Dion sojourned in the Upper Town of Athens, with Callippus, one of his acquaintance; but for his pleasure he bought a seat in the country, which afterwards, when he went into Sicily, he gave to Speusippus, who had been his most frequent companion while he was at Athens, Plato so arranging it, with the hope that Dion's austere temper might be softened by agreeable company, with an occasional mixture of seasonable mirth. For Speusippus was of the character to afford him this; we find him spoken of in Timon's Silli, as "good at a jest." And Plato himself, as it happened, being called upon to furnish a chorus of boys, Dion took upon him the ordering and management of it, and defrayed the whole expense, Plato giving him this opportunity to oblige the Athenians, which was likely to procure his friend more kindness than himself credit. Dion went also to see several other cities, visiting the noblest and most statesmanlike persons in Greece, and joining in their recreations and entertainments in their times of festival. In all which, no sort of vulgar ignorance, or tyrannic assumption, or luxuriousness was remarked in him; but, on the contrary, a great deal of temperance, generosity, and courage, and a well-becoming taste for reasoning and philosophic discourses. By which means he gained the love and admiration of all men, and in many cities had public honours decreed him; the Lacedaemonians making him a citizen of Sparta, without regard to the displeasure of Dionysius, though at that time he was aiding them in their wars against the Thebans.
It is related that once, upon invitation, he went to pay a visit to Ptoeodorus, the Megarian, a man, it would seem, of wealth and importance; and when, on account of the concourse of people about his door, and the press of business, it was very troublesome and difficult to get access to him, turning about to his friends, who seemed concerned and angry at it, "What reason," said he, "have we to blame Ptoeodorus, when we ourselves used to do no better when we were at Syracuse?"After some little time, Dionysius, envying Dion, and jealous of the favour and interest he had among the Grecians, put a stop upon his incomes, and no longer sent him his revenues, making his own commissioners trustees of the estate. But, endeavouring to obviate the ill-will and discredit which, upon Plato's account, might accrue to him among the philosophers, he collected in his court many reputed learned men; and ambitiously desiring to surpass them in their debates, he was forced to make use, often incorrectly, of arguments he had picked up from Plato. And now he wished for his company again, repenting he had not made better use of it when he had it, and had given no greater heed to his admirable lessons. Like a tyrant, therefore, inconsiderate in his desires, headstrong and violent in whatever he took a will to, on a sudden he was eagerly set on the design of recalling him, and left no stone unturned, but addressed himself to Archytas, the Pythagorean (his acquaintance and friendly relations with whom owed their origin to Plato), and persuaded him to stand as surety for his engagements, and to request Plato to revisit Sicily.
Archytas, therefore, sent Archedemus and Dionysius, some galleys, with divers friends, to entreat his return; moreover, he wrote to himself expressly and in plain terms, that Dion must never look for any favour or kindness if Plato would not be prevailed with to come into Sicily; but if Plato as often declined, Aristippus, the Cyrenaean, then present, said that received letters full of solicitations from his sister and his wife, urging him to beg Plato to gratify Dionysius in this request, and not give him an excuse for further ill-doing. So that, as Plato says to himself, the third time he set sail for the Strait of Scylla-"Venturing again Charybdis's dangerous gulf."This arrival brought great joy to Dionysius, and no less hopes to the Sicilians, who were earnest in their prayers and good wishes that Plato might get the better of Philistus, and philosophy triumph over tyranny. Neither was he unbefriended by the women, who studied to oblige him; and he had with Dionysius that peculiar credit which no man else ever obtained, namely, liberty to come into his presence without being examined or searched. When he would have given him a considerable sum of money, and, on several repeated occasions, made fresh offers, which Plato did come Dion should be assured of whatever he desired. Dion also Dionysius was very safe in his munificence, he gave little to those who were ready to take all they could get, and a great deal to Plato, who would accept of nothing.