Wow, it seems that you are going to date someone you like. Anyway, personally speaking, it would be absolutely ok to date a girl with glasses, I am going to date a girl with my cool black glasses, and she thinks I am simply her very type. So, it doesn't matter if you wear what or what, just be yourself. Maybe sometimes you need to consider your overall style.
LOL, I think your question is very interesting. If I were boy, I would love to date with the girl with glasses, because I think girls with glasses are very cute, just like me. Lol. The most important is that whether you love her, if so, every other reason is not important. Moreover, the glasses have becoming a trendy; you know many famous stars prefer to wear the frame (without the lenses because there is no prescription of their eyes). At the same time, many girls are will to make them more beautiful with the help of the glasses, as the glasses can make our face smaller, the eyes bigger as well. If your girl is with the glasses, you will think she will be less beautiful without a pair of the glasses. Besides, many people regard the glasses as a symbol of wisdom, because they can know the people with glasses have read many books and are filled with knowledge.
Different people have different taste. And I will date the girl with glasses. Some girls will look more beautiful when they wear the glasses. They will look cute and lovely. I believe some guys have tends to love the girls with glasses. Thus, this question is hard to answer because of the different taste.
It depends on the girl, some do and some don't. I find that most girls don't look that great in just regular frames but if they change their frames to something more unique yet stylish or get contacts it usually helps. But again, depends on what she looks like.