The following night Dexter dressed nicely and went to Judy's house for dinner. Judy was also dressed nicely but not spectacularly in a blue silk afternoon dress but during dinner made Dexter feel uneasy due to her moody depression. Judy explained that she was like this because the guy she liked was pretending to be rich while he was actually poor. Judy then asked Dexter if he was poor to which he responded "I"m probably making more money than any man my age in the Northwest." (Fitzgerald) .
Judy had mixed feelings for Dexter and a week later she took him to a picnic supper in her roadster but after supper she disappeared in her roadster with another man. Dexter was very upset and when Judy assured him that she never kissed the other man he knew she was lying. Dexter was twenty-four when the summer ended and lived at one of the two clubs that he had joined in the city. Dexter had the idea of going to New York and Taking Judy with him so he made a habit of going to dances where he believed he would see Judy.
Eighteen months after seeing Judy Jones, Dexter got engaged to a sweet and honorable lady named Irene Scheerer. Although Judy was everything to him Dexter reminded himself of all the pain and trouble she had caused and it occurred to him that he could never have her. During the following months Judy was gone and Dexter was seen more and more with Irene, for a while he was always asked about Judy but as time went on he was no longer asked, but told about Judy. .
One night at a club while Irene was home suffering with a headache, Dexter was surprised by the presence of Judy. She convinced him to go for a drive and while away asked if he missed her to which he stated that everyone did. Judy commented to Dexter that she wanted to marry him and Dexter was unsure of whether she was aware of Irene. Judy was aware of Irene and began to cry wondering why someone as pretty as she could not be happy.