Dear Confused and Frightened -
I think your dream does reflect some of the feelings you are having as you graduate from middle school and prepare for high school. It is a time fraught with new concerns. High school can seem big and ominous, and certainly unknown. You will be leaving behind your old school, some of your friends may be going to another school (so you won’t see them as much either), and you also, when you get to high school, will be put in with a group of kids all of whom are older than you - or older than your class, at least.
Dreams frequently use the metaphor of death to indicate change or metamorphosis. In this sense, your graduation from middle school can be seen as a “dying.” You are leaving behind certain aspects of your life for good, and soon you will be embracing the new experiences that high school will bring to you.
Your dream, and the fact that it recurs, indicates that you are concerned about this transition. In the dream you want to escape the ceremony, which suggests that, in real life, you may wish you didn't have to go through with it all.
You ask about the wine glasses in the dream, and I think they are a very interesting symbol. Wine in Christian religion is a symbol of metamorphosis. Christ instructed his disciples, each time they ate bread and drank wine, to remember him at this time. The wine, he said, is my blood. The bread is my body. And today, still, if you attend a Catholic or other Christian ceremony, this “ritual” is frequently repeated. It is called communion. When people choose to participate in communion, they symbolically share the presence of Christ through drinking his blood (the wine) and through eating his body (the bread).
I think it is significant that, of all the keepsakes and valuables that you could have taken from the temple, you choose to keep the four wine glasses - one for you and each of your best friends to remember the night by. Instead of holding on to the past (keepsakes, valuables) you choose instead to embrace the symbol of change. It suggests that you already understand this process of change - and that you know how you are going to survive this next period. You will grow and learn, just like you have already done so many times before in your life. And your friends will be with you, and you will be growing and learning together.