From History: ~1.75 billion years ago (+/- 50 million)
Last Eukaryote Common Ancestor
By 1.75 billion years ago, sexual reproduction emerged. It emerged after viruses and bacteria deep in early single-celled eukaryotic history, before the major branches of life split apart. Early sexual systems were often not male/female, but mating types. Sometimes 2, 3, or even dozens. In rare cases, thousands.