Date Expectations (Japanese: ころがれ！恋するドンファン！Roll! Loving Donfan!) is the 114th episode of the Advanced Generation series, and the 388th episode of the Pokémon anime. It was first broadcast in Japan on February 10, 2005, in the United Kingdom on January 30, 2006 and in the United States on April 1, 2006.
May and her friends are headed to Pacifidlog Island for the last Pokémon Contest before the Grand Festival. But their boat has engine trouble and the pilot, Carlos, lands on a nearby island. To reach Pacifidlog in time, our heroes must cross the island to the port and take a ferry. But the island is full of Donphan, and it's breeding season—all the male Donphan perform a Roll Out dance of love to impress the females, which can be dangerous for any Trainers who happen to be in the way!
Along the way, May and her friends cheer on a Donphan who wants to impress a brown female Donphan. Snorunt's Ice Beam turns the ground into an ice skating rink, and Donphan trips. Ash chases Snorunt, who won't go back into its Poké Ball, but just as he gets it back, the Donphan send everyone running! May and Ash make it to the port as the last ferry is about to leave... and May bravely decides to turn around and look for Max.
May's Grand Festival debut will have to wait another year, but everyone is reunited, along with their Donphan friend and the brown Donphan. Donphan does a dance of love that wins her heart, but Team Rocket shows up and captures them both. May, fed up with Team Rocket's constant schemes, calls on her Pokémon to free the Donphan and stop Team Rocket. Once the Donphan are freed, they Roll Out together and Team Rocket blasts off yet again.
Carlos finds May and her friends sadly standing at the port. His boat is fixed, and he takes them to Pacifidlog. Now it's up to May to win her fifth ribbon!
Carlos informs Ash and his friends that they are an hour away are from Pacifidlog Town, site of May's next Pokémon Contest challenge. Two islands come into sight, and the engine breaks. They land on the left island, Donto Island, while Carlos fixes the engine. He tells Ash it might take a few hours to fix, and tells them that if they want to be on time for the Contest, they could take a ferry on the other side of the island.
Soon, they come across a group of Donphan using Rollout, and almost get run over. Brock explains that it is mating season, so the male Donphan are aggressive while trying to impress the females. The same Donphan rolls towards them again, so they run away and leave the area. When they find a deserted area, they stop to rest. Suddenly, a female Donphan shows up and a bunch of males come over to impress it. Ash and his friends run away again. They call out Mudkip and Corphish to protect them, since Water types are super effective against Ground types.
Meanwhile, Meowth spots an opportunity and tells his teammates that they should give the Donphan to the Boss. As Meowth suggests the Donphan would make for a replacement bowling ball or a great back massage, James reminds him that Donphan are rather destruction. Jessie pulls them both into line, declaring they need to give something to the Boss. They start setting up some nets as a female rolls by. They try to figure out where it was going, but get squashed by more males chasing it. Jessie tells James to have Chimecho heal them, but it decides to use Astonish, frightening Jessie and Meowth.
Ash and friends notice some Donphan with mates up ahead. Everyone comments on them, but another Donphan starts rolling towards them. The Water Pokémon attack it, and knock it into a rock. Brock bandages its trunk, but suddenly a Shiny Donphan comes over and the injured Donphan chases after it. Later Ash sees the injured Donphan again as it tries to impress the Shiny female, but it just gets knocked out of the way by some other Donphan. As they watch, Snorunt comes out of its Poké Ball and uses Ice Beam on the surrounding grassland. Excited, Ash tells it to use the move again, and it freezes the ground under the Donphan, making them slip. The Shiny female expresses its disapproval of all the potential mates and walks away. Max says they shouldn't have brought out Snorunt, but it runs off as Ash tries to recall it.
Meanwhile, Team Rocket has made a pitfall trap, and they're all congratulating each other. Unnoticed, Snorunt walks up and freezes them in ice. Before the ice can melt, more Donphan roll by and crash into them, blasting them off. Afterwards Ash manages to recall Snorunt back to its Ball. Another horde of Donphan roll towards the group, forcing everyone to flee. Brock and Max run one way, while Ash and May go the other. During their search, Ash and May reach the port just as the last ferry to Pacifidlog is about to leave. May, however, tells Ash that she won't get on, because even though she'll miss the Contest, she won't leave her brother. She remembers leaving her house and promising her mom to take care of Max, and Ash agrees. May begins tearing as the ferry leaves port, making her realize that she will have to begin her quest to the Hoenn Grand Festival all over again. She quickly wipes away her tears and suggests they keep moving.
Brock and Max see the injured Donphan, and ask it if it had any luck. It tells them that it didn't. Meanwhile, May and Ash spot the Shiny female. May gives it some Pokémon food and tells it about the injured Donphan. Following the injured Donphan, Brock and Max soon find Ash and May alongside the female Donphan. The injured Donphan enters into another Rollout, but is knocked away by another male. All the other Donphan start rolling around the female, but the injured Donphan gets annoyed and knocks them all away. As the pair roll off together, Team Rocket appears and nets them both. Ash wants to battle them, but May interrupts and scolds the Rocket trio, complaining that she would be in Pacifidlog if it wasn't for them. Team Rocket gets worried and confused by May's rage. May sends out her Pokémon. Beautifly pulls the Donphan away with String Shot, Bulbasaur cuts the net with Razor Leaf, Skitty uses Double Slap on them, and Combusken uses Fire Spin. Finally, the two Donphan use Rollout and blast Team Rocket off again. Everyone thanks them and congratulates the injured Donphan on getting the Shiny female. Both Pokémon smile.
By evening, the group reaches the harbor. As they look at Pacifidlog on the horizon, Ash says that they could have done it but May wouldn't get on the boat without Max. Max apologizes to his sister, but May tells him it's okay and that she was happy that she saw the two Donphan roll in love together. Suddenly, they hear Carlos calling out that he fixed the engine, so they get on board the boat. While they head towards Pacifidlog, Carlos remarks that they are lucky because if he hadn't gotten there then, he would have thought that they got on the ferry. Max tells May that now she can be in the Pacifidlog Contest, much to her excitement.