Cait's first memories of Jack involve him crutching by her as a bald Plebe (Freshman) and her yelling what she hoped would be an encouraging "You got this Sylvester!" Jack's first memories are of a very persistent girl in need of Chem tutoring who laughed much too hard at his jokes. After much hemming and hawing, he finally agreed to move to 6th Company for her and the rest is history.

Jack & Cait got engaged at Eden Gardens State Park near Destin, Florida. After too many glasses of wine the night before, Jack tucked Cait into bed as she expressed her worries about never getting engaged. Little did she know, Jack then went right downstairs with the ring to plan the proposal for the very next day. After walking through the gardens while Jack made small talk about the moss growing from the trees, he finally got down on one knee to squeak out a "Will you marry me?"

Jack and Cait got legally married at the Santee Courthouse outside of San Diego, California with their parents and witness Gordon Livermore. This just makes for lots of dates that they can celebrate their marriage!