In 1880 or 1881 Orlando reached the decision that Charlotte Gray, whom he always called Lottie, was the woman he wanted to marry. This was a very important step for him and he wanted to explain his feelings to Lottie as he asked for her hand in marriage, something that he wanted her to have time to consider before giving her answer. He chose to write a letter declaring his intentions because it would allow her time to consider her answer, and asked if she was willing to wait two or three years as he felt it was very important that he had time to establish himself so he would be able to properly support her. In his letter part of what he explains is that he knows little of her as he only sees her in the evenings, but what he does know is that she possesses smartness and common sense. Further on in the letter he discusses her concerns about who should be the head of a family, a topic she has spoken about jokingly when they have been with others. He states that a woman should have just as much interest in a husband's success as he should have whether it be related to business or home. Orlando also clarifies that he does not mean that he would ever allow any woman to take charge of him. He further explains that he is looking for a companion not a slave.

A further tribute to his intense love for Charolotte was Orlando's decision to be buried with her when he died in 1930.

Orlando Merchant had many vessels built during his years associated with the Gloucester fishing industry. One of them was named in honor of his first wife Charlotte, which was named the Lottie G. Merchant. The photo above shows members of her crew aboard the vessel, which was built around 1901. Ben McGray, wearing the necktie, was the skipper of the Lottie G. Merchant at the time of this photo. This page is the property of the Shute & Merchant website.