Halkett's first romantic relationship was with Thomas Howard. Although Howard was from a distinguished family, he was not wealthy. This meant that marriage between them would be economically damaging to both families. Halkett's emotions were caught between the economic difficulties the marriage would result in, and the pain and loss of credibility that Howard would suffer if she did not marry him. To prevent Halkett from making an imprudent decision, her mother guarded her by having another person sleep in Halkett's room and forbidding her from seeing Howard again. Rather than disobey her mother, Halkett said goodbye to him while wearing a blindfold. Her relationship with Howard created a rift between her and her mother that lasted for fourteen months. Although Howard vowed never to marry another woman, he later broke this promise. Halkett reported in her writing that his marriage was known to be unhappy.