Josh planned this whole thing! Tiffany had no idea and was just expecting to meet friends for dinner. I was acting as a newbie photographer trying to get some photos of people enjoying the new hotel, or something to that effect. He slipped her the Tiffany Blue Box and the rest is history!
Also, let it be noted that the staff at the Hotel Monaco are incredibly accommodating (and friendly). They went out of their way to open up the rooftop terrace for us and even brought champagne!