So things appear to be going well with him and reality star Kristin Cavallari.
People is reporting that "He surprised her with a quick trip to Cabo to ask her to marry him."
Cavallari, 24, who also appeared on The Hills, and Cutler, 27, the quarterback for the Chicago Bears, have been dating since last fall.
And good for her, she became a success by doing nothing and Cutler has enough money to keep her doing nothing. Hooray!!!
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