Desmond's Island Experience

Desmond was engaged to Ruth, his girlfriend of 6 years, and set to be married, when one week before the wedding, Desmond had cold feet. He sought solace in a pub, and asked God if he was doing the right thing. The next thing he remembers, he is being helped up off the street by a monk and he has a religious calling. Desmond leaves his fiance for the monk's life, but is confronted by her brother, Derek (or more accurately, his fist). Desmond returns to Ruth to apologize and explain. When he returns to the abbey, his mentor, Brother Campbell dismisses him from the clergy, explaining that God has a different plan for Desmond. Desmond completes one last task for the abbey--he loads cases of wine into a woman's car: Penny Widmore's. 

Desmond and Penny had been together for two years when Penny moved in with him, prompting him to seek permission from Charles Widmore to marry his daughter. However 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. After this inident, it is presumed that Desmond joined the military to prove that he is not a coward.

Desmond Hume served as a Lance Corporal in the Royal Scots Regiment of Her Majesty's Armed Forces (British military) before he was court-martialed and sent to a military prison for disobeying orders. He left the last book he ever wanted to read ( "Our Mutual Friend" by Charles Dickens) in the custody of the prison guards. Upon his release, he was met by Charles Widmore, the father of his love Penelope Widmore. Charles revealed that he had intercepted all the letters Desmond wrote her, so she thought Desmond had forsaken her, and Penelope was now engaged to another man. Charles offered Desmond a great deal of money on the condition that he never had contact with her again.

Desmond refused the money, and some time later, he ended up in Los Angeles where he was planning to train in preparation for a solo sailboat race around the world sponsored by Charles Widmore. Unfortunately, he didn't have a boat. Desmond met Libby when she paid for his coffee. He jokingly asked her if she had forty-two thousand more dollar bills. She asked why, and Desmond told her that he needed a boat to enter Widmore's race and win, so he could get Penelope back. Libby told her that her husband David had bought her a boat (naming it Elizabeth, after her), but he had died. Oddly enough, Libby gave Desmond the boat, even though she'd only known him for a few minutes.

About three years before the crash, Desmond was training at a stadium when Penelope found him. He was surprised that she managed to find him. but she said that with enough money and dedication you can find anyone. She asked him why he hadn't written to her when he was in prison, but he didn't answer. He asked her when she was getting married, but she said that no date had been set. Desmond told her that he was going to win the race, and be back in a year. He said he was racing to regain his honor. A few minutes later, Jack was doing a 'tour de stade' of the stadium when he hurt his ankle. Desmond came over to assist him. Desmond asked why Jack was running. Jack told him that he made a promise to fix a patient of his, but he couldn't. Desmond asked Jack, "What if you did fix her?" Jack said that he didn't, but Desmond repeated again "But what if you did?" When Jack returned to the hospital, he discovered that Sarah was fixed. At the stadium Desmond also told Jack that he would see him "in another life," and sure enough, he later encountered him in the Swan.

Courtesy of tviv.org