Wifey Of: Jay Cutler, Chicago Bears (NFL)
Occupation: TV Personality
The former star of Laguna Beach and The Hills has only made one turn as a WAG, but she is doing her best to make it count. Cavallari and Chicago Bears quarterback Jay Cutler began dating in the fall of 2010, and got engaged in April of 2011. Perhaps realizing he made a hasty choice, Cutler called off the engagement a couple months later. Upon deciding their haste was in fact a good decision, the pair got re-engaged four months after that. Two months later, they announced the Cavallari was pregnant.