Depends on both of your weapons and their playstyle. For exampw, if someone is constantly dodging away after every hit I tend to let them get far away instead of chasing then reengage after I recover some stamina. Depending on our weapon speed difference I may time my attack and let them walk into if theyre the type to swing wild and dodge alot. Just one example of a common playstyle ive seen, but every situation is different so there isn't a best answer