It sounds like to me your friend didn’t want to sit with you because you said he has flown Southwest before. He would have known about the boarding pass procedure since they have been doing it that way since the Airlines started in 1971. Maybe next time you fly an airlines you’ve never flown before you should do a little research if sitting with your friend is so important because there are other airlines that do the same thing. Second, when I’ve flown Southwest I’ve seen the gate agents let groups that had both A & B boarding passes board together in the A group, you just have to ask.
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