Whether you both could get in depends on how many tickets you were trying to get, ultimately.
Each account can hold up to 2 tickets to any given event, by default. So if I set up a wishlist for 1 ticket for me and 1 ticket for you - and you do the exact same thing - then we both could in theory end up with 2 tickets to the event.
If, however, I put 2 tickets for myself on my wish list and you put 2 tickets for yourself on yours, then that would complicate things if we also tried to buy tickets for the other person as well. What kind of problem that would cause (if any) would depend on whether each of us had selected "only get tickets if all are available" or not.
Once tickets get added to your carts, you can both check in with each other and drop any excess tickets, of course - and that's part of why y'all shouldn't be too concerned if you don't get your first event picks - some things are likely to open up.
Does that make sense?
And "connected" events just refers to adding someone as a friend so you can buy them tickets or they can do that for you. That allows someone to plan events for a big group of friends without having to get a million tickets in their own name.
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Derek Guder
Event Manager
Gen Con LLC