I have always wondered this. Did any of Ash's friends watch him in the Sinnoh league? We know Oak and Delia did, but we can't say for sure any of his friends did because they weren't shown.
As shown at the end of AG and DP, Ash doesn't even take the time to let his old friends visit him before he's off to a new adventure again.
As shown in the Dawn and Brock specials, neither of them made a mention of Ash and I don't think they know about Iris/Dento at all.
Was Misty ever aware Dawn existed? Considering they've never met and there was no Pallet visit, Misty probably doesn't even know about that character, let alone Iris/Dento. Do you think May actually cares what Ash is doing anymore at this point?
I think we may never know.
As shown at the end of AG and DP, Ash doesn't even take the time to let his old friends visit him before he's off to a new adventure again.
As shown in the Dawn and Brock specials, neither of them made a mention of Ash and I don't think they know about Iris/Dento at all.
Was Misty ever aware Dawn existed? Considering they've never met and there was no Pallet visit, Misty probably doesn't even know about that character, let alone Iris/Dento. Do you think May actually cares what Ash is doing anymore at this point?
I think we may never know.