Really appreciate all the responses! I'm sure it'll all be fine even if they do have lots of questions, just helps to think about what I should be considering and bringing (proof-wise) ahead of time. 
)
One thing I realized is that 90% of the times when I cross, they ask me if I'm bringing anything that's staying in the country. I guess at that point I kind of have to list the ring along with anything else, and that'll get the conversation about proposing started, huh?
Oh yes, that is what I meant.canadianwoman said:Only bring this up if the border agent asks specifically.
Duty is something I hadn't thought about, and that could be interesting - the ring is a simple silver one that I made in a silversmithing class as a kid, so it's worth next to nothing and has no stones or anything, but I also don't have any kind of receipts. (And in case anyone was worried, yes, my girlfriend and I have discussed a few times using this for whenever I did propose, and she's fine with something that isn't gold and diamonds.viva-c said:You'll be in for a nightmare if you say you're proposing (plus they might try to charge you duty/taxes on the ring...) Just say you're visiting her, as usual.
One thing I realized is that 90% of the times when I cross, they ask me if I'm bringing anything that's staying in the country. I guess at that point I kind of have to list the ring along with anything else, and that'll get the conversation about proposing started, huh?