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For me personally it was a 36mm DateJust with Roulette Date. The roulette date was my primary reason for purchasing. I just love the novelty of it, but I don't think it has the thousands of dollars worth of novelty that I originally thought it had.
However, my most disappointing Rolex to ever try on was the Daytona. I still think its a great watch, and I would love to add one to my collection. But even after trying on the White Face, Black Dial grail that so many are dying to get their hands on, the *feel* wasn't near what I had hoped for after all the hype. It was a gift for my dad from my grandmother for his Bday, and we ultimately ended up walking out with a RG/Matte Black YM on Rubber.
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