Gillian is left an inheritance of one thousand dollars by his late Uncle. He is required to report to the lawyer, Mr. Tolman, how he spends this inheritance. Gillian is at his wits end on what to do with the money. He thinks that his inheritance is a “confoundedly awkward amount.” The fact that he has to write a report on how he has used the money worries him even more. He states that writing a report will need “extra expenses, and perhaps the services of a secretary, as he is not good with account-keeping.” He even tells old Bryson that he intends to use the money all at once, “to chuck the money in a lump,” as he has to record his expenses, and he does not want to “itemize.” Gillian, thus, comes across as somewhat simple-minded. For, as old Bryson states, there are many things that a person can do with one thousand dollars. The fact that Gillian cannot think of a single constructive thing to do with the money, and that he has to go around town asking various people what he can do with the money, points to his lack of imagination.

It could also be said that Gillian is a respectful young man. Throughout the story, he speaks to people respectfully. When he gives Miss Hayden the one thousand dollars, he bows. Also, he is polite to Mr. Tolman when he meets him to take his share of the inheritance. Gillian is also a kind young man, for he decides to give his share of the inheritance to Miss Hayden. When the lawyers tell him that he is bound to get a further fifty-thousand inheritance in bonds based on how wisely he has spent his one thousand dollars, he tears up his report of accounts so that the whole amount goes to Miss Hayden. At this point, it appears that money no longer interests Gillian much.

Bobby Gillian is a man in love and he seems to be willing to do anything to express that love, including giving up, first a thousand dollars and then fifty thousand dollars to the woman he loves without her ever knowing about it. As in another O. Henry short story, "Gift of the Magi", Gillian's generosity is quite in line with the best principles of Christianity. He knows that neither money nor appearing to be rich will win the heart of Miss Hayden. He is self-deprecating and magnanimous. He displays incredible generosity and a carefree style which indicates that for Gillian, love is more important than money. In the end, it is doubtful whether Miss Hayden will ever love Gillian. When he confesses that he loves her, she simply says she is sorry. Gillian, however, cannot resist giving her the money anyway. It is for him only important that she be happy. Although he is initially portrayed as irresponsible and somewhat of a bore, he turns out to be quite passionate and honorable in the treatment of his inheritance.