At Least Ten Characters

The Gwendoline form may introduce pronunciation confusion -- does that last syllable rhyme with wine or win or when? We vote Gwendolen as not only the most proper but the clearest spelling, followed by Gwendolyn, with Gwendoline a distant third.

Jacqueline originated as a feminine form of Jacques, the French variation of James, and therefore Jacob. Jacob was ultimately derived from the Hebrew name Ya’aqov, and gets its meaning, "supplanter" from the story of Jacob supplanting his brother Esau as the first-born son in the Bible. Jacqueline was first used in France in the Middle Ages.