What is the ruling on the chatting between a young man and his girlfriend?
Private chatting between the two sexes entails religious violations, and leads to prohibited attachment.
What is the ruling on someone who perform their prayer after finishing it because they believe they missed a Rak'a, a prostration, or that they did not perform it correctly (thinking their prayer was invalid)?
If he was sure that his prayer is void then reperforming it is an obligation along with figuring out the reason of invalidity so long as this wasn't out of uncertainty. And Allah Knows Best.
Should one obey his mother even if she was wrong?
Obeying one`s mother is an obligation in matters that are beneficial to her and so long as she didn't drive her children to commit an act of sin.
Is it incumbent on the fiancée to obey her fiancé?
When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).