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A Rolex Submariner Date or a GMT Master II (your preference as to which) is the watch you will have for the rest of your life. Personally, I'm a die-hard Sub man. Simple, versatile, rugged as hell, still beautiful under a shirt cuff if dressing up, and more water resistance than I'll ever need. You will never want to trade either a Sub or a GMT for anything else. You will not have any nagging "what if" thoughts in your head about having gotten something a little less expensive.
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