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No, although there is a scene in "Bad to the Bone" where he remembers them cross-dressing where she is kneeling down and holding his hand like she's about to kiss it. James has told Jessie at least once that he loves her, but this was most likely meant as a friend, since he said "you guys" to include Meowth. They also have an agreement that if they die they'll find each other in the afterlife.

In the Pokemon graphic novel series they get married at the end, and Jessie is pregnant with their first child.

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Q: Did Jessie ever kiss James in Pokemon?
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