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I have been trying to group up with my brother to do pledges but lately it doesn't allow me to do so. I queue in as a healer and my brother as a tank is this work as intended?
To answer you question, it SHOULD work as intended. As long as in the Group option, you're selecting the Healer icon and your brother is selecting the Tank icon then it should be working. Obviously, you'll have to wait until 2 DPS also get locked into your group, but with the amount of DPS it should (again, that word) find them fairly quickly.
When grouping with my brother and I try to hit the Join Queue button nothing happens
Do you see any errors? I know on console you'll see a message in the top-right corner of your screen if something goes wrong. If two people have the same roles (not DDs), it won't queue and you'll see a message displayed to you.