So here's the story, but first, some prefaces:
1) I did my best to make her think we weren't going to get engaged for a while; my excuse: I needed to pay down my credit card bills before I could afford a ring. (She actually did believe me.)
2) Several months before Christmas, she told me that she wanted silver hoop earrings just as an idea for what to get her for a present.

So in the month before Christmas, I told her I was taking her on a surprise trip the two days before Christmas. She had no idea where we were going, and it was pretty fun to torment her about this. However, unbeknownst to me, her friends were all suggesting that I was probably going to propose during this trip, and she eventually believed them.

So the day before we left, I gave her a present, which was two tickets to the play Rent in New York. She was really excited, since this was where she hoped we were going. We left the next morning, took a train into the city (had some wine and cheese on the way), checked into the W in Times Square, then went to dinner.

Arriving in Times Square.

Our hotel room at the W.

At dessert (where she was expecting me to propose), I pulled out a jewelry box containing $4 hoop earrings from Wal-Mart. Ouch. She seemed to be a little disappointed (understatement). But she held back the tears, said thank you, and we went to the show.

Going to Rent (Kati's not too happy).

The play was very good, but pretty emotional, so after we got back to the hotel the water works were turned on full blast. She was thinking that given my excuse for not wanting to propose for a while, I was intentionally running up my credit card bills by taking her on a big trip and buying her earrings (I guess she couldn't tell they were only $4) so I would have a continued excuse to not buy her a ring. I told her, "Kati, there's a time and a place for everything." Needless to say, that did not help. So finally she calmed down and we went to bed. The next morning I told her one thing I wanted to do before we left the city was to go ice skating at Rockefeller Center, since I had been there before with my family but never got to get on the ice.

Rockefeller Center.

So we went skating, and I told her that I wanted to get a picture by the big Christmas tree and statue. So we pulled off to the side, got some dude to take our picture, and then I proposed to her right there.

Just before I popped the question.

And just after.

She's happy.

And so am I.

It was pretty awesome, especially since I didn't wipe out and send the ring flying when I got down on one knee (I was very paranoid about this happening before hand). After we were done making fools of ourselves on the ice, we toured around NYC, stopping by Central Park and the Metropolitan Museum of Art.

Central Park.

So it was a pretty memorable Christmas for the both of us, and we spent much of the rest of the break putting wedding plans together.

---