on a romantic getaway in Newport, Rhode Island when the rehabbing third baseman Middlebrooks got down on one knee and popped the question with her family in attendance.
Prior to dating the CBS sideline reporter, Will was once engaged to former Dallas Cowboys cheerleader Ann Lux. The two met each other at the age of 12. The couple was scheduled to marry in December 2012, but they broke up in August of the same year.
Photo Credit: Will Middlebrooks