Characters in the anime that you wish met.

[Pokegirl Fan~]

I'd like to see Cameron and Barry meet

 

[xEryChan]

I'd love for Barry and Bianca to meet. I'd also like for Paul and Ursula to meet as well.

 

[Tuskie Tyrant Yoko Kurama]

I'm up for Black and White Team Rocket seeing Butch and Cassidy now. That would be so epic.

 

[johno1995]

Old Team Rocket (the blasting-off-every-episode-Pikachu-stealing idiots) & Cilan
Old Team Rocket & Iris
May & Cilan
Max & Iris
Paul & Misty

 

[LizardonX]

Old Team Rocket (the blasting-off-every-episode-Pikachu-stealing idiots) & Cilan
Old Team Rocket & Iris

You are getting your wish.

 

[Brownie]

Damien and N

 

[Ash&Pikachu-Fan]

Well, Ash met most characters so others I'd like to meet are some of his rivals instead with each other and battles between them would be so cool too!

Lets see; Gary and Paul, Gary and Trip, Paul and Trip, Richie and Cameron, Barry and Bianca, Barry and Cameron, Trip and Cameron but not so sure.

 

[EmphaticPikachu]

Uhm...

don't you know me by now?

Dawn <3...that is all. xD

 

[Pokegirl Fan~]

If the female character from gen. 6 is in the anime, then her and Dawn, she reminds me of Dawn a little.

 

[Lion Demon]

May & Brendan
Dawn & Lucas

I always wanted to know what they'd think of their counterpart...

 

[moneylesswario]

Brock and Cilan
Misty and Dawn
Misty and Iris
Tracey and Cilan
Tobias and Solidad

 

[pokedigijedi]

ash meeting lucas, brendan, hilber, hilda, and jimmy and having them all curb stomp him just to show what a real trainer is made of!

 

[Yuppirox]

Paul and Gary. I guess I wanted to see these two meet, not battle just meet, because Gary's not a trainer anymore so I couldn't care less to see them battle, just meet and interact.
Ursula and Georgia. It would just be funny. And since Ursula has Gabite it would be a legit way for Georgia to get up in her grill. Would be fun to see these two together.
Dawn and Max. I don't know why. I just thought a dynamic of Max thinking Dawn as only second best contest stuff would have made for a funny little moments in the anime. Nothing serious.
Lyra and anybody. Lyra was such a good character she could elevate anyone. Lyra and anbody that is or was a former main character, rival, whatever.
Pachirisu and Emolga. Now they've been together in the same episodes obviously but how on earth do you not have these two electric rodents not interact? To busy pumping up Piplup and Oshawott when it should be Emolga and Pachirisu! This could have been one of the best Pokemon dynamics ever. A electric white squirrel and a flying electric white squirrel. Both with yellow cheeks. Come on writers!
Cyrus and Giovanni. I'd love to see this two just sit down, drink some tea and talk about how crazy and evil they are.
Kenny and Conway. If only because I bet Conway could have somewhat elevate Kenny's character. Conway was that good of a character.

Edit: Final one Drew and Zoey. These two would have had the best contest battle ever.

^^^ALL OF THESE. No, seriously, these are all of my ideal match ups. I never even thought of Kenny and Conway meeting, but now I really wish they had...

Also Misty and Dawn. It just seems right for some reason.