In 1639 Lord Herbert entered a second time into the matrimonial state, a prudential step as he was then situated, at the age of 38, having a young family without any sufficient guardian. He married the Lady Margaret, second daughter and co-heir of Henry O’Brien, Earl of Thomond; by which alliance he obtained some possessions, as well as a connexion with many of the best and most powerful families in Ireland. Of this, as of his first marriage, no particulars have been preserved, not even their date, or where celebrated; yet considering that both occurred during his father’s lifetime and greatest prosperity, we can readily believe that they were accompanied with all the usual demonstrations of joy, ceremony and feasting. They had but one daughter, Mary, who died during her infancy. In a family group, painted by Hanneman, a close imitator of Vandyck, Lord Herbert is represented as a Roman general, seated by his lady attired in a modern costume of pale blue satin, with their child standing before her in a reclining position. He has a very aged appearance, although one might presume that the portrait was executed when he was under forty-five. It is a very thinly and sketchily painted performance. His Lordship presents a singular appearance in a toga and tight fitting hose of deep scarlet, an ornamented leathern jerkin, and wearing a wig streaming over his breast and shoulders, sitting in a chair with his right hand resting on a walking stick, while his left hangs negligently over the arm of the chair in proximity with a mighty sheathed sword. His lady in ample folds of silk, with the usual long, tightly fitting, jewelled stomacher, has her hair in a fringe of small curls over her forehead, combed closely back, where it terminates in a knot from which a few ringlets flow behind; she wears also pearl ear-drops and a pearl necklace, which ornaments are repeated on her child. The same year, on the 8th of April, he lost his mother, Anne, Countess of Worcester, who was buried at Raglan. It is possible, therefore, that his marriage was deferred during her illness, and not celebrated until some months after her decease. It was then the 15th year of Charles the First’s reign. Before the close of the year following, the Long Parliament commenced its sittings, when Lenthall was chosen Speaker. All projectors and monopolists were denounced as incapable of holding office, several members, therefore, withdrew, whose places were speedily supplied. What must have been his Lordship’s impressions under the existing aspect of political affairs may easily be conceived, while as yet “Royalist” and “Roundhead” could scarcely be called popular terms of party distinction.