The newly-widowed Constance was straightaway married to Ranulf, earl of Chester, a union arranged by Henry II, who had just knighted Ranulf. The marriage appears to have been a complete disaster. Constance rebelled against her husband and schemed with Richard I, and in 1195/6 Ranulf captured Constance and imprisoned her at the caste of St. James sur Beuvron when she tried to meet up with Richard to conclude a treaty. The marriage to Ranulf was dissolved on grounds of consainguinity, and Constance took a third husband more preferable to her, Guy de Thouars, and produced two more daughters with him. Constance died in 1201, leaving Eleanor fatherless and motherless.
Her brother's conflict with their uncle John resulted in Eleanor's capture by John at Mirabeau in 1202. She was then 18. Her brother conveniently disappeared the following year, leaving Eleanor the rightful heiress of Brittany. She would live the rest of her life as John's captive.
In 1209, she was joined by Margaret and Isobel, the daughters of King William of Scotland, sent to England to live as hostages. There are some delightful records of these Scottish princesses found in the Exchequer Records, which give us some idea of their lives. We know that Margaret and Isobel had at least two governesses, as money was sent to provide robes for the princesses and their governesses. The princesses had robes of green, trimmed with rabbit's fur, and russet hoods. In June 1213, when Eleanor, Margaret, and Isobel were staying at Corfe, John ordered that the ladies be sent green robes, lambskin-trimmed cloaks, and summer slippers.
She did not spend her time locked in a dungeon or even imprisoned in a castle. Eleanor accompanied John to Aquitaine and Poitou in 1214, as a pawn in his schemes against her half-sister, Alix. Otherwise, Eleanor divided her time between the castles of Corfe, Marlborough, Gloucester, and Bristol. She had maids to wait on her and her uncle supplied her with fabric for clothing and bedding, among other things. Eleanor seems to have been an avid horsewoman, as John gifted her a saddle and gilded reins, and her cousin Henry also sent her a saddle. She seems to have liked figs and almonds, as those were among the treats that her uncle would send her.
Although John sometimes dangled Eleanor as a matrimonial prize, he never allowed her to marry. She outlived him and died, still a captive, in 1241.