Cheshire continued the practice of law until the early part of 1878. In summing up his work at the bar, he observed: "I made a living and saved a few hundred dollars. I had no very interesting or important cases, so far as I recall."[5] During his last year of practice, however, he made a little over fifteen hundred dollars, which, for a young lawyer of that period, was doing quite well. Since leaving St. Clement's Hall in June, 1871, Cheshire had not by any means devoted all of his time and thought to the study and practice of law. He accomplished a great deal more in the summer of 1871 than the study of common law under Mr. William K. Ruffin. It was then that he renewed his acquaintance with his cousin, Miss Annie Huske Webb, who lived in Hillsboro. He had seen this cousin but little since her visit to Tarboro in December, 1865. He always remembered the first time he saw her upon her arrival in Tarboro for that visit and described the meeting thus: "When I looked at her, as she came in out of the rain, and lifted the veil from her face, I thought her the most beautiful person I had ever seen. I think that first impression was never effaced."[6] In the course of the summer spent in Hillsboro Cheshire saw a good deal of his cousin. It was not long before he realized that he was in love with her. While not possessing a particularly romantic nature, Cheshire was a man of deep emotions and fine sentiments. During his courtship of Miss Webb he composed for her this little poem: A. H. W. My Love is a fair white Lily, And she loves not the day's full glare, But she seeks out a quiet valley, And she lifts up her sweet face there. The blue heavens through the branches Look down with their kindly light; And she smiles back a gentle greeting When the stars look through at night. The song-birds sing to her sweetly, And she's rocked by the gentle breeze; And she hides from the storms of Winter 'Midst the roots of the giant trees. She peeps in the crystal streamlet, As she nods in the breezes light: And she knows not her own fair beauty, But is glad that she's pure and white.[7] By May, 1872, Cheshire and Annie Huske Webb were engaged; but it was not until 1874 that he felt he was financially able to marry. On December 17 of that year they were married in St. Matthew's Church, Hillsboro. They had a simple wedding with Richard Lewis as his best man. The following day Cheshire and his wife went to Tarboro, where for the next four years they made their home with his family. With this, the greatest event in his life up to that time, we close the first phase of Cheshire's career. During the period he had grown to manhood, received his scholastic and collegiate education, taught for two years, studied law and practiced it for six years, and had some little part in the business world. All of this training and varied experience gave him a rich background for the great work which lay ahead of him.