Jay Cutler and Kristin Cavallari engaged again and expecting × Close Staff reports Updated: January 23, 2012 at 12:00 am • Published: January 23, 2012 email print Google Survey FAQ Actress Kristin Cavallari, 25, and Jay Cutler, 28, Chicago Bears quarterback, broke off their engagement last summer but got back together in November. Now they're engaged again and expecting a baby. They told PEOPLE, "We are thrilled to announce we are expecting our first child together. It's an amazing time in our life and we can't wait to meet the new addition to our growing family." Cavallari was on "Dancing with the Stars" and "The Hills."