Real life Pip Boy
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I remember using something like this - they can hook up to a barcode scanner you wear on your finger
I have the same problem with my watch. I could tighten it but then it starts to hurt. Anyways I keep it just loose enough to be comfortable but tight enough I can correct it every half hour.
How much does your watch weigh?
Some are pretty heavy. Men's watches especially can be pretty hefty, easily 5oz.