Jay Cutler does not really care about anything. I think that is pretty obvious when you watch him play quarterback for the Bears. Too harsh? Let me know when he wins a Super Bowl. Anyway, considering how low maintenance Jay is, I'm actually shocked he is engaged to Kristin Cavallari. Pretty much the opposite of Jay. He does what he wants. When he wants. How he wants. When the couple got back together after Jay had stopped seeing other people which was happening a lot the first time they were together, Jay texted Kristin and said they should get engaged again. Kristin said ok so Jay sent the ring from when they had been engaged before to Kristin in the mail. Nice.