First, let me say that I can only talk about my personal experience. I am not a very seasoned theater goer- have been to about 7 shows over past 10 years.
First time, we wanted to see a very popular play and had to pay through the nose and secure the tickets about two months ahead, because we really wanted to see it, and enjoyed it immensely and have not one regret.
On later visits, we were not as particular and either purchased tickets a week or two before or on one occasion purchased tickets from just looking at newspaper ads,when we got there.
We have a friend (single guy) who goes around to the theaters right before showtime and gets a ticket at a reduced price because he says they always have cancellations and try to fill the seat(s) at the last moment. We were concerned that we would get seated in two different areas and never tried it. I also prefer an aisle seat because of a knee problem and didn't think that the odds were very good of accomplishing that.
If you just want to see a play and don't have many preferences about what the play is or who is in it- I would suggest waiting and see what you can find. But if you want a particular play and would be disappointed if you couldn't see it, reserve some tickets. And bear in mind that when you get your program as you walk in, a little piece of paper can flutter out announcing that the understudy is filling in for the star you wanted to see -- it has never happened to us but I guess you have to be prepared for it.
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