Wow, May and Giovanni? Never heard of that before actually. I don't think they ever met in the anime or manga or anything - but that won't stop a true imaginative shipper 8D
Just a note on this thread - it's meant to encompass any characters from anime, games, manga etc, right? Because that's what Pokémon General is for :3 If you meant to make it about characters specifically from the anime, there's another section for that. Just so you know that!
I ship the sort of creepy Yellow and Lance in the PokéSpe manga~ He's older than her, yeah, and they are
mortal enemies, yeah. But they have the same Viridian Forest powers and I think Yellow really affected him in their battle and is at least part of the reason Lance is more of a good guy in later arcs. Helping Silver, helping Gold and all. So I think they share a special connection :3
In the games (and in the manga and anime as well I guess haha), you just can't help but shipping Volkner and Flint.
They are as close to canon as pokémon gets lol