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Of course, you want to look good for a date - you wouldn't go out and get a bad haircut to make sure she's not with you just for your looks would you?
Anyway, if she was only interested because of your watch I'm sure the relationship wouldn't last too long anyway. IMO those sort of relationships only work when it's what both parties are looking for, in which case a Rolex would be an essential part of getting ready anyway.
So on all counts, wear your Rolex.
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