Mindi if you are traveling on UA or Skywest, you can not be in the same reservation. Unless you have him traveling under your companion pass otherwise if he is using a retirees passes he will be a 8c you Use your passes
and he will be a 8a (which is a higher seniority) So as far as requesting seats together you can ask at the gate...but you are pretty much going to get what is left. Hope that answers your question, Heidi