Having gotten that out of the way...
How does one get engaged?
Two issues come to mind. 1) The ring and 2) The surprise aspect. Both are very interconnected with one another.
Before I shift to the Jewish Orthodox take on things, I'll sum up a standard, secular take on how the actual engagement process works.
The couple have usually been going out for some time, often enough well over a year (sometimes 2-3 years), each having some sense that this could be the one, and then the guy saves up, secretly buys a diamond ring, and plans an elaborate/romantic means to propose. After he springs his carefully plotted and unexpected spectacle, he drops to one knee holds out the box containing the ring and asks his girlfriend to marry him.
Hopefully (and presumably) the girl says yes, unlike this poor guy. For the record, I don't think sports and engagements go well together, unless the girl is as big as, or bigger, fanatic than the guy is.
In the Orthodox Jewish world, things are different. The dating time frame is usually shorter, typical "YU procedure" is around 6 months dating before engagement, but that amount of time varies per individual case. The engagement itself is usually known in advance (to one degree or another), so often there are no major surprises. Sometimes wedding plans have already begun before any official announcement is made.
Which gets me back to the ring. Seemingly, the guy has to secretly find out the girl's ring size, as well as preferences and then pick the ring that fits his budget. However, how can he guarantee that the girl is going to like it - this is something she will hopefully wear for the rest of her life. I would be horribly nervous to get a ring that the girl ended up not liking, which would create a conundrum. Either a) she sucks it up and keeps the ring because of its sentimental value, though I wonder if this could become a point of contention later (I hope women aren't so petty) or b) she actually exchanges the ring for something she likes, which totally ruins the whole emotional impact of the ring itself.
The easy solution is to have her pick out the ring beforehand via Blue Nile or wherever. But if she knows what ring she's getting, doesn't that also let her on to the fact that a proposal is coming in the near future? Even if the guy then delays the proposal for some time, the girl will certainly have her curiosity aroused any time he does something suspicious.
One way around this conundrum, which makes a lot of sense to me, but requires more money, is to get her a bracelet first as the proposal item, then go pick out the ring together. I would hope that the particular bracelet he chooses (hopefully with female help) isn't so horrible that she might exchange it for another (though I did recently hear about a story where the girl did just that - with her fiance's permission). Then, she also gets to pick the ring that she likes and will cherish until 120. Though I could foresee some issues arising with regard to her liking a particular ring/diamond and his finances only going so far...
Anyway, back to the proposal itself. I've heard of/seen good ideas as well as some not-so-great and even bad ideas. The good ideas usually have something to do with a meaningful venue or other "thing" that has been a part of the relationship. I think that this is an example of a very well done, almost perfect in every way proposal. Chana's recent engagement is also a very picturesque story. Other examples I've encountered include:
A banner seen while sky diving, holding a banner/flowers while waiting at the airport, popping the question on a plane and having the pilot announce that they will not land until she says yes, the ring placed in a glass of champagne, an Old City of Jerusalem rooftop overlooking the Kotel plaza, spelling out the question using Bananagrams (saw this on two different occasions, actually), asking during a romantic dinner, and even just asking casually (anyone seen the famous Rocky II scene?).
One friend told me he had this shtick where he would always ask the girl he was going out with to get something from the glove compartment of his car, starting with the first date and periodically throughout their shidduch. This lured her into a false sense of security that retrieving things from the glove compartment was a totally normal thing to do. Thus, when he popped the question, she had no clue - and it worked for him.
The recent engagement I referenced above in the caveat involves a staged arrest with local law enforcement. I've seen pictures, but I heard more details from a first-hand source who was there taking pictures. While my friend and his soon-to-be fiancee were sitting in his parked car, a cop drives up and asks him to step out of his car. The policeman asks him a bunch of questions, physically searches him, and basically prepares to slap on the handcuffs and haul my friend off to jail. The girl, in the meantime, is crying and understandably freaking out. The officer asks my friend if he has any last thing to say, and he pulls out the ring and proposes.
Granted, she said yes, but I really don't think this sort of thing is a good idea. His original plan had something to do with planting a security risk item inside her carry-on at the airport and pulling a similar stunt using airport security. The other friend who related the proposal story told me he quickly nixed that when my engaged friend suggested it - and I think that was the proper course of action.
Anything that involves scaring the girl to tears is not worth it, in my opinion. Certainly, figuring out something clever and poignant (with personal in-jokes perhaps) is the goal, not to frighten her to death and then scream out "gotcha!"
A close friend who is part of the Lakewood crowd recently got engaged and I asked him about all the details. He simply proposed in a park, without any jewelry on hand. But a short while later when they got back to the car, he had 3 bracelets prepared for her, and let her pick the one she wanted - apparently in Lakewood there are these really heimishe jewelry stores that let you borrow a few items of jewelry, then you let the girl pick the one she likes, pay for it, and return the other ones. I think that's a pretty neat idea! Though it would definitely require a very specific kind of store to let you do that
As a side point, he also told me that there is a car rental service in Lakewood that guys use for dates that gives you a free upgrade every 10 dates. In addition, if you actually get engaged to a girl while using their car, they take your name and add if to their list of satisfied customers, haha.
Any married readers want to weigh in on this? Unmarried readers are welcome to share what they envision happening as well.