Do characters of the Middle Ages ever break the boundaries of their roles and exhibit individuality?
I will provide one example for you in the Wife of Bath in Geoffrey Chaucer's Canterbury Tales.
The Wife of Bath is very unconventional for a female of her time. The Wife of Bath is a brazen, overtly sexual, outspoken, very opinionated woman who has been married 5 times. She is on the prowl for her 6th husband at the time of her tale. Before the Wife of Bath begins her tale, she talks about her own life and her many husbands. She fully admits to using her husbands for money and for sex. If she did not get what she wanted from her husbands, she bribed them and manipulated them using whatever means possible to get what she wanted. She also makes the case that women should not apologize for wanting the things they do. They should simply do what they want to do and not worry about what others think and say about them. She also, through her tale, makes the point that what women truly want in a relationship is control...control of their men, so in many ways, the Wife of Bath was unconventional for her day.