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She wants me to buy a Rolex... but I feel that's because she is being shallow about it being a Rolex.
Don't get a Rolex then. For what it's worth I don't think there's any point in buying an expensive watch that isn't the most comfortable thing to wear, especially if you plan on wearing it daily, you'll only end up resenting it.
Yes, these are questions I've asked. It'll be insured. I will not use any of them whilst exercising, so having a leather strap isn't an issue. The front runners at the moment are, I think, the Speedmaster and Tudor. I would consider buying both at some point. My girlfriend doesn't think either of them are special, but I don't care. She wants me to buy a Rolex... but I feel that's because she is being shallow about it being a Rolex. The Speedmaster and Tudor also fit under my sleeves the best. Think I'm talking myself into what I should buy here....