Constantly together, Jessie and James are a part of Team Rocket and are on an assignment from their boss Giovanni to capture Ash's Pikachu. Some see their relationship as a deep friendship or partnership that could never be broken, but some see it more than that. Behind the "evil" that is Team Rocket, these two can be seen as a romantic couple, though it has never blatantly been stated. Whether apparent or not, they have had an interesting past and there are several instances that can be clues to a more meaningful and possible romantic relationship.

Their meeting has been changed recently due to a Pokémon Chronicle episode, "Training Daze". In regards to this episode, they met each other in a Team Rocket training session. In the original story, the two had dropped out of Pokémon Tech together and later joined the Sunny Town bicycle gang, as explained in "The Bridge Bike Gang". It could be said that they reunited when joining Team Rocket in "Training Daze" but just by observation this is unclear, as they made no mention of knowing each other from the past.

The two have had a difficult past. With Jessie losing her mother at such an early age, she had to raise herself most of her young life while in a foster home. Her teenage years consisted of constant let downs – As she failed trying to become a Pokémon nurse and dropping out of Pokémon Tech. James had a rich and fruitful life, but he was constantly interrogated by a woman named Jessiebelle, whom he was later to be married to when he became of age. He ran away as a young child to get away from the hardships his family had to offer and eventually enrolled in Pokémon Tech. There the two met each other, but flunked out to do "frolicking" the entire night before final exams. Jessie and James seemed to have met each other at exactly the right time in their lives - They both needed someone to depend on and a shoulder to cry on. This made them a perfect match for each other and their relationship could only grow from there.

There are many situations that can lead to clues about romantic feelings between Jessie and James. One of the episodes that these fans, known commonly as RocketShippers, see as the most evident is "Holy Matrimony", when James visits his home thinking his parents have died. He is met up by his fiancé Jessiebelle whom he must marry in order to receive his inheritance money. Jessie and Meowth are both very interested in the money - Jessie even tells Ash, Misty and Brock that they were going to fake the wedding just to run off with the money. Jessie and Meowth make a plan to do just that but things take a turn for the worse when Jessiebelle captures James and her Vileplume Stun Spores the group. It was only after Jessie was forced to leave that she began to worry for James, since she knew that things were out of her hands and that he could actually be forced to marry Jessiebelle. At the end of the episode Jessie and Meowth assume that James decided to marry and she is obviously very upset by this. But to her surprise, James appears in their trademark Meowth hot air balloon and pulls her up into the balloon's basket. The two reconcile, as Jessie explains that their freedom is more important than getting the money he's inherited. The scene ends with them looking at each other, hand in hand, with the balloon floating off into the horizon. This episode proves that the two find freedom within each other and it also shows that even money won't set the two apart.

An episode that proves their devotion to each other the most is in the Pokémon Chronicle special, "Training Daze". Jessie sees all of her past partners as unfit and never able fulfill her needs in what she wants in a teammate. But when James comes along, he promises that he will not let her down. The two seem to take an instant liking for each other - Jessie appreciates the fact that she is finally matched up with a strong-willed partner and James wants to fulfill that need. In their early days, the two were very serious about their work and looked straightforward on the mission - Jessie even willingly puts her life on the line to cross a broken down bridge to make sure it's safe. But at such an early stage in their relationship, they also seem to care immensely for each other. When the bridge breaks as James crosses it, she is obviously considered of his safety and tells him not to let go. James apologizes and allows himself to fall, as Jessie screams out his name. He's extremely wounded and seems as if he is unable to participate any longer in their training. Jessie visits him in the hospital and upon their final test, she begins to break down, venting how everyone leaves her and that it's always just her in the end - Only by losing James was her breaking point. But when he returns unexpectedly, he tells her that he's kept his word and that he will never let her down, even when he is hurt. She is so heart-stricken by his words that she begins to cry, but quickly wipes away her tears and focuses herself on the mission. They later find themselves in the same predicament as before, with James about to fall down a very deep hole. He lets go, just as he did previously, but this time Jessie catches him and pulls him back up to safety. Even way back in their first days of trainings the two have recognized the fact that they need each other.

Jessie and James are very passionate about style and their appearance. The two enjoy taking part in elaborate uniforms as well as the art of cross-dressing, where Jessie will dress up as the male and James will be the female. They even designed their own uniforms "to reflect [their] free spirit!" and their "sense of stylish good taste", as stated in "Due's and Don'ts". In "Bad to the Bone", James explained to Meowth: "Jessie and I have worn lots of disguises and we share a certain sense of style. Even under all those veils I'd recognize that fashion flare anywhere!"

The pair have an undeniable understanding for each other – To the point where they can cite their motto, and even different variations of it, in perfect and flowing harmony. When scared or just plain out of excitement, Jessie and James will throw themselves into each other's arms. Either seen as romantic or not, it's truly evident that Jessie and James depend and support each other and have seen each other through thick and thin.