Jamie fell in love with Annalise de Marillac while studying in Paris, even writing his sister and father of her.

He described himself as lovesick in the truest sense of the word, saying he "went about in a daze, tripping over my feet. Waited in the street, in hopes of seeing her come out of her house to the carriage."

After noticing Annalise was paying particular attention to Charles Gauloise, Jamie challenged the other man to a duel. Though Jamie technically won the duel, Annalise married Charles a month later.

Jamie returned to Scotland despondent, and briefly contemplated becoming a monk. He was still somewhat in love with Annalise a year later, when he returned to France to fight as a mercenary soldier. However, their paths did not cross.

He and Annalise saw each other again three years later at Louis's court. Though Annalise lightly flirted with him and called him "my little savage," Jamie was only interested in Claire.