Jeremy's relationship with Miss O'Shaughnessy was difficult from its inception in 1900, in part because of her intense God-fearing piety that would not suffer Jeremy to approach within an offensive distance, but mainly because of Josiah's outspoken disapproval. His staunch Presbyterian beliefs, fixed immovably by the short sermon he had heard on the only occasion he went to church, were offended by her family's 'elaborate and tawdry' Catholicism. In addition, and even though her parents represented the cream of Dublin society and socialised regularly with Sir William and Lady Wilde (parents to the now disgraced Oscar) he considered her to hail from an improper background: "Now't but incestuous papes and sodomites!" was his summation.

In consequence, Jeremy's first invitation for her to take tea with his parents was an occasion where all parties found it difficult to relax. It was Josiah who broke first, just as Miss O'Shaughnessy was removing her coat. "I'll have no Fenian scum in this house," he screamed to all assembled, "and no son of mine will consort with that rabid whore of Satan." So saying, he grabbed her prayer book and threw it on the fire with a roar of victory. He then had her forcibly ejected from the house by four footmen who hurled her into the street.

Afterwards, Jeremy could not but feel partly responsible. He endeavoured to make amends with a present accompanied by a tender note: My Dear Miss O'Shaughnessy. Please find enclosed a replacement prayer book. Also, a slice of the cake that you missed. I fear I must apologise for my father's brutality. Also for the dryness of the cake. Cook left it in the oven a little too long because she received news that her father had died suddenly. Sorry. I hope I may see you again. Affectionately yours, Jeremy. But her parents returned his package with a stiff note.