Top 10 pokemon characters Id like my OCs to meet

Here are a list of one off or reoccurring human pokemon character's  I could see my main OCs Josh and Tom ( Not my trainer OCs Mike and Emily) meeting during the pokemon crossover arc in my OC cannon.
Characters I'm fond of and can see my OCs getting on well with. I should also make a note that I'm only sticking with characters I like from the era's I grew up with from Kanto to Hoenn.

In no particular order.

UPDATE I replaced Jenny and Joy with Sakura and moved them to the honourable mentions. In my heist making this I forgot al about Sakura.

1. Delia aka Ash's mum. Seems right for Josh at least to meet Ash's mum , as Josh forms a strong brother like friendship with Ash.

2. Richie and his Pikachu Sparky.

3. Clair the Black torn city GYM leader and dragon pokemon trainer. I'm sure Josh would maybe get on her good side as he as sort of Dragon/ dinosaur themed armour and as control over a dragon like dinosaur the Dragonsaur. Plus.. I must admit I think Clair is bit of a babe ...  

4. Cassidy and Butch. AKA Jessie and James done right. One funny thing I can see happing is Butch thinking Josh or Tom got his name wrong and starts ranting, and Josh or Tom say "We said Butch you daft sod!"

5. Duplica. I remember really enjoying her character as a kid and was happy to see her again in the Johto era. And I can see Meg having a lot of fun with her Ditto. 

6. Lily. No not one of Misty's bloody sisters ... Who I hate. The Lily from the episode Hocus Pokemon in season 5.  For one thing she had a British accent (Though she said yoghurt the way Americas do) So Josh and Tom would like to meet a fellow Brit during their time in the pokemon world. 

7. Jasmine the Olivine city leader. Like Clair I think she's on the very pretty side. And I can see Meg getting along with that little girl apprentice of Jasmine's Janina.

8. Sakura. One thing I like about her is her friendship with Misty. So if Josh and co met her be a cause of anyone who is a friend of Misty is a friend to Sakura.

9. Professor Oak. Well would seem fitting and he could tell Josh and Tom about pokemon given Josh and Tom are from a time before pokemon exited.

10. Brendan. Yeah sure he didn't have a proper appearance in the main pokemon anime , so my OCs meeting him would give him a chance to shine.

Honourable mentions.
The many Officer Jenny's and Nurse Joys. Well it'd be impossible for Josh and co not to meet them given their all over the bloody place in almost every region.
Molly Hale
Melody from the 2nd movie
Professor Elm
Professor Birch
Lance
Liza
Lara Laramie
Casey
Tyson and his Meowth in boots


UPDATE new honourable mention added


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