Jim and Phoebe met by seeing each other everywhere while out on their errands and eventually he decided to ask Phoebe out on a date, despite being slightly bemused when she misunderstood the pretty obvious meaning of a remark he made. On the date, Jim fell away from his initially polite and friendly demeanor and, seemingly just to amuse himself, started making highly inappropriate comments which Phoebe found disturbing.
He claimed that he wrote "erotic novels for children" which were "wildly unpopular". He also said that he had a PhD which for him stands for (looking down at his crotch) "pretty huge d..." (cut by Phoebe).
Phoebe later referred to him as the "rude guy".