Caroline likely attended the Burwell School in the early 1840s. She was Mrs. Burwell's first boarder at the school and consequently held a special place in her heart. The feeling was most likely mutual. Caroline Cowan may have regarded the Burwell School as a second home. Mrs. Burwell (Margaret Anna Robertson) wrote affectionately of Caroline in her letter to her daughter Frances Armistead Burwell on 25 January 1856:
"I had a long affectionate letter from Vene Cole the other day & one from Cuddy Green (Cowan that was). She was the first boarder I ever had, was a little child when she lived here. She has now three children & they say her husband is killing himself drinking. She sent me a beautiful embroidered white crape scarf--much too youthful for me. Nan will have it. I valued the expression of kind feeling--how such little affectionate attentions sweeten life."
Caroline Cowan's marriage announcement to James G. Green was listed in The Hillsborough Recorder  on 19 April 1848. It was unusual to publish notices of student marriages in the Recorder, in this case, it may have indicated that Caroline had a special place in the Burwell family. Eight years later, she was still writing affectionate letters to Mrs. Burwell and sending her Christmas gifts .
Caroline was called Cuddy.