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I think putting your fiance's initials on it is a great idea. It's really awesome that the watch has made through that many generations to you. I read in Dear Abby once that pocket watches are a traditional wedding gift from the bride to the groom, they are supposed to help the groom get to the ceremony on time. I think it's the perfect gift, no need to get anything else except maybe a card to explain how special the watch is. Congratulations.
I think that your fiance will love it. Instead of having his name and the wedding date engraved on it though, I would enclose a card with it. The reason for the no engraving is because if you and him are planning a family some time in the future, it will be easier to pass down to the next generation without the engraving. Technically, this watch would be from your father to him, so if I were you, I would also get him something else.
I think this is a very special and sentimental gift. Perhaps if you want to pass it on to your kids (if you are having kids) something other to engrave? Maybe a special quote or something? Anyway, yes stick with this gift, I bet it will mean a lot to him!
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My engagement ring and wedding band are my fiance's maternal great-grandmother's so I wanted to give him something reflective of my family as well. My fiance had mentioned to me that he has always wanted a pocket watch to wear on special occassions with his tux or tails. My grandfather gifted my father two pocket watches and my father gave one to my brother and had another. I asked my father for the second one over Christmas and he was so excited to give it to me to give to my fiance! My grandfather passed away when I was 10 and I'm so sad that he never had the opportunity to meet my fiance. The pocket watch is so awesome. It is my grandfather's great-grandfather's and it has both my grandfather's initials on it and his great-grandfather's as well as a design he had etched over his great-great-grandfather's initials. I had to get a new chain but it is now in working condition.
Do you think I should add my fiance's initials to the watch too? Or our wedding date? What are your thoughts on this present? Do you think my fiance will like it or should I get something else too since this was gifted?