Xoxo
Origin
From use of X/x to mean “kiss†and O/o to mean “hugâ€. Use of “X†to indicate a kiss attested since 1763,
OED: “Xâ€
1763 Gilbert White Letter (1901) I. vii. 132, I am with many a xxxxxxx and many a Pater noster and Ave Maria, Gil. White.
Online Etymology Dictionary|X
preceded by medieval use of “Xâ€, which was then kissed, by illiterates to indicate a signature.
How Stuff Works: How Valentine's Day Works
Use of “O†is more recent, and presumably created by analogy (e.g., X/O in tic-tac-toe). Speculative theories on precise origins abound.