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The earliest surviving letters date to 1847 and contain descriptions of Jack’s adventures at sea and Jeanie’s activities in New York and Devasego. From the letters, we learn that towards the end of 1852, Jack and Jeanie confessed their feelings for one another, and the letters reveal the depth of their relationship.
1853 March 11 –Jack to Jeanie - Highlights include an account of a “stormy talk” with his father about his engagement and the uncertainty of his future career choices once he left the navy.
1853 March 13 – Jeanie to Jack - The former encourages Jack to reconcile with his father, and says that Commodore Wilkes claimed to love her “almost as much as his own daughters.”
1853 May 21 – Jack to Jeanie - The quarrel between father and son is past, but “forgotten it never will be." Jack expresses his concerns about her living in the South.
1853 May 23 – Jeanie to Jack - “I think of you always.” Also, Jeanie shares her opinion regarding Jack's future professional prospects.
1853 June 1 – Jack to Jeanie - tells how he helped fight a house fire, recalls grief at losing his mother
1853 June 2 – Jeanie to Jack - Jack’s prospects in “Carolina,” flirtatious talk about eating strawberries