When an Ursaring attack leaves Team Rocket and our heroes in compromising positions, compromise they do, members of each team being paired with members of the other. But such a pairing one would guess to be doomed from the start... and one would be right this time.
Ash and his friends decide to take a break at a nearby lake and relax with their Pokémon out of their Poké Balls. As all the Pokémon are relaxing, they notice something shiny fly through the air. After a few seconds it becomes clear it is a net which opens up and traps all the Pokémon. Team Rocket makes an appearance and announces they have got all their Pokémon and began to fly away. Far away, something attacks Team Rocket's balloon with a Hyper Beam. All the Pokémon are freed when a bunch of Ursaring appear. Ursaring fire Hyper Beam at them all and begin to charge at them. Ash, Brock and Misty recall their Pokémon and run for their lives; Team Rocket following them. They all run into a forest where the Ursaring fire Hyper Beam at them.
After they escape the Ursaring, they realize they have all been split up. Jessie is with Brock, Pikachu and Ash instead of Misty and Meowth and James are with Misty instead of Jessie. Jessie decides to have a Pokémon battle with Ash when a bunch of Ursaring show up again. They abandon their battle and run. Meanwhile, Misty challenges James to a battle when Ursaring also show up and they run. A truce is made between Jessie, Brock and Ash. Ash finds out some information on Ursaring using his Pokédex. Also, Misty, James and Meowth agree to work together.
Ash and Brock call for Misty as Jessie thinks about James and Meowth and wander of they are looking for her. James and Meowth aren't worried about Jessie as they think she is tough. When they reach a crossroad, Misty, James and Meowth suggest going this way but they all point into different directions. When they realize, they play odd finger wins which Meowth wins so they go straight ahead.
Night falls and Ash, Brock and Jessie decide to stop looking as it is too dark to look for Misty. Brock cooks food and Jessie tries it to be surprised it tastes good. She feels upset when she thinks she doesn't normally have such tasty food but doesn't want to tell Ash and Brock so she lies. Misty, James and Meowth are walking. Misty says they should have gone right at the crossroads and James decides to have a break as he is hungry. Splitting a biscuit in half, James and Meowth eat half each while Misty has a sandwich. Noticing James and Meowth drooling, Misty splits her sandwich so they can have some. Misty and James follow Meowth to find a place to camp. In a cliff is a cave which Meowth decides they should sleep in but Misty isn't so sure about it. They are chased out by Ursaring. Ash, Brock and Jessie find a cave to sleep in. Jessie thinks about where she sleeps with James and Meowth. Brock hands a blanket to Jessie to keep her warm and she begins reminisces about her dreams before she joined Team Rocket, while James and Meowth find that they've merely swapped one bossy red head for another one. Misty, James and Meowth play odd finger wins again and Meowth wins again. James has a plan to climb down a cliff into a dark hole in the ground and assures Misty there is nothing to worry about. Meowth decides they should go back and pulls on the rope which lands on his face. Drawing a line in the stone, Misty tells them they can't cross it. Misty has more room on the rock than James and Meowth. James and Meowth plot to steal Misty's Pokémon but don't know how to get away. With Ash and Brock sleeping, Jessie decides to take Pikachu but she bumps into an Ursaring so she runs back screaming.
The next morning, Ash and Brock are trying to find Misty. Jessie complains about not getting Pikachu or any sleep. When Misty, James and Meowth are awake, they realize they are only a few feet from the ground below them where Meowth lets slip they were going to take Misty's Pokémon. Again, they play odd finger wins where Meowth wins again. Confronted by another Ursaring, Ash, Brock and Jessie try to battle it. Ash sends out Cyndaquil and Brock sends out Onix. Onix uses Tackle which gets the Ursaring mad. Cyndaquil uses Flamethrower. Jessie thinks she, James and Meowth are pathetic. Ursaring fights against the Flamethrower and hits its chest. More Ursaring appear so Ash and Brock recall their Pokémon. An Ursaring springs up on Misty, James and Meowth. They decide to run away.
Both groups are running away from Ursaring. They find each other and run across a wooden bridge. The bridge breaks in a couple of places. An Ursaring cuts the rope so the bridge falls, still with them on it; everyone holding onto to someone with Ash gripping to the wooden planks, holding everyone up. Chikorita and Bulbasaur are called out along with James' Victreebel which bites James' head. Onix and Arbok also help. Chikorita, Bulbasaur and Victreebel use Vine Whip to pull up the ropes. Onix and Arbok pull the ropes up with their tails. Just as they are all about to be safe, the rope snaps, sending everyone down below until Chikorita, Bulbasaur, Victreebel, Onix and Arbok save them. Everyone is safe and they celebrate for each other.
The truces are over and they plan to battle. Psyduck is on the wrong side until Misty yells at it. Onix uses Tackle on Arbok. Victreebel uses Razor Leaf as does Chikorita. Togepi is moving its hands from side to side. Meowth uses Fury Swipes. Pikachu uses ThunderShock to stop Meowth. Togepi uses Metronome and produces an Earthquake which causes Team Rocket to blast off.
Afterwards, Ash notices a sign that explained why the Ursaring attacked everywhere they saw one. It read, "WARNING! It is currently the Ursaring mating season and they are using this area as their breeding grounds. Do not disturb them if it's the last thing you do, because if you do, it just may be."
Team Rocket lands where Jessie tells James and Meowth she is unhappy because of them and Meowth says to James they knew they were unhappy because of her a long time ago. Ursaring surround them.