Hello, I will be flying with my fiancée at the end of March on a Saturday morning from BOS - IAD. I have United Gold and I booked him on the same confirmation/reservation. He is a normal member. I listed both of our MP #s on the check in, but it seems it is borrowing from my benefits as he got to sit closer to the front without any fees. What would be the best way to check-in to better our chances of upgrade? I do not mind if only one of us will get the upgrade. However, I would prefer that we both would. I have read so many threads and I am confused as to how to best approach this. As far as when to check in, auto-checkin, speaking to agents at the desk? Any insight would be greatly appreciated. Also we paid for the flight under his cc if that makes any difference.