Ranking Ash's Romantic Interests: From Least to Most Beloved

Throughout the Pokémon anime series, Ash has journeyed alongside various girls, with some of them developing feelings for him along the way. While fans may immediately remember the first companion they saw with Ash, it raises the intriguing question: which companion is truly the best match for Ash?

When looking at the key female characters in the Pokémon anime, it becomes clear which girls had the strongest connections with Ash. Although Ash may not have reciprocated the same level of interest, these girls have been more vocal about their feelings towards him, which plays a significant role in determining the rankings. While some relationships may have romantic undertones, all of them ultimately contribute to Ash's closest friendships.

May - Ash's Good Friend

Appears in Pokémon: Advanced Generation

Pokemon's May smiling in front of some trees. - Appears in Pokémon: Advanced Generation - May - Ash's Good Friend

May was Ash's travel partner in the third-generation series. Originally from the Hoenn region, she had little knowledge of Pokémon before meeting Ash. He served as a mentor to May, teaching her about battles, Pokémon, and how to take care of them. May later became a Coordinator, a trainer who competes in Pokémon Contests.

May has not appeared much in the Pokémon anime since the Advanced Generation series because her original voice actress, KAORI, lost her voice.

Lillie - Looking Up to Ash

Lillie admires Ash as a role model and looks up to him for inspiration. Despite their differing goals and interests, Lillie values their strong friendship and is always willing to support Ash. In contrast to Misty, who showed romantic interest in Ash, Lillie's focus is on learning and growing as a trainer. Though she may not have as many appearances as other characters, Lillie's admiration for Ash shines through in their interactions.

Appears in Pokémon Sun & Moon

Lillie hugging Snowy the Alolan Vulpix in the Pokémon anime. - Appears in Pokémon Sun & Moon - Lillie - Looking Up to Ash

Lillie, a member of Ash's Pokémon School class, is based on the character from the Sun and Moon video games. She is the daughter of Lusamine and played a significant role in the Sun & Moon storyline. Initially, Lillie was terrified of Pokémon when she met Ash. With Ash's help, she overcame her fear and eventually obtained her own Pokémon, an Alolan Vulpix named Snowy. Through Ash's guidance, Lillie developed into a skilled Pokémon trainer and gained confidence in her battling abilities.

Dawn - Like a Sister

It's difficult to determine if Lillie has romantic feelings for Ash, which is why she is ranked lower. However, it is evident that she greatly admires him. It wouldn't be a shock if Lillie's feelings for Pallet Town's beloved trainer were eventually revealed.

Appears in Pokémon: Diamond & Pearl

Pokémon's Dawn Smiling on a mountainous path. - Appears in Pokémon: Diamond & Pearl - Dawn - Like a Sister

Dawn is Ash's main companion in Sinnoh, inspired by the female player character in Pokémon Diamond and Pearl. Unlike Misty and May, Dawn quickly stood out by not holding onto anger when Ash's Pikachu accidentally destroyed her bike. She had her own goal from the start: to become a great Coordinator like her mother. Because Dawn and Ash both had clear aspirations, they got along well. Sometimes, Dawn even wore a cheerleader outfit to support Ash during his gym battles.

Bianca and Ash had a special bond that went beyond friendship. They shared a kiss that sealed the deal, solidifying their connection in a romantic way. Bianca's feelings for Ash were clear, and their relationship blossomed into something more than just friends.

Appears in Pokémon Heroes: Latios & Latias

Pokémon's Bianca looks with her mouth open at Ash across the river. - Appears in Pokémon Heroes: Latios & Latias - Bianca - A Kiss to Seal the Deal

Bianca, a character unique to the fifth Pokémon film, Pokémon Heroes: Latios & Latias, is a bit tricky to understand when it comes to her feelings for Ash. Throughout the movie, she is sometimes impersonated by a Latias, who also seems to have a crush on Ash. This makes it hard to determine Bianca's true feelings. Despite this confusion, Bianca and Ash team up to protect Latias and save the city of Alto Mare from the thieves, Annie and Oakley, who were trying to take over the city's defense system.

Melody - Aggressively Interested

Bianca and Ash's bond grew stronger during their adventure. When it was time to say goodbye, Bianca hurried to the docks and surprised Ash with a kiss. Was it really Bianca, or was it Latias pretending to be her?

Appears in Pokémon the Movie 2000

Pokemon: Melody from the Movie 2000 standing in front of some rocks. - Appears in Pokémon the Movie 2000 - Melody - Aggressively Interested

In Pokémon the Movie 2000, Melody is portrayed as the festival maiden from the Orange Islands. Despite her rebellious nature, she eventually warms up to Ash after giving him a "traditional" welcome kiss. This causes tension with Misty, as they both share an interest in Ash but don't openly admit it.

Melody makes a brief appearance in The Rise of Darkrai, appearing in a montage of other movie moments. She shows her bravery by helping Ash fulfill a prophecy and save the day after discovering the legends of her home were true. Melody openly expresses her interest in Ash and even points out Misty's feelings for him, positioning herself as a rival. Unfortunately, Melody does not make another appearance.

Misty - It's Complicated

Appears in Pokémon: The Beginnings and To Be A Pokémon Master

Pokémon's Misty smiles and winks at the camera with a lens flare. - Appears in Pokémon: The Beginnings and To Be A Pokémon Master - Misty - It's Complicated

Misty, the original Poké girl, has had the most screen time among Ash's potential love interests. Throughout the series, Misty hints at having a romantic interest in Ash, although Ash's feelings are not always clear. She tends to get jealous when other girls interact with Ash, like Melody.

In the English dub of the anime, Misty's attraction to Ash was exaggerated, giving Western fans a more "childhood romance" perspective. The English soundtrack even included a song for Misty expressing her feelings for Ash, making it more obvious. Despite Misty's return for the final episodes, their relationship did not deepen significantly. Ash remained clueless about Misty's feelings, and their bond did not progress in a meaningful way.

Serena - Nearly Official

Appears in Pokémon XY

Pokemon's Serena winks in the middle of a mall. - Appears in Pokémon XY - Serena - Nearly Official

Serena and Ash's relationship dates back to before their time together in XY. They first met at a summer camp organized by Professor Oak, where Ash assisted Serena when she got hurt. Serena never forgot this act of kindness and was surprised to later realize that Ash was the same boy who had helped her in the past.

Unlike other female characters in the series, Serena was clearly meant to be Ash's love interest. Ash's positive and determined attitude inspired Serena to pursue her own dreams instead of following her mother's wishes. When Ash faced a tough defeat against gym leader Wulfric and fell into a slump, Serena stood by his side to support him.

Before parting ways, Serena gave Ash a kiss before setting off to the Hoenn region to try her hand at Pokémon Contests. Despite Ash being a bit clueless about Serena's romantic feelings, she made her affection for him clear with that kiss.

The truth is, Ash wasn't designed to be a character focused on romance. The series' pattern of resetting him in a new region meant that his relationships never had the chance to progress further.

Even though Serena may seem like Ash's top romantic interest, the reality is that Ash wasn't meant to have a love story. With Ash no longer the main character, it's unlikely he'll ever have a romantic partner on screen. Instead, he'll continue his endless Pokémon journey.

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