special relativity - Symmetric Time Dilation in Uniform Relative Motion

I feel (and hope) this is an easily answerable question among physicists versed in GR. I promise that I searched for other answers on the forum. Here goes:

Observer 1 starts at X distance from observer 2, moves at 99% the speed of light towards observer 2 and then stops to interact with observer 2.

My questions are:

1. 
   

   Since each observer sees the other as moving slower/faster due to the interchangeability of reference frames, do the slower/faster speeds cancel one another out?

   
   


2. 
   
   

   If so, does time dilation really matter for observers?