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For Enderbro, I'll make him post-game. For Maker, I'll make him Johto post-game. They're way too overleveled. Or maybe have them be in a battle facility?

Season 1 Episode 5

Halfway Point

Shimoro: ! *walks over to Red and Blue* I'm a cool kid! I have a girlfriend!
He: ! *walks over to Red and Blue* Hi! I like shorts! They're comfy and easy to wear!
(A Multi Battle starts.)
Aqua: *quietly* Hold up. Let me heal our Pokemon first... Go, Pidgeot!
(Red sends out Pikachu.)
Shirmoro: Go, Houndour!
He: Go, Gallade!
Shimoro: Houndour, use Roar!
Aqua: Wha-- isn't that negative priority?
Raticate was dragged out!
He: Gallade, use Close Combat on Raticate!
Aqua: ...
Fire: ... (Pikachu, use Discharge!)
Aqua: Red! What are you doing?! ... Go, Pidgeot! Use Mirror Move on Gallade!
A critical hit!
It's not very effective...
Gallade fainted!
Aqua: Yes!
Ironical He is out of usable Pokemon!
Fire: (Pika, use Thunderbolt!)
Houndour fainted!
Shimoro: Go, Mareep!
Fire: ... (Come back, Pika! Go, Ivysaur!)
Aqua: Come back, Pidgeot! Go, Charmeleon!
Shimoro: Mareep! Thunderbolt on Charmeleon!
Fire: (Ivysaur, use Sleep Powder!)
Mareep fell asleep!
Shimoro: Come back Mareep! Go, Pikachu!
Aqua: Charmeleon! Use Slash!
A critical hit!
Shimoro's Pikachu fainted!
Shimoro: ... Go, Mareep.
Fire: ... (Leech Seed!)
Aqua: ... (Ember!)
Fire: (Come back, Ivysaur! Go, Pikachu! Use Volt Tackle!)
Mareep fainted!
Shimoro is out of usable Pokemon!
Shimoro: You're talented Pokemon trainers!
(Battle sequence ends.)
Shimoro: I know a good place if you want to show your Multi Battle skills! Follow me!
(They follow him to Saffron South Gate, where the guard does not let them pass. They then take the Underground Path to Cerulean, where they head east to Route 9.)
Shimoro: Okay. I know how to navigate Rock Tunnel. Just follow me, okay?
(They follow him as he goes up and down ladders, until they finally reach Lavender Town. They then take the OTHER Underground Path to Celadon City.)
Shimoro: Here it is! Cerulean Gym. Today, they have a visitor, who specializes in Ice types, and you must have a Multi Battle Partner to challenge the Gym today! *leaves like NPCs do*
(Fire and Aqua proceed to enter the Gym--)
Old Man: Nihihi! This Gym is good! Nothing but girls!
Fire: ...?!?
Aqua: Don't worry. I'm sure you'll find plenty of girls to reject you... ANYWHERE!!
Old Man: ...!!
(Fire and Aqua enter the Gym.)
Gym Guide: Yo, champs in the making. Today's a little different, as we have a visitor. Usually, you go solo, but today, the Leader battle is a Multi Battle, so you'll need a partner. Since this is Celadon Gym, you'll need to stay quiet. Got that?
(Fire and Aqua nod. Fire takes the left route while Aqua takes the right.)
Kalisa: Hi! By boyfriend is cool! Go, Bellsprout!
(Battle begins.)
Fire: (Go, Charmeleon! Ember!)
(Bellsprout faints.)
Kalisa: Go, Oddish!
(Oddish faints to Ember.)

Meanwhile, on the right path...
Lori: YOU MAY ONLY CHALLENGE-- I mean, you may only challenge the leader if you show me a cute Pokemon! GO, Exeggcute.
Aqua: Go, Charmeleon!
(Exeggute faints to a super-effective Ember.)

(Fire and Aqua both move on by cutting the tree blocking the path.)

Erika: ... *wakes up and sends Victreebel*
???: Go, Jynx...!
Fire & Aqua: (Go, Charmeleon!)
Aqua: Red! The other trainer specializes in Ice Pokemon! Let's target them, so my Pidgeotto can take care of Erika's grass types...!
(Jynx outspeeds and Psychics Fire's Charmeleon, before geting Ember'd by both Charmeleon, fainting. Victreebel poisons Aqua's Charmeleon.)
???: Go, Lapras...!
(Both Charmeleon outspeed and Metal Claw Lapras, which resists it despite being an Ice-type with its armour. Victreebel Giga Drains Aqua's Charmeleon. Lapras uses Surf and both Charmeleon faint.)
Fire: ... (Go, Pikachu! Volt Tackle on Lapras!)
(Lapras faints.)
Aqua: Go, Kadabra...! Use Confusion on Victreebel.
(Victreebel faints.)
???: Go, Cloyster...!
(Erika sends out Tangela.)
Fire: (Pikachu, Thunderbolt that Cloyster!)
(Cloyster faints.)
Aqua: Kadabra, use Confusion on Tangela.
(Tangela loses 1/3 HP and uses Giga Drain, restoring 1/6 HP.)
???: Go, Glaceon...! Use Freezy-Dry on Pikachu...!
(Pikachu almost faints.)
Fire: ... (Come back, Pikachu! Go, Ivysaur!)
Aqua: Kadabra, use Disable on that Glaceon!
(Freeze-Dry was Disabled!)
???: Damn it!
Erika: Use Giga Drain on Kadabra...
???: Glaceon! Use Freezy Frost on Ivysaur!
All: What?
(Ivysaur faints.)
Fire: ... (Go, Wartortle, use Bite on Glaceon!)
Aqua: Kadabra, Disable Tangela's Giga Drain...!
(Giga Drain was disabled!)
Erika: Tangela... use Constrict on Kadabra...
(Kadabra goes down to half HP.)
Fire: (Wartortle, Bite Glaceon.)
(Critical hit!)
???: ... (WAS THAT THE BITE OF +6 252+ Atk Wartortle Black Hole Eclipse (120 BP) vs. -6 Lvl 1 0 HP / 0- Def 0 IVs Glaceon on a critical hit: 61443-18316 (512025 - 152633.3%) -- guaranteed OHKO?!?)
Glaceon fainted!
??? is out of usable Pokemon!
Aqua: Kadabra, come back! Go, Pidgeotto! Use Gust!
(Tangela nearly faints, uses Constrict on Wartortle, and faints to a second Gust.)
Erika: ... Go... *sends Vileplume, which uses Giga Drain on Wartortle, leaving it with a sliver of health.*
Fire: (Come back, Wartortle! Go, Ivysaur!)
Aqua: Pidgeotto! Use Gust (again)!
(Vileplume loses 1/3 of its HP, then uses Acid, which causes Ivysaur to also lose 1/3 HP.)
Fire: (Ivysaur, use Razor Leaf!)
(Razor Leaf barely does a scratch to Vileplume.)
Aqua: Come back, Pidgeotto! Go, Kadabra, use Confusion!
(Confusion crits and faints Vileplume.)
Erika: Go... Leafeon...
Aqua: Use Confusion (again)!
Fire: (Ivysaur, use Razor Leaf!)
(Razor Leaf does a critical hit, but it barely affects Leafeon, which uses Sappy Seed on Kadabra, almost fainting it.)
Aqua: Kadabra, use Confusion (again)!
Fire: (Ivysaur, use Razor Leaf!)
(Razor Leaf crits but still barely affectly Leafeon, who prepares to Giga Drain, but Kadabra faints before it can...)
Aqua: ... ... ... ... Go, Pidgeotto! Use Gust!
(Leafeon faints.)
Erika: ... ... ... *wakes up* Oh! I concede defeat. You are remarkably strong. I must confer on you two the Rainbow Badge.

Season 1
   Episode 5
       Halfway Point
           THE END

...to be continued...

Hey! Since this is the 5th episode AND the 4th badge, I'm just gonna list off the MCs' teams, similar to how Pokemon Adventures (the manga) does at the end of every volume. I didn't really base them of anything, just listed what I think their teams would look like. It might include some mistakes.

Fire:

Pikachu
Lvl. 24
Lightning Rod
No Item
-- Volt Tackle
-- Thunderbolt
-- Discharge
-- Quick Attack

Ivysaur
Lvl. 28
Overgrow
No Item
-- Razor Leaf
-- Sleep Powder
-- Leech Seed
-- Growl

Charmeleon
Lvl. 30
Blaze
No Item
-- Metal Claw
-- Ember
-- Slash
-- Smokescreen

Wartortle
Lvl. 26
Torrent
No Item
-- Water Gun
-- Bite
-- Withdraw
-- Rapid Spin

Leaf:

Wartortle
Lvl. 20
Torrent
No Item
-- Bubble
-- Withdraw
-- Tail Whip
-- Bite

Aqua:

Pidgeotto
Lvl. 29
Keen Eye
No Item
-- Gust
-- Sand-Attack
-- Quick Attack
-- Whirlwind

Kadabra
Lvl. 28
Synchronize
No Item
-- Teleport
-- Confusion
-- Kinesis
-- Disable

Charmeleon
Lvl. 30
Blaze
No Item
-- Metal Claw
-- Ember
-- Slash
-- Growl

It's probably not a star. I predict it will be... 5 coins.

Sabrina's Shyster colour is supposed to be magenta. And Veenyx's is supposed to be jade. I think I may have forgotten to mention that Nommanic has dark brown hair. Oh, and that's not how his hat is supposed to be...

Everything else looks great.