Team Rocket's Jessie and James are two of the Pokémon series' most famous characters, attempting episode after episode to steal Ash's Pokémon with easily foiled schemes. The duo are partners under Team Rocket's command, but fans often wonder if there's something more to their relationship, whether they're secretly in love or outwardly dating.
Jessie and James first appeared in the Pokémon anime's second episode, Pokémon Emergency. Since then, they've hounded Ash and his friends throughout Pokémon's world, endearing themselves to fans with their antics. In the show's fiction, the two met at the Team Rocket Academy, where they formed a team with Meowth and pledged to stay by each other's sides.
According to Bulbapedia, the first big piece of evidence of Jessie and James' couple-hood the so-called RocketShipper community discovered was an untranslated version of the official but highly controversial Pokémon: The Electric Tale of Pikachu manga. The manga - which also features several instances of heavily sexualized characters, including Misty, who is canonically only 10 years old - ends with an epilogue that shows James confessing his love to Jessie, followed by an image of an apparently pregnant Jessie, James hugging her from behind and lovingly resting his chin atop her head. The manga is a self-contained retelling of the original anime series and not part of the show's official canon, however, so this is considered little more than the author's interpretation of Jessie and James' relationship. Whether they have feelings for each other in the anime series is less explicit.
Are Pokémon's Jessie & James A Couple In The Anime?
Unlike The Electric Tale of Pikachu, the Pokémon anime never shows Jessie or James outwardly expressing romantic love for one another. Despite this, fans point to several episodes with hints they're in love: Training Daze! depicts the team's origin story as described above and includes a scene in which James accidentally falls on top of Jessie, causing her to blush. At the end of Holy Matrimony!, Jessie is distraught because she believes James has decided to marry his arranged fiancee Jessebelle (who happens to look almost exactly like her). He suddenly appears, having rejected the marriage and his inheritance in favor of staying with the team, and he and Jessie share a prolonged handshake as they gaze into each other's eyes. And in the Japanese-language version of A Fork in The Road! A Parting of The Ways!, a character seems to be asking James if he and Jessie are more than friends, before he interrupts with what Bulbapedia calls "an affirmative grunt."
These are but a few of the most convincing examples of Jessie and James' supposed relationship, but they still don't confirm the two are a romantic couple - and fans don't even know for sure what the duo's sexual orientations are, for that matter. The supposed evidence could simply mean Jessie and James share a strong friendship as a result of being similarly goofy teammates in a world full of people quite unlike them. In any case, plenty more hints can be found on the Bulbapedia RocketShipping page, but fans hoping for more definitive evidence will have to hope and wait.
Update: Twitter user @RocketTRIOlove, a Team Rocket fan account, pointed Screen Rant to a Buzzfeed Japan interview with the Japanese voice actors for Jessie, James, and Meowth (translation via Pokémon fan site Dogasu's Backpack). When asked if Jessie and James would ever be a couple, the actors agreed it could never happen, and Meowth voice actor Inuko Inuyama said, "If the two of them were involved with each other romantically, then they wouldn't have been able to work together in [Team Rocket] all this time." While this isn't an official answer from The Pokémon Company - just a subjective interpretation from the characters' actors - it does at least lend insight into how some of the show's creators see Jessie and James' relationship.
Source: Bulbapedia