Originally Posted by
roknroll
Not necessarily. You can book yourself and one parent on a single reservation and the other parent on their own reservation. The upgrades should be requested automatically when booking (make sure to check the 'request upgrade' box) so you won't have to call in to DL. The companion must be a SkyMiles member, so make sure your parents are signed up with a DL SkyMiles account and enter their info in at booking.
You are correct, of course. I missed that he had not made the reservations already. Of course, being on the same reservation as the companion, pulls down his chance at the upgrade for himself.