Pokémon is a franchise with a long and detailed history and a fandom that spans generations. It offers something for everyone, from games to anime to manga. As with most things, shipping is a huge part of the Pokemon fandom. This list will focus solely on shipping in the anime. Heads up, trainers; the ships listed below are ranked purely on fandom reactions and support.
Everyone is entitled to their own opinions and ships, and no one deserves to be bullied based on the fictional characters they pair. Remember to treat fellow members of the fandom with respect, and good luck on your Pokémon journey.
10 WORST: May And Harley (CookieShipping)
Harley is one of May’s Pokémon Contest rivals, and, as such, occasionally gets shipped with her. However, many fans do not like this ship. Harley has rarely been genuinely nice to May. He’s manipulative and isn’t above cheating to get a win over her in contests. He’s not respectful toward May; he’s vindictive. He hates May because she looks like a girl who ate his food when he was a child, and, once May starts winning contests, he wants to make her pay for all of the times she has defeated him. He even enlists Team Rocket’s help to prevent May from getting the last ribbon she needs to enter the Grand Festival. Best to leave this ship alone; like Harley, it has far too many thorns.
9 BEST: Professor Burnet And Professor Kukui
Professor Burnet and Professor Kukui are a cute pairing that exists in both the games and in the anime. In the games, they’re already married, but in the anime, they aren’t. The anime gave fans the treat of seeing these two before their marriage, allowing viewers to watch their relationship grow and blossom. The two complement each other well, both in personality and in their love of Pokémon. When Kukui pulled out the Pokéball holding an engagement ring and said “I choose you” to Burnet, it was a great wrap on such a wholesome and cute relationship.
8 WORST: Ash And Iris (NegaiShipping)
Ash and Iris is the least popular of the Pokémon ships involving Ash and his female traveling companion. Most fans claim it’s because they don’t like Iris’ attitude or how she treats Ash; she often argues with him and tends to call him a kid. Their interactions and relationship is more like bickering siblings or rivals than romantic.
That doesn’t mean that Iris is terrible or deserves any of the hate that she tends to get. She’s a cool and strong dragon trainer who serves as a better friend to Ash than anything more.
7 BEST: May And Drew (ContestShipping)
May and Drew started as Pokémon Contest rivals. At first, Drew was rude and critical of May’s skills as a contest trainer, which often affected May’s confidence and left her annoyed at Drew. However, the two’s relationship changed as the series progressed. Drew always gave May a rose whenever he saw her. Initially, he said it was for May’s Beautifly, but eventually, he admitted the rose was for her. May and Drew’s attitudes toward each other grew softer and more caring, until others, including May’s mom, thought that the two were dating. May eventually leaves Ash’s party to follow Drew and participate in Johto contests.
6 WORST: Dawn And Paul (IkariShipping)
This one is the classic “the good girl and the bad boy” ship, and it is somewhat popular in the Pokémon fandom. However, it’s extremely hard to like for some fans, mainly because of Paul's attitude. There’s a bad boy, and then, there’s an outright jerk, which Paul easily fits. He can’t be bothered to remember Dawn’s name, and all of his interactions with her are negative and lacking in chemistry or dynamic. Love/hate relationships have their place, but save Dawn the trouble of this bad boy and ship her with someone more worthy of her time, such as Zoey or Barry.
5 BEST: Ash And Misty (PokeShipping)
PokeShipping is one of the oldest ships in the Pokémon fandom, and it is one of the most popular. Misty has traveled with Ash throughout Kanto, the Orange Islands, and Johto, and she has visited Ash in Hoenn and Alola. The 4KIDS English dub heavily pushed the possibility of a romantic relationship between these two. "Misty’s Song", a song featured on the 2.B.A. Master soundtrack, has Misty singing about how she loves Ash.
Misty often gets jealous when other girls flirt with Ash, and, while Ash never expresses his feelings, he does get jealous when other guys flirt with Misty. Misty may have initially traveled with Ash because he destroyed her bike, but she stuck with him long after that bike was fixed.
4 WORST: Ash And Jessie (RedShipping)
This is a smaller ship that pairs Ash with Jessie, a member of Team Rocket. It has its supporters, but a larger majority are against it. One of the major reasons against this ship is the age difference between Ash and Jessie. Ash is a 10-year-old trainer, while Jessie is a grown woman. Jessie also does not care about Ash. She stalks him around the Pokémon world, battles him numerous times, insults him by constantly calling him ‘twerp’, and, on a few occasions, has even tried to kill him. Her motives for following Ash revolve solely around his Pikachu, which she wants to capture due to its incredible power. It’s best to send this ship blasting off again.
3 BEST: Ash And Serena (AmourShipping)
Ash and Serena is another extremely popular ship in the Pokémon fandom. Serena’s crush on Ash is confirmed in canon. It’s why she goes to find him, although she tries to hide it by saying she wanted to return his handkerchief. Ash and Serena met at Professor Oak’s Summer Camp when Ash helped a lost and injured Serena.
Unlike previous traveling companions, Ash actually invites Serena to accompany him on his journey. He also compliments her when she changes her hair and outfit. At the end of the Kalos series, Serena tells Ash that she’s going to get better for him. She kisses him, making her the only female companion to do so. This kiss sent shockwaves throughout the Pokémon fandom.
2 WORST: Ash And Pikachu (PikaShipping)
The Pokémon shipping fandom is quite diverse. There are Human x Human ships, Pokémon x Pokémon ships, and, finally, Human x Pokémon ships. Shipping Ash with his first Pokémon, Pikachu, is the most popular of these human/Pokémon ships. Ash and Pikachu have been inseparable since the very first episode, and they have gone on many adventures. Some viewers have taken the pair's relationship to the next level, making Ash and Pikachu's interactions romantic. This has sparked debate from those who oppose this ship and prefer to keep Ash and Pikachu’s relationship platonic. There's something weird about seeing Ash romantically involved with Pikachu, his best friend. This controversy has lasted seasons, and it shows no sign of slowing down.
1 BEST: Jessie And James (RocketShipping)
Prepare for trouble, and make it double. RocketShipping is one of the oldest ships in the Pokémon anime fandom. Ever since Jessie and James first appeared with their catchy motto and wide array of disguises, these two have an undeniable chemistry that made fans ship them. Jessie and James support each other and have no problem with physical contact, often hugging and holding each other at least once an episode. However, the biggest confirmation for the pair is in the epilogue of a manga based on the anime, The Electric Tale of Pikachu, where Jessie and James marry. While it’s uncertain on whether or not the anime will ever confirm this ship, RocketShipping remains as popular as the Team Rocket motto.