After Ash accidentally destroyed May's bicycle (like he had done with Misty's), she is initially angry, but when she sees Ash sleeping next to Pikachu after taking care of him all night she forgives him, and begins to like him. Later, May asks Ash to let her travel with him, and when he accepts, she is visibly satisfied.
When the duo arrives in May's hometown, she goes to great lengths to ensure that Ash doesn't discover that her father is the Gym Leader, perhaps for fear that he will start treating her differently. When May offers him to go to lunch, Ash immediately accepts, stopping to look for information on the gym. During the meal, Ash and May chat amiably, and Ash becomes May's mentor, explaining how to capture and fight with Pokémon. When Ash decides to spy on Team Magma's actions, May refuses to be left alone and accompanies him, despite the danger.
When Ash decides to spy on Team Magma's actions, May refuses to be left alone and accompanies him, despite the danger. When Ash discovered the truth about May's father, he didn't get angry with her.
When Team Rocket steals May's Torchic, the girl falls prey to despair; Ash crouches next to her and tells her not to worry, promising her to recover Torchic, which he does. When May's little brother Max expresses his desire to travel with Ash and May, neither of them seems happy, a sign that perhaps they wanted to travel together alone.
When she gets hungry, May asks Ash where their food was; when the boy replies that he has not thought about it, and declares that to deal with these things, first was his friend Brock, May gets offended a lot and apologizes in a sarcastic tone for not being a useful travel companion like Brock. The three later met Brock, and he noted a great similarity between Ash and May.When a Taillow is about to attack Ash and his friends, Ash confronts May to protect her.
When May decides to become a Pokémon Coordinator, Ash is the first to give her unconditional support. During Ash's first fight in the gym, she is visibly very anxious, and after his victory she holds her hands together, and has a big smile on her face.
When Ash and May discover that Max could be in danger, because of Team Idro, May is very worried and only recovers when Ash comforts her, she is relieved. This is the first of many scenes in which May seeks comfort and reassurance from Ash, although she could very well give him Brock, or someone else, a sign of the great trust that the girl has in him.
Ash, May, Brock and Max end up in a deserted place where there are no boats or ferries to reach the island, where Ash's next Gym battle will take place. They manage to find only a deserted harbor and after hearing Ash burst out that he was really looking forward to his next Gym battle, May says determined that he will find a boat. While looking for her, May looks towards the sea and thinks that Ash should not have used that rude tone with her. When the group arrives on the island, May decides to get in a bikini as soon as she arrives on the beach. However, instead of running down to swim, she poses in front of Ash and his brother and asks what they think. Ash seems to be embarrassed by the situation.
Drew, May's rival, criticizes his abomination as a coordinator, and Ash immediately begins to defend her clearly angry. After May loses his first Pokémon Race, Ash blames himself for his defeat. He says: "It's my fault, I wish I'd spent more time with May, teaching her". Later, May cries backstage and even though everyone tries unsuccessfully to cheer her up, Ash is the one that puts the most effort into it. Ash and May seem to hold, much to each other's competitions.
May asks Ash for a battle, and although he is surprised he accepts, but a former coordinator Julie, suggests May to fight against her and the girl accepts. During the battle, Ash seems to cheer for May, and when he loses Ash he seems worried about her and her Skitty. Later, Team Rocket tries to steal Numel and Ash and his friends try to stop them with the result that May ends up trapped by Team Rocket's car and Max is very worried. Ash promises that they will save May by swearing it to himself. When May falls off a cliff and can barely hold on to a branch to save herself, Ash is visibly worried about her and promises to save her. While everyone else is holding the rope, Ash descends into the chasm, and grabs the girl's hand. Both are brought to safety, but even though everyone has collaborated Ash is the one who risked the most to save May. When May decides to interrupt their journey to heal a wounded Swablu, Ash tells her: "You will take all the time you need to help your friend," even if it takes a long time to get to the next gym. Also, when Max talks about May's past crush, she immediately silences him, perhaps not wanting Ash to know about her past crush.
When Max asks her if she wants Ash or their father Norman in their Gym fight, May is very doubtful and upset and says, "Sure, I want dad to win ... but I don't want Ash to lose!" making Max very angry that he immediately plays with Norman. After Ash lost a fight against coach Poncho, May gave him advice on the fight that the boy exploits during the rematch with Poncho. May still seems doubtful about who to support in the fight in the gym.
During the clash between Ash and Norman Pikachu is hit, and May tries to help Ash by telling him to replace him, and when Brock says it wouldn't be a good move, May stops her mouth with terrified hands. At several points during the battle, May looks worried and scared when Ash is losing and happy when Ash is winning. This implies that May chose to support Ash and not her father, at least in the subconscious, which is externalized when after Ash's victory, May rejoices, while Max is very upset.
Ash and May come across Oscar and Andi, a young couple who believes they are in love; the two quickly deny it with the same words, and the same gestures, which consolidates the opinion of Oscar and Andi and causes further tensions between the two, who begin to quarrel allegedly due to the embarrassment caused by them by Oscar and Andi . After a double battle against Jessie and James in the end, Ash and May shyly apologize to each other for their discussion, before sunset.
When May gets lost in a territory populated by Grass Pokémon , Ash once again goes to save her despite warning him that this place is dangerous because of the ferocious Grass Pokémon. Ash arrives just a time to save May from the Pokémon that were about to attack her, after which he grabs her by the hand and runs off with her. The two hold hands all the way.
When they meet Ash and May's Bulbasaur show signs of mutual appreciation, (a ship called VineShipping). During the episode, May makes several comments about how the two Bulbasaurs are a great team. When Ash returns his Bulbasaur to Professor Oak, he caresses May's Bulbasaur on the head with his liana. This their relationship, supports the Advanceshipping, since according to some experts the Pokémon represent the feelings of their Trainers, and that when two Pokémon fall in love, there is a good possibility that also happens to their trainers.
When May is sullen on a bench for losing a race Ash goes to console her, succeeding. Ash is known for being reckless and irascible, and he is not one who apologizes easily, yet, almost always appears sweet and protective of May. For his part, May always shows great concern for Ash, when the boy is in danger, far superior to that of his other traveling companions.
When Harley an opponent of May embarrassed her during a race, and she lost focus, Ash encouraged her by helping her achieve victory. After her victory, May thanks Ash declaring that if it hadn't been for him he would have lost, but Ash tells her that it's all thanks to him.
May keeps Ash's hat with him when he is missing during a blizzard, and continues to hold it for as long as he looks for the owner, frantically hoping to find it.
When a Donphan assails May, Ash tries to protect her by ordering Pikachu to use Thunderbolt, but the electrical attacks have no effect on the Pokemon Earth, so ash takes her in his arms and pushes her away from the Donphan's path, putting himself in danger of protect May. Later, Ash and May are separated from the group, and when she thinks she could be alone with Ash in the woods forever, she blushes. In the end, May loses the chance to take the ferry that would take her to the place where she would play her last race, and she begins to cry in despair. To comfort her, Ash puts his hands on her shoulders and stares intently into her eyes, proposing to go alone while he searches for her little brother. May is moved, but refuses Ash's offer and tells him that she has promised her mother to look after Max. However she recovers and suggests going to find Max and Brock. Touched, from her words Ash agrees.
As soon as May finishes talking to Drew, Ash gives her an ice cream, telling her he thought he wanted a dessert. This shows the care Ash has for May, and it could even be that he wanted to do something for her, because he was jealous of Drew.
Jirachi Wish Maker
May sings to Max the lullaby that their mother used to sing for them. While doing this, Ash stares at her and smiles. On one of the nights in which May folds a tongue on the star of desires he looks towards Ash very anxious; this could imply that May's desire involves Ash.
Ash gets angry when a boy named Tory Lund makes him fall to the ground and tries to beat him (he had previously lost a fight because of Tory) but May throws herself on him, putting her hands on his shoulders begging him to calm down. Ash is surprised, but quickly calms down.
Lucario and the Mystery of Mew
During the dance party, in which both take part Ash is forced to sit on the throne while May dances with another man and Ash looks jealous. Moreover, the man is much older and taller than May and Ash which may have bothered him further. When the group has to recover their Pokemon from Mew, Ash is very worried about Pikachu, and May approaches him and tries to reassure him, but he can't and seems surprised. When Ash got angry with Lucario, May immediately joined him in the lake and squeezed his arm, trying to stop him from getting into trouble. Later, May tells Ash to dry off before catching a cold, showing concern for him.
Pokémon Ranger and the Temple of the Sea
Ash and May go swimming and are surrounded by a pack of Luvdisc, the Pokémon that symbolizes love and they start swimming between them. It is said that every couple that meets this Pokémon is destined to have a loving relationship that will never end. The Manaphy who identified May as his mother seems to be sympathetic to Ash at certain times, and certainly prefers him to Jack Walker, so Manaphy may have chosen Ash as his "father" because of May's feelings. Jackie Walker declares that it is Ash, the one with the major bond with May, outclassing her brother, and asks him to separate May and Manaphy, since the latter must be free in nature. When Manaphy disappears, May begins to sob, with a broken heart, and Ash looks at her with a pained expression and shining eyes. When Jack enters the Temple, Ash warns him that it is too dangerous. However, when May returns to the Temple to follow Manaphy, Ash instinctively chases her, presumably because he can't stand being in danger.
While Samiya's temple is flooded by water, Ash puts May, Pikachu and Manaphy in a rescue capsule, to allow them to survive in the event that his plan to replace halting inaction fails. Anguished, May calls Ash with eyes full of tears, but he only asks her to stay safe in there, and in turn seems very upset. May continues to pray for Ash's safety and is almost brought to tears by the thought that he may not return; Manaphy then puts May's heart in contact with Ash's by using his powers and thanks to this drowning Ash recovers and replaces the crystal, saving Samiya. After the temple re-emerged, May left the capsule, initially thrilled that the temple was saved, acknowledging that it was thanks to Ash. His happiness, however, is quickly replaced by the sadness and fear that Ash will not return. When she sees him again, she is very happy.
May decides she wants to continue traveling with Ash, and after the end of their trip to Hoenn joins him in Pallet Town, not knowing that there are Pokemon Contest in Kanto too. This implies that she put the possibility of being with Ash before her dream. When May shows up at their home, Delia Ash 's mother recognizes her immediately, even though she has never seen her before. This implies that Ash has talked her to May a lot. When May finds out that Max had her own idea, she looks surprised, and angry, a sign that she probably wanted to travel with Ash alone, and Max messed up her plans again.
When May takes the stage for her first contest in Kanto, Ash is the only one of her three travel companions to incite her. Ash always seems to be emotionally involved and always helps May in her contests. Although he unconditionally supports all his friends, Ash seems to take May's contests much more at heart than he will with Dawn's (except when the latter is eliminated twice in succession in the preliminary round, but this probably derives from the displeasure for the bad figure made by the friend).
When May hears the sounds produced by the Pokémon Ghost, she gets scared and goes to Ash and tries to wake him, although Brock can be woken up just as easily, May doesn't even try. This implies once again that when he is afraid, May always wants Ash to reassure her and protect her.
May falls from a bridge but manages to hold on. Once again he asks for help only to Ash, even though Brock is there too. Ash rescues both her and Max, helped by Brock, but only shouts May's name, and she just thanks him.
On one occasion James tells Ash that they were helping his girlfriend (May) for the contest. It is worth noting that Ash does not deny that May is his girlfriend, while when James made such a comment about Misty, Ash vehemently denied. When the group camps, May goes to look for water and Ash, instead of finding something else to do or helping Max look for firewood, offers to help May with a gentle tone he rarely uses.
While May worries about her next competition, Ash immediately volunteers to help her train. May looks at him gratefully and thanks him. After being pissed off by Harley, May quickly asks Ash for training. After May can barely get past the first round of the competition, Ash stares at her with a lot of air and says "You deserve it. You've really changed your mind, May."
Like the rest of the group, May is upset when Ash is possessed by the ghost of the king of Pokelantis. When Ash is released, he tells May, Brock and Max, "You guys are the best." May replies, "Ash, if you keep talking like this, I'll blush."
Ash and May participate in the same contest and draw; there is only a bow (the prize for those who win contests). The two look into each other's eyes, nod, and Ash tells his Sceptile to use the Leaf Blade to split the tape in half. This shows that, Ash and May do not need to talk to know what the other is thinking, given the strength of their bond.
When May announces that she wants to follow her rivals to Johto, while Ash intends to go to Sinnoh, Max runs away sad, because he will have to separate from Ash and Brock, and he doesn't understand why his sister has decided so, given how good they are together Ash and May. In the end Ash, manages to console him and accompanies the two brothers to take the ferry. This implies that Ash wanted to avoid a difficult task for May, and that he understands that the time has come for her to do without his guidance.
May goes to visit Ash, Brock in Sinnoh. In the evening, Ash and May draw their halves of the ribbon they split and put it together again. May says the ribbon reminds her of the encouragement she received from Ash and how watching the tape cheered her numerous times in Johto.
Before May leaves to return to Johto, she and the rest of the group exchange greetings. She and Ash talk last, and each of them tells the other to do their best to make their dreams come true. When May speaks with Ash she puts her hand on her heart, and both have eyes that shine.
Before Ash left for the Unova region, you can see that he put the ornament that May gave him when she went to visit him in Sinnoh on his desk. This implies that the gift pleases him and that he is happy to have a memory of May, or would certainly not keep it so in plain sight.
After his trip to Kalos, Ash dedicates an affectionate thought to May, as he does with all his former travel companions.
AdvanceShipping is one of the most popular ships in the Pokémon fandom, and one of the three most popular ships between Ash and one of his travel companions.. Already in the first episode, May wants Ash to accompany her to the next city and the two will continue to travel together for two regions. Between the two there is a mentor-student relationship, and the two quickly bind thanks to the fact that they have similar personalities. They show in many occasions to keep one another. Because of the Mega form Blaziken, a few fans presumed that May would have returned in the XYZ anime series to Mega evolve hers, but she didn't. The theory could of been connected to fans who are hoping that Ash and May would one day cross paths with each other, again.
It rivals with PokéShipping (Ash x Misty), ContestShipping (Drew x May) PearlShipping (Ash x Dawn), NegaiShipping (Ash x Iris), AmourShipping (Ash x Serena), AlohaShipping (Ash x Mallow), AureliaShipping (Ash x Lillie), and BlueAngelShipping (Ash x Lana).