Not much is known about Desmond's early life. Desmond did not graduate from university because he had to support his three brothers after something happened involving his father. The cause of the elder Hume's departure remains unknown. For a time, he served as a set designer for the Royal Shakespeare Company.
Desmond began dating a woman named Ruth in 1988 for six years. Ruth said the closest thing Desmond came to a religious experience in that time was when Celtic won the Scottish cup in 1989. Later that year, a week before their wedding date, Desmond woke up on the street after a night of drinking fueled by wedding fears. Brother Campbell, a monk at a monastery in Eddington, Scotland, offered him help, which led Desmond to believe he had a calling to become a monk too. Desmond entered the monastery. He impressed and surprised Campbell by keeping his vow of silence, earning status as a novice monk and the title "Brother." Ruth's brother Derek tracked Desmond down at the monastery and punched him, leading Desmond to seek out closure with Ruth. Ruth didn't buy Desmond's claims of a spiritual experience and told him he was just running away because he was scared. After this rebuke, Brother Campbell found Desmond drinking the wine that the monastery vineyards produced. He told Desmond that he did not think that he should be a monk, and obviously was meant for a greater purpose. As Desmond was getting ready to leave, he met Penelope Widmore, who introduced herself as she was picking up several crates of wine for her father, Charles Widmore. They flirted and she offered to take him back to Carlisle with her
Desmond's relationship with Penny developed, and they fell deeply in love. Desmond dated her for two years prior to meeting her father, who was apparently unaware of their relationship. Eventually, Penelope moved into Desmond's flat (he being too proud to move into hers). During this period, Desmond's "best mate" was a physics professor named Donovan.
One day, in late 1995 or 1996, Desmond was drinking while painting his flat. He fell off of the ladder, only to be healed by Penelope. Soon after this, he said to Penelope that he would go to his father's industry to ask him for a job. Penelope said that if he didn't get the job, it wouldn't be the end of the world.
Later that day, he went to Widmore's office and he eventually offered him a job. However, Desmond said that he was in fact there to ask for Penelope's hand. Widmore expressed his unfavorable opinion of Desmond, impressing upon him his valuation of Desmond as worth less than his MacCutcheon whisky.
He came out of the building angry, and tossed his tie into the ground. He passed near a singing Charlie Pace. It started to rain, and when he met with Penelope, he said that he was angry because of how Widmore treated him, and he said he had lost his tie.
A later day, he went to buy a ring in a jewelry store. However, he had second thoughts, and left without buying the ring.
Later, he met with Penelope and a photographer asked to take them a photograph. They agreed, and Penelope selected a background she liked. They took the picture, and two copies of the picture were given to them.
However, when Desmond noticed that he couldn't pay for at least one photograph, he said to Penelope that he couldn't be with her. Penelope left crying, and their relationship ended. Desmond went to a pub, and he listens in the background the "Make Your Own Kind Of Music" song. He then watches a goal in the soccer game. Soon after this, a man named Jimmy Lennon entered the pub with a bat, shouting that the bartender owns him money. Jimmy Lennon hit the bartender with the bat.
Soon after this, Penelope moved out, and Desmond entered the Royal Scots Regiment.
During his recruit course in 1996 at Camp Millar (north of Glasgow, Scotland), Desmond woke up from what he thought was a dream, in which he was in a helicopter in a storm. In reality, his consciousness was time traveling to December 24, 2004. Desmond continued to uncontrollably leap back and forth between 1996 and 2004. Confused when in the future, 1996-Desmond received instructions from the 2004-Daniel Faraday to meet him at Queens College Department of Physics in Oxford in 1996. After Desmond convinced Daniel that he had been to the future, 1996-Daniel Faraday explained that unless Desmond found a "constant," something familiar and meaningful in both time periods, he (Desmond) would likely have a brain aneurysm and die. Desmond decided that Penny would be his constant.
Learning that Penny had moved and changed her phone number, he met with Charles Widmore in London to get new contact information for her. Charles relented, giving Desmond Penny's address, confident that Penny would reject Desmond once and for all. Desmond took 2 days leave from the Royal Scots to visit Penny, explaining to her that he needed her new phone number but that he wouldn't call her for eight years. Confused and upset, Penny reluctantly gave Desmond the number. Desmond left Penny's house to return to the Royal Scots smiling contentedly, knowing that in the future he will have made a connection with her, saving his life.
Desmond managed to reach the rank of a lance-corporal before being dishonorably discharged and serving time in the Southway Garrison military prison for failing to "follow orders". His exact offense is still unknown. At his release, Desmond reclaimed his belongings, including his copy of Charles Dickens's Our Mutual Friend; the book he chose to be the last thing he read before he died, and thus did not check it in prison, to "avoid temptation."
While he was in the Army, Desmond did a six-month detail disarming munitions, a skill he would later have to put into use on the freighter.
Outside the Garrison, Charles Widmore waited for Desmond's release. Widmore revealed that he had intercepted all of the letters Desmond had sent to Penelope from prison. Widmore then attempted to bribe Desmond into keeping away from his daughter. Widmore felt certain Desmond would agree to the arrangement, since he believed Desmond to be a coward. Desmond, however, declined, and entered himself in a world sailing race sponsored by Widmore in order to prove his worth.
Desmond then traveled to America, where the race was set to begin. He arrived, however, short of money and a sailboat. Desmond met Libby Smith in a café, where she insisted on buying him coffee. During their conversation, Desmond confided in her his shortcomings for joining the race. Libby then surprisingly revealed her ownership of a boat, the Elizabeth, which had belonged to her late husband. Upon her insistence, Desmond eventually accepted Libby's offer of the boat, promising to win the race "for love."
As Desmond prepared to train by running stairs at an L.A. stadium, Penelope approached Desmond and revealed her success in locating him by employing her great resources. "With enough money and determination you can find anyone," she explained. Penny asked him if he had read his beloved book yet, and inquired as to why he did not write to her. To evade her questions, Desmond confronted Penny with his knowledge that she is getting married, adding that he will be back in a year, after winning her father's race, and he hoped Penny would wait for him. Penny believed his choice to enter the race was just another example of cowardice. Desmond insisted that he is running to get his honor back.
Moments later, Desmond met Jack Shephard, while training at the same stadium. During their short conversation, Desmond suggested that Jack is running the stadium stairs because of frustration having to do with a woman. Jack confided in Desmond about his patient, Sarah, whom Jack had no hope of fixing. Desmond pointed to the possibility of miracles. Sarah's subsequent unexpected healing suggests that possibly Desmond was right. Since Flight 815 crashed on September 22, 2004, and since Desmond has been on The Island for three years, this would put the start of the solo race around the world some time during 2001.
Whilst racing across the Pacific, Desmond's boat was hit by a strong storm, during which Desmond wrapped his book in plastic, before getting knocked unconscious and falling off the deck. Soon after, he washed up on the Island's shore.
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