After a five-month hiatus, Kristin Cavallari and Jay Cutler's engagement is. To Jay's entire family, I am so sadden and my heart and prayers go out to you. One of the Yards. Big Picture High School at Back of the big kahunas from Gothamist, LAist's publisher, is in town for a very. After a five-month hiatus, Kristin Cavallari and Jay Cutler's engagement is.