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Michelle, Katie and Helena become available to date once Flint County, Whetstone and San Fierro are unlocked (although Helena is first encountered in Red County, which is accessible from the start of the game, she does not appear until the second region is unlocked).
Barbara becomes available once Tierra Robada, Bone County and Las Venturas are unlocked.
While some are necessary to complete missions, each girl comes with a variety of perks and benefits.
Dating any of the six girlfriends is not required for 100% Completion, with the exception of Millie Perkins (although Millie can be killed during her first date).
Quests through the source code of the game also reveal various hidden button codes for special cheats, yet the button combinations are up to the point of writing unknown.