Bennett didn't want me to know when the proposal was going to happen. I already knew he got the ring due to a mishap with the shop worker, so the day had to be a surprise. He planned several very elaborate and romantic dates leading up to the one where he'd eventually propose to throw me off. On the day he proposed, we started our date on a dinner cruise in Chicago where we smoked cigars and ate incredible food. Then we went to the Skydeck at the Sears Tower. Bennett told me he was leading us back to our car so we could head home, but he took me to Virgin Hotel where we liked to go for drinks and board games whenever we visited Chicago together. Luckily I'm terrible with directions because I had no idea that's where we were. He asked me to turn and look at the sign and when I turned back to him, he was on one knee. I think I managed to squeak out a 'yes' before hugging him.