Jessebelle
Jessiebelle (Japanese: ルミカ Rumika) was the woman appointed to be James's fiancé by his parents in the Pokémon anime. Her voice actress in Japanese is 林原めぐみ Megumi Hayashibara, her English voice actress is Rachael Lillis and her Brazilian-portuguese voice actress is Isabel de Sa.
In Holy Matrimony!, James returned to his parents' mansion in Kanto after receiving word that they had died. However, this was a hoax to lure him to marry his arranged fiancé, Jessiebelle; if he did marry her, he would receive his massive inheritance. However, James was absolutely terrified of Jessiebelle; he told Jessie, Meowth, and Ash's group how the marriage had been arranged when he and Jessiebelle were very young, and she had always been bossy and annoying to him.
Since he had not seen Jessiebelle for years, James was shocked to discover that she had an almost identical appearance to Jessie. Jessiebelle expelled Jessie, Meowth, and Ash's group from the home and chased James around the mansion's basement, threatening him with her Vileplume's Stun Spore and a long whip. Eventually, James's old pet Growlithe, Growlie, came to rescue him from Jessiebelle. The two fiancés had a Pokémon battle, with Growlie being victorious and Jessiebelle running off the estate. James declined his inheritance and returned to Jessie and Meowth.
Jessiebelle is, as demonstrated by her episode appearance, extremely controlling and obsessive. She is a stuck-up, elitist woman, and her professed affection for James may be a front to get to his parents' money. Many fans see this as the reason for James now having a fear of commitment.
It should also be noted that Jessiebelle owning Vileplume may have significance, since back then it could have been considered the counterpart of Victreebel, one of which James owned.