Funnily enough, my most sentimental watch is one that I got recently. My parents bought me a Seiko SSK GMT when we were on vacation celebrating my graduation from college. It’s the watch that I wear almost every day and it reminds me of how hard I worked to graduate and that my parents support me in life.
I actually asked someone in a local IWC boutique the same question. Apparently if you wind it too far forward either you get one free “do-over” where they’ll send it back and reset it for you. The other option is waiting until the date that you wound it to comes around and then wearing it again