Man, Kenny's love life is one of those South Park mysteries that never gets fully explored, but there are hints here and there. In earlier seasons, especially around the 'Kenny Dies' arc, there’s a subtle suggestion that maybe Karen, his little sister, is his closest emotional connection—but obviously, that’s familial. Later episodes like 'Tweek x Craig' play with shipping culture, but Kenny’s mostly just chaotic neutral in romance. The show’s more focused on his absurd deaths or his family’s poverty than his dating life. Though, in 'The Poor Kid,' he briefly bonds with a girl at foster care, but it’s more tragic than romantic. Honestly, if Kenny had a girlfriend, she’d probably die in some bizarre way too—it’s his brand.
That said, fan theories go wild. Some folks speculate his muffled voice hides secret relationships, or that his 'immortal' reboot in later seasons resets his love life. But canonically? Nah. Kenny’s forever the weird, tragic third wheel in the group, and that’s kinda perfect for him.