In late summer of 1850, Austin Dickinson graduated from Amherst College along with his good friend George Gould, whose company Emily enjoyed. Gould was a tall, lanky man who was studying theology and hoped to be a minister. He made frequent visits to the Dickinson home. Because Gould's prospects were so poor, however, Edward Dickinson supposedly did not think him a suitable match for Dickinson or Lavinia. One rumor holds that George Gould proposed marriage to Dickinson, and she declined.
Young men began visiting Dickinson and her sister more and more often, but Dickinson took none of them seriously. In late 1850, Leonard Humphrey, Dickinson's friend and tutor, died of what was then called brain congestion. He likely died of an aneurysm. To Dickinson it was a crushing blow. She spent the next few months in a depression.
The next year, Dickinson's brother Austin began teaching at a boy's school in Boston. Dickinson was writing poems in her room, but told no one of how seriously she was taking her craft nor of the experiments she was conducting with structure and style, such as assonant rhyming patterns and dashes dividing lines into rhythmic sections. Dickinson spent almost as much time reading as she did writing. She devoured the poetry of Elizabeth Barrett Browning and read "The Atlantic Monthly," "Harper's," and "Scribners." She also read novels like Vanity Fair by Thackeray. She especially loved the novelists George Eliot and Thomas Carlyle.
In May 1851, the General Court of Massachusetts passed an act making Mr. Dickinson and four other men heads of the Amherst and Belchertown Railroad Company. They were charged with locating, constructing, administering, and maintaining a railroad through Amherst. The venture would require a great deal of capital up front, and Mr. Dickinson threw a huge amount of his own money into the deal. The railroad was completed in the spring of 1853. It was nineteen and a half miles long and connected with the main Massachusetts rail line into Boston. It was the first railroad to run through Amherst and was a resounding success. Austin came home from Harvard Law School, where he was studying, to watch the opening day festivities with Lavinia and Mrs. Dickinson. Dickinson elected to stay at home and watch the celebration from a hidden vantage point in the family's woods.
In the autumn of 1851, Dickinson met Henry Emmons, an Amherst College friend of her cousin John Graves. Emmons was a charismatic, well-read young man and Dickinson greatly enjoyed his company. The two embarked on a tentative and ambiguous romance, taking regular carriage rides and spending a great deal of time together. Like Dickinson, Emmons enjoyed writing poetry, and the two swapped poems regularly. Lavinia had just said goodbye to her boyfriend Joseph Lyman, who had gone South to complete his schooling. There was an understanding between Lavinia and Joseph that she would await his return and then they would marry. Both of the sisters' relationships ended in sadness. In the late summer of 1854, Dickinson discovered that Emmons had become engaged to someone else. In 1856, after five years of waiting–and after turning down at least one marriage proposal–Lavinia found out that Joseph Lyman had become engaged to a Southern girl.
Dickinson still enjoyed sending her short poems to friends to mark holidays and other special occasions. On Valentine's Day 1852, Dickinson wrote a poem and sent it as a Valentine to William Howland, one of the young men in her father's law office. Little is known about William Howland, but it is unlikely that he and Dickinson ever had a relationship. Howland was so impressed by Dickinson's poem that he sent it, without telling her, to the Springfield Republican newspaper. A few days later, while she was leafing through the newspaper, Dickinson caught sight of the poem printed on one of the pages of the Springfield Republican. She was mortified and successfully hid the newspaper from her father.