In December 1593 it was said the "young Earl of Bedford was paying his addresses to Mrs Bridges, the lord Chandos' heir." At court in the 1590s, she obtained money from Charles Lister of New Windsor (d. 1613) and promised to marry him, and he complained in 1598 that he had loaned her more than £3000 and bankrupted himself. Brydges invested £150 of Lister's money in the Earl of Essex's assault on Cadiz. Around this time Brydges may have had some kind of affair with Essex, possibly to be identified as the woman noted by Rowland Whyte as "his fairest B."