Congrats, OhCanada ... very exciting news for you!!
I agree that unexpected is good. When I think back on how I proposed to my wife, one of the things I am proudest of/happiest about is that not only she but almost *everyone* else among our families and friends was taken by surprise (except one suspicious friend who thought it odd that we would visit Nantucket in the dead of winter). So I would say that if you're at all able to keep a secret -- do it.
I'd definitely agree with what Lex said too ... try to pick a special/romantic/unusual setting. Our winter getaway made it extra-meaningful for us, and gives us a place we can always go back to relive that happy time in our lives. We bought this perfect poster while there: A painting of abstract "bride and groom" whales (sounds weird, but it's cute) with the words "Happiness Is Nantucket." It's now framed and hanging in our living room and brings back great memories.
Pay attention to as many little touches as you can. In my case, this included things like arranging for an extra-nice room with a fireplace and canopy bed, finding a really romantic place for dinner, and requesting in advance that champagne and flowers be delivered to the room. I let the innkeepers (but nobody else
) know in advance that an engagement was in the offing, and being familiar with the island, they gave me TONS of helpful little tips.
That said, don't try to script the actual proposal too carefully -- nothing ever goes exactly according to plan. In some ways, my proposal was a comedy of errors, but I rolled with the punches and now have an amusing story to tell people: It was a gusty, snowy evening on the deserted main street in Nantucket village, with holiday lights and festive storefronts all around us. We were walking back from dinner and I stopped to say I had another holiday gift (it was Dec. 26). I pulled out a wrapped box that ANY woman should've recognized by size and shape, but she didn't want to open it there because she was afraid the contents (a sapphire/diamond/platinum ring that I had selected on my own) would blow away. So we walked the several blocks back to our inn, with me dying of anxiety the whole way, walk in the room and find an ice bucket with the champagne I had requested earlier (assuming we'd be engaged
before returning). For her, still no spark of anything amiss. Finally after she took what felt like FOREVER getting off her coat, gloves, hat, scarf, etc., she sat on the bed with me and opened the box and said yes (
PHEW, as we had never actually discussed marriage before -- although I was pretty confident of a positive response!
Good luck, buddy ... it's one of the most exciting, memorable and meaningful moments of your life ... good for you, thinking of how to make it as special as you possibly can!
Steve