I flew for the first time with SW, and the boarding system is just funny. It's simple, I was flying with my girlfriend, we normally wanted to sit next to each other. We managed to do that to our dest, by asking someone to exchange the seats but we failed to do the same on the way back. You have a chance to keep group of friends together if you assign seats during check-in.
I can't think of one good reason for unassigned seats. If it's first come first serve, we booked two months ago, so I came first. Just do what all other airlines do..
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