Daddy Issues - Desmond David Hume
We learn that Desmond did not have the opportunity to go to
college, as his father died and he was left to raise three younger
brothers.

Relationship Issues - Desmond David Hume
Desmond dated Ruth for 6 years, and the two were set to marry. A week before the wedding, however, Desmond had some reservations about the marriage, and went to a pub to think things over. There, he aske God if he was doing the right thing, and blacked out. When he came to, he was being helped up in the street by a monk. Desmond took this as a sign that he was supposed to join the monestary, and abandoned Ruth.
Desmond
has found love and happiness with Penny Widmore. However, her father,
Charles Widmore, lets Desmond know that he thinks less of the love
connection. When Desmond asks for Penny's hand in marriage, Charles
refuses, asserting that Desmond is not nearly good enough for his
daughter. Clearly haunted by this, Desmond nonetheless decides that he
is, in fact, going to propose to Penny. Desmond is confronted by the
shop keeper from whom he wants to buy Penny's engagement ring who
discourages him from proposing, explaining that it is his fate to break
Penny's heart. And, in fact, when the moment comes to propose, Desmond
changes his mind, worried that he can not be the man that she needs,
and he throws her engagement ring into the Thames.
Still, Desmond is haunted by
Penny's allegation that he is a coward. To prove to Penny and her
father that he isn't, he decides to participate in Charles Widmore's
sailboat race around the world. And it is during this race that Desmond
finds himself crashed into the island.
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