I wanted to ask to what extent is a husband supposed to listen to his wife?

And also is it a reasonable request to ask him not to go out with his sisters friends even though he is with his sister and his parents are okay with him doing so?

Islam has emphasized to behave well with the wife, it is the duty of the husband not to torture her. In the rest of life, both should live together in harmony and forgive each other's shortcomings.