Before coming to the Island, Desmond's life seemed to be defined by failure. He was fired as a monk, sadly broke up with his girlfriend Penny Widmore, dishonorably discharged from the Royal Scots Regiment, and regarded with contempt by Penny's father Charles Widmore. In an attempt to regain his honor, Desmond entered Charles Widmore's sailing race around the world and consequently became shipwrecked on the Island.
Desmond spent three years in the Swan station until he discovered his partner Kelvin was secretly planning to escape. He confronted and accidentally killed Kelvin, and his negligence sparked the incident which crashed Oceanic 815. He left the Swan when the Oceanic survivors discovered it, and he joined them after a failed escape attempt as a charismatic, helpful member of the camp. He and Locke tried to test whether the Swan was a hoax, leaving Desmond to turn its fail-safe key to prevent disaster.
The resultant implosion gave Desmond premonitions. He predicted a parachutist's arrival and Charlie's eventual death. He traveled to the parachutist's boat and escaped it after making contact with Penny. He and the Oceanic 6 then encountered Penny's boat, which led them to rescue. Desmond and Penny married and had a son, and they hid from Charles Widmore till a dream convinced Desmond to seek him out. Widmore returned Desmond to the Island, where the Man in Black and Jack both used him to deactivate the Heart of the Island.
After his death, Desmond was the first to recall his life and he embarked on a mission to help his friends remember theirs. Eventually, he succeeded in awakening his friends and, along with them and Penny, moved on.
Before meeting the survivors
Not much is known about Desmond's early life. Desmond did not graduate from university because he had to support his three brothers after the unknown death or disappearance of their father. Desmond once mentioned (to Jack) that he had almost become a doctor. For a time, he served as a set designer for the Royal Shakespeare Company. ("Flashes Before Your Eyes")
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. ("Catch-22") Although he wasn't a monk for long, Desmond would continue calling people "brother" in affection and habit.
Relationship with Penny
Desmond and Penny quickly 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 hitting his head on the floor, and was splayed out in the red paint which pooled underneath him and splattered on the walls. Just after, Penny came home and seeing him on the floor went to help him. Soon after this, he told her that he would go to her father's industry to ask him for a job. Later that day, he went to Widmore's office and after a brief discussion was eventually offered a job. However, Desmond replied that he was not there for a job but to ask for Penelope's hand in marriage. Widmore expressed his unfavorable opinion of Desmond, saying that he was worth less than a shot of MacCutcheon whiskey.
He came out of the building angry, and tossed his tie to the ground. As he passed by Charlie Pace singing Wonderwall by Oasis, it started to rain, and when he met with Penelope, he told her that he was angry because of how Widmore treated him, also telling her he'd lost his tie.
The next day, he visited a jewelery store to buy a ring. However, he had second thoughts, and left without buying anything. Later, he met with Penelope and a photographer asked if they'd like a photograph taken. They agreed. Penelope selected a background she liked. After it was taken two copies of the picture were given to them. (Official Lost Podcast/February 20, 2007) However, when Desmond noticed that he couldn't pay for even one photograph, he said to Penelope that he couldn't be with her. Penelope left crying, and their relationship ended.
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 The Queen's 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. ("The 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. ("The Constant")
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." ("Live Together, Die Alone, Part 1")
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. ("There's No Place Like Home, Part 2")
Charles Widmore's sailing race
Outside the Garrison, Charles Widmore waited for Desmond's release. Widmore revealed that he had intercepted all of the letters that 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. ("Live Together, Die Alone, Part 1")
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 David. Upon her insistence, Desmond eventually accepted Libby's offer of the boat, promising to win the race "for love". ("Live Together, Die Alone, Part 1")
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. ("Live Together, Die Alone, Part 1")
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. ("Man of Science, Man of Faith") 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. ("Man of Science, Man of Faith")
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. ("Live Together, Die Alone, Part 1")
Stranded on the Island
The half-conscious Desmond was dragged from the beach into the Swan, by a man in a biohazard suit who later identified himself as Kelvin Inman. Inside the Swan, Kelvin tells Desmond that the outside environment is contaminated by a mysterious sickness, to which Desmond may have been exposed. Kelvin forcibly inoculated Desmond with a vaccine labeled with the Numbers. Kelvin instructed Desmond to inject himself with it every 9 days. Desmond learned the "push the button" routine, and watched the Swan Orientation film repeatedly, which raised many questions in his head, most of which remained unanswered by Kelvin. ("Live Together, Die Alone, Part 1")
After two years, Kelvin showed Desmond how to initiate the lockdown sequence, which Kelvin used to complete the invisible blast door map started by his previous Swan partner, Radzinsky. One night later, while drunk underneath the Swan's computer room, Kelvin revealed to Desmond the nature of the Incident, and the function of the fail-safe key, which he carried at all times but was never able to find the courage to use. ("Live Together, Die Alone, Part 2")
At an unclear point in the timeline, a group of survivors congregated at the rear door of the Swan. After the group received no response and left for the beach Daniel remained and continued to knock on the Swan's rear door until Desmond, dressed in a biohazard suit and wielding a rifle, angrily burst out. Desmond appeared not to recognise Daniel, and asked whether Daniel was his "replacement", much like Kelvin thought when he found Desmond. Daniel told a confused Desmond that he was "uniquely, and miraculously special", and that he was the only one who could save them. Daniel instructed Desmond to seek out his mother at Oxford in the event that the helicopter made it safely off the island. After this, Daniel disappeared in front of him. However, it is yet not clear why Desmond remembered this years later, around 2007, but this may be linked to the fact that, in linear "real time" this event happened after Desmond left the Island. ("Because You Left")
Crashing Oceanic 815: Days 1–44
Kelvin never allowed Desmond to take a turn analyzing the environment. However, on the day of Flight 815's crash, Desmond noticed that Kelvin's suit was ripped, yet he continued his trips, leading Desmond to wonder if the sickness was a lie Kelvin made up to keep him in the hatch entering the numbers. Desmond had his first adventure in the jungle when he subsequently followed Kelvin. Desmond saw Kelvin taking off the biohazard suit before marching toward the cove. At the cove, Desmond found his sailboat, apparently repaired by Kelvin, with which Kelvin seemed to be plotting his escape from the Island. ("Live Together, Die Alone, Part 2")
Desmond confronted Kelvin, after realizing the charade to which he was subjected, and in the struggle that followed, he accidentally slammed Kelvin's head against a rock, resulting in Kelvin's immediate death. After grabbing Kelvin's fail-safe key, Desmond ran back to the Swan, where he found the countdown timer had reached zero, and system failure messages were flowing across the computer screen. Desmond eventually managed to stop the system failure, although, unbeknown to him, his actions inadvertently released the electromagnetic charge that had built up during his absence from the Swan, which caused Oceanic Flight 815 to break up in mid-air and crash on the Island.
With Kelvin dead, Desmond was now on his own, and he spent the next 40 days in the Swan in complete solitude, carrying on the duty of pushing the button all by himself. In a moment of despair, Desmond contemplated ending his life. Sitting down with a gun in his hand, Desmond questioned whether anything in his world is real. He moved to open his Dickens' novel, when a letter fell out of it: a hidden letter from Penelope, in which she encouraged Desmond to never give up, emphasizing her love and her decision to always wait for him. In a fit of rage, Desmond started to sabotage the Swan's contents, when he suddenly heard pounding on the Hatch above. Turning on the bright light, Desmond looked up as the traumatized Locke peered down in return, causing both men to regain their hope. ("Deus Ex Machina") ("Live Together, Die Alone, Part 2")
With the survivors
Days 44–67 (Season 2)
After blowing open the Hatch and entering the Swan, Locke and Kate confronted the suspicious Desmond, who held them both at gunpoint. After Locke led Desmond into believing that Kate was more dangerous of the two, Desmond locked Kate in the pantry. However, this gave Kate a chance to escape through the ventilation system, to later intervene with Desmond's holding of Locke, and Jack who joined them, consequently resulting in Desmond's accidental shooting of the Swan's computer. After failing to fix it, Desmond decided to flee the station, claiming that everyone will die soon, but was followed by Jack. Upon their confrontation, Desmond recalled his off-Island encounter of Jack, and asked him about Sarah, before repeating the Numbers to Jack in case the computer was ever fixed. ("Man of Science, Man of Faith") ("Adrift") ("Orientation")
Desmond apparently set off on the sailboat in an attempt to escape the Island. His attempt, however, was unsuccessful, and after two weeks the boat sailed back toward the Island. When the boat emerged to the survivors, Jack, Sayid and Sawyer swam to it, only to find Desmond inside, who by then believed the Island to be the last thing left from a long-lost world. ("Live Together, Die Alone, Part 1")
Desmond was then approached by Sayid, who asked for his help in his plan of sailing to the Others' camp, but he refused. Desmond was sought out later by Locke, who brought him the Orientation video from the Pearl, debunking his whole conception of the Swan's function. Desmond then agreed to join Locke on his mission, to let the Swan's countdown end once and for all, without interference, and see what would happen. In their attempt, they locked Eko out of the computer room, using Desmond's experience in triggering the lockdown. ("Live Together, Die Alone, Part 1") However, in their ensuing conversation, Desmond learned from Locke the truth about the pounding he heard earlier on the Hatch door, and about the Pearl's log printout as well. ("Live Together, Die Alone, Part 2")
After reading the log, Desmond then connected the date of the plane crash to the earlier system failure he witnessed, leading him to conclude that he may have unintentionally caused the crash. Desmond then decided that the button must be pushed, but Locke, however, intervened and destroyed the computer. With no other resolution, Desmond felt compelled to use the fail-safe key, and thus descended to the Swan's passageways to turn on the switch. With the words "I love you Penny," Desmond turned the key (after making the sign of the cross), causing the discharge, and the unavoidable implosion of the Swan. ("Live Together, Die Alone, Part 2")
Days 68–91 (Season 3)
Mind travel to 1996
After turning the fail-safe key in present Island time, Desmond's consciousness re-entered his 1996's self. He arrived at the time after falling off the ladder, while painting his flat. When Penelope tried to heal him, he thought that everything about the future had been a dream. ("Flashes Before Your Eyes")
Later that day, while preparing to go to the Widmore's Industries, he noticed his clock marked "1:08", and these numbers were familiar to him. Penelope said that if he didn't get the job, that wouldn't be the end of the world. That phrase disturbed Desmond, and when hearing a beep that was like the one in the Swan, he was even more disturbed. However, it turned out to be the microwave, and Penelope asked what happened to him. He said that he just had a déjà vu. ("Flashes Before Your Eyes")
After talking with Widmore, he offered him a job in the administrative department, but Desmond revealed that the real reason he came was to ask not for a job, but for Widmore's permission to marry his daughter, Penelope. Widmore expressed his unfavorable opinion of Desmond, impressing upon him his valuation of Desmond as worth less than his MacCutcheon whisky. Desmond left, crestfallen and angered, but when he saw a singing Charlie Pace performing on a London street corner just outside, he recognized him, and he said that all those events had happened before. Charlie didn't believe him, and when it started to rain, everybody on the street left, thinking he was crazy. ("Flashes Before Your Eyes")
Desmond went to see Donovan. He was skeptical of Desmond's theory that he could be time-traveling, and asked him to predict what would happen next. Desmond foretold the outcome of a televised soccer game, only to be proven wrong. Later that night, he arrived in his flat and Penelope said she loved him. She said that they would celebrate their love the next day. ("Flashes Before Your Eyes")
The next day, he went to the jewelry shop to buy a ring. This time, however, he wanted to buy it, but Ms. Hawking, the jewelry store clerk, revealed that Desmond was not supposed to buy the ring, that he was supposed to have second thoughts and abandon Penny. She further claimed to know that Desmond's future would involve going to the Island and pushing the button in the Swan. She imparted some of her understanding about how the universe "course-corrects" to prevent people from straying too far from their fate. Desmond stayed in shock, and she asked him to go with her. During her discussion with Desmond, she predicted the imminent death of a nearby man. Hawking claimed to be unable to ultimately prevent the death of the man, explaining that "the universe has a way of course correcting," meaning that if she saved him from that death, he would simply die another way soon after. Desmond kept the ring anyway, determined not to succumb to fate. ("Flashes Before Your Eyes")
He later met Penelope near the River Thames and they had their picture taken in front of a marina backdrop. Upset with the thought that he couldn't even afford the £5 photograph; he came to believe that Charles Widmore was right: he wasn't good enough for Penelope. He told Penelope this, and she stormed off with mixed emotions of anger and sadness. In the end, Desmond made the decision predicted by Mrs. Hawking, and threw the ring into the Thames. ("Flashes Before Your Eyes")
Drowning his sorrows at a pub that night, Desmond realized that he was a day off in his prediction of the outcome of the soccer match. He heard the song, "Make Your Own Kind Of Music", and then he watched the same goal in the television, as in the original events. Knowing that he could change his fate, he prepared to leave the bar. However, Jimmy Lennon stormed into the bar, carrying a cricket bat and looking for the bartender. Desmond, knowing that the bartender would be hit, tried to prevent the altercation from happening the way he remembered it, but was hit with the cricket bat, sending his consciousness back into the future. ("Flashes Before Your Eyes")
Return to 2004
Desmond woke up, lying completely naked in the middle of the jungle with blood stains on his chest and body. As his memory returned, he realized that the Island and the events that had happened there were indeed real, and he began to cry and beg for another chance to change events in the past, to no avail. He recollected himself and began to run around looking for help, and, unbeknown to him, ran past Locke, who was also waking up after the Swan implosion. He eventually found Hurley, who was on his way back to the beach after his encounter with the Others at the Pala Ferry. Hurley told Desmond how Jack, Kate, and Sawyer were still with the Others.
On their way back, Desmond revealed his first premonition, while attempting to comfort Hurley over his worries about his captured group. To calm him, Desmond commented on Locke's intentions to go after them, and referred to Locke's yet-to-happen "speech." At their arrival, Desmond parted from the survivors, and stood by the sea, while the previously confused Hurley listened to Locke's rousing words about saving the missing Jack and the Others captured, leaving Hurley in shock as he looked back at Desmond. ("Further Instructions")
Later, Desmond approached Claire, in an attempt to persuade her to move down the beach, to allow him to fix her roof, but Charlie intervened. At his failure to convince them, Desmond borrowed a golf club from Paulo, which he used in constructing a lightning rod that he placed very close to the tent. Shortly after, the camp was caught up in a sudden storm, when a bolt of lightning struck the recently built lightning rod, on its way to the tent, leaving Charlie in shock, similar to that previously experienced by Hurley. ("Every Man for Himself")
Desmond and Locke were later joined by Sayid, in a meeting to discuss a rescue plan for Jack and his group. Desmond explained to Sayid that the stations equipment could be used as well in communication, and thus they required Sayid's technological skills in helping them search for a station where Jack could be possibly be held captive. The three head to the Pearl, joined by Paulo and Nikki, where Desmond helped Sayid in patching the monitors with available feeds from other stations, leading to the temporal appearance of the mysterious one-eyed man on one of the screens. Moments after, Desmond heard the Monster's familiar sound, and hurried above with the rest, to witness the last moments of the dying Eko, where he was then left with Paulo and Nikki while Sayid accompanied Locke back to camp to get shovels for the burial. ("The Cost of Living") ("I Do")
When Charlie and Hurley met up with them, Desmond suddenly rushed to the beach and dragged a drowning Claire ashore and resuscitated her. Charlie became suspicious and Hurley aided him in getting Desmond drunk on MacCutcheon whisky, so that he would divulge his secret. Charlie and Desmond got into a fight after Desmond was called a coward by Charlie. He jumped and strangled Charlie, claiming that Charlie would not want to know what happened to him when he turned the fail-safe key.
After the fight was stopped by Hurley, Desmond apologized, and was carried by Charlie back to his tent. Then, Desmond revealed that when he turned the fail-safe key, his life flashed before his eyes, but after, the flashes didn't stop. He has been getting precognitive visions, but they were to save Charlie, not Claire, and he is afraid that there are only so many times he can cheat fate before it catches up with Charlie, and causes his death. ("Flashes Before Your Eyes")
Later, he prevented Charlie and Claire from catching migrating seagulls, foreseeing that Charlie would die attempting to do so. He then caught one himself before being confronted by Claire and eventually telling her his secret. ("Par Avion")
Desmond later witnessed Nikki and Sawyer arguing, and told Hurley about it later while he was investigating Nikki and Paulo's apparent deaths. He appeared at Nikki and Paulo's funeral. ("Exposé") Later on, Desmond hunted with Sawyer and successfully killed a boar to the delight of the rest of the survivors. ("Left Behind")
Around Day 86, Desmond had another series of flashes which showed another instance of Charlie's death and something coming to the Island. Believing that Penny had found the Island and was on her way, Desmond gathered up all the people he would need for his mission that were present in his vision: Charlie, Hurley and Jin. Desmond explained to Hurley that he saw what he referred to as "puzzle pieces" to a puzzle that had no picture on the front of the box. Upon Hurley's further inquisition, he said that he couldn't divulge many details about what he saw, for fear of "changing the picture on the puzzle box." What he was specifically avoiding mentioning was that his vision showed Charlie being killed by one of Rousseau's arrow traps.
With the assistance of Hurley's memory of the location of the cable and Jin's chance discovery of it in the sand (as per the puzzle piece), the crew followed into the jungle for a "camping trip." Watching a helicopter crash in the beach, Desmond then pointed the group's attention to the sky further into the jungle to see a flashing red beacon. Following his instinct and his half-assembled puzzle, Desmond led the group onward in the direction of the parachutist. On the way they found pieces of debris from the helicopter including a Portuguese language copy of Catch-22 with a picture of him and Penny in it. Despite his conviction that everything had to happen exactly as in his vision he nonetheless saved Charlie once again. When they find the pilot of the helicopter it turns out not to be Penny but Naomi. ("Catch-22")
Naomi was injured in the crash, and Charlie, Hurley, and Desmond argued a bit on how to treat her. A call was answered after Hurley accidentally fires a flare gun, which ended up summoning Mikhail. Desmond agreed to let him go if he helped save her life. With treatment, they removed a stick from her lung, and Mikhail said it would heal in a day, or a day and a half. Desmond allowed him to leave, despite Charlie's protests, but not until after they recovered the satellite phone Mikhail attempted to steal. ("D.O.C.")
Believing that Jack was working with the Others, Desmond persuaded Jin, Hurley and Charlie to keep Naomi's presence in the camp a secret but it soon came out, first to Kate, then finally to Jack. ("The Brig")
While Jack was revealing his plan to blow up the Others' raiding party, Desmond has yet another 'flash.' In it, he saw Charlie inside a facility of some kind containing a yellow blinking light and a switch, followed by Charlie flipping the switch, turning the light off, and then drowning. This action, according to the flash, resulted in Claire and Aaron boarding a rescue helicopter. At first, Desmond hesitated to tell Charlie this, but later laid it out for him, explaining that Charlie must die if the group hopes to be rescued. After it became clear that the switch from Desmond's premonition was inside the Looking Glass station, Charlie volunteered to swim to the station by following the underwater cable, and Desmond volunteered to accompany him. Once he and Charlie had gone out onto the water in the outrigger to the point directly above the Looking Glass, Desmond volunteered to take Charlie's place. Charlie at first seemed to assent, but then knocked Desmond unconscious with an oar and tucked his final message to Claire inside Desmond's shirt before diving into the water. ("Greatest Hits")
When Desmond woke up, he was immediately met with gunfire from Mikhail, who had arrived to stop Charlie. Desmond was forced to dive down, and arrived at the underwater station to help Charlie. ("Through the Looking Glass, Part 1") After hiding, Desmond harpooned Mikhail as he attempted to kill Bonnie and Greta. As he and Charlie prepared to leave, Charlie communicated with Penny via a video feed. As Charlie shouted for Penny's missing love, Desmond saw that Mikhail has vanished. Desmond ran to the communication room, noticing Penny on the monitor. Charlie, acting selflessly, had no choice but to lock him out, after seeing Mikhail through the underwater window about to blow it open with a grenade. Desmond stared through the window on the locked door, trying his best to open the door, as the grenade exploded and the room filled with water. Charlie, in his dying moments, wrote a message on his hand in permanent marker for Desmond. Desmond read "NOT PENNY'S BOAT" and understood the message. He continued to watch helplessly as Charlie drowned. ("Through the Looking Glass, Part 2")
Days 91–108 (Season 4)
After Charlie's final warning, Desmond hurried back to the beach camp with the outrigger and rushed in to warn the survivors of Charlie's message. When it was determined that warning Jack over the radio was too risky, he joined Sayid, Bernard, Jin, Hurley, Sawyer, and Juliet on a mission to intercept the survivors on their way back from the radio tower.
After the groups reunited, Desmond was about to go tell Claire of Charlie's death; however, before he could, Hurley stopped Desmond and did it himself. Despite his extreme concern over what Charlie told him, when the survivors split into two groups, he appeared to stay with Jack's group, which continued to try to make contact with the "rescuers," rather than take shelter in the Barracks with Locke's group. He followed the main group of survivors to the beach while Kate and Jack pursued the downed parachutist. ("The Beginning of the End")
Sayid later uncovered the picture of Desmond and Penelope from Naomi. He suggested that they bring Desmond to the helicopter in order to shed light on the situation. Juliet went to retrieve him and join Jack, Kate, Sayid, and Juliet at the helicopter; however, Desmond was as clueless as everyone else. While Sayid, Kate, and Miles went in search of Charlotte, Desmond questioned Frank about Naomi's picture of Penny. Frank denied knowing anything about Penny and explained that he was not a higher-up in the operation. When Sayid returned with Charlotte, Desmond left the island in the helicopter with Frank, Sayid, and Naomi's corpse. ("The Economist") Later, when Jack tried to contact the freighter about the helicopter, a woman named Regina informed Jack that the helicopter never returned. Desmond's fate, along with Frank and Sayid, was unclear at this point in time ("Eggtown").
While flying to the freighter, Desmond admired his picture of him and Penny. When flying towards the thunderstorm, Desmond experienced a "time shift," causing him to jump between 1996 and 2004; in Desmond's mind, the events of 1996 were real, and the events of 2004 were a hallucination. Desmond returned from the second shift, confused and wanting to get out of the helicopter. Sayid restrained him, and after they landed on the freighter, the confused Desmond panicked, stating that he did not recognize Sayid nor anyone else. Keamy and Omar took Desmond to the sickbay so the doctor could look at him.
While at the sickbay, he met Minkowski, who was strapped to a bed. He said that "it" was happening to him as well. After injecting Minkowski with a sedative, the doctor examined Desmond. He then shifted back to 1996. When he returned, Frank and Sayid came into the sickbay with Faraday on the phone. Daniel asked Desmond where he should be. Desmond said 1996 in the UK. Daniel told him to find him in Oxford. He told him some numbers so the past Daniel could believe him and that he should say he knows about Eloise. After returning, Keamy took the phone from him and he, Frank, and Omar left the sickbay, locking Sayid and Desmond inside with Minkowski. After returning from another shift, Sayid said Desmond's name and Minkowski recognized it. He said that the freighter had been getting calls from Penny.
Determined to call her so he could stop the time-shifting and his inevitable death, Desmond left the sick bay with the help of an unknown person (Possibly Kevin Johnson) and went to the communication room with Sayid and Minkowski. There, Minkowski shifted again; when he returned, he died. Desmond began to show symptoms that Minkowski had before he died. With Penny's number and the radio fixed, Sayid called and Desmond talked to Penny. She said that she had been looking for him for the past three years. Before the battery to the phone died, they professed their love to each other and vowed that they would find each other. Desmond thanked Sayid and, having found his constant, told Sayid that he was "perfect" now. ("The Constant")
Afterward, Desmond was confined to the sick bay with Sayid. Frank claimed that they were imprisoned there because the Captain was angry at them for "busting out" of the sick bay and communicating with Penny. Later, Ray released Desmond and Sayid from the sick bay and took them to meet Gault, the captain of the freighter. Gault showed Desmond and Sayid the black box of a plane that was apparently Oceanic Flight 815, and insinuated that Ben was responsible for staging the crash of Flight 815 deep in an ocean trench. After the meeting with Gault, Ray lead Desmond and Sayid to their new room; there, they encountered Michael, who was using the alias "Kevin Johnson". ("Ji Yeon")
Later, Desmond looked on as Sayid interrogated Michael, and he did not prevent Sayid from blowing Michael's cover in front of Captain Gault. ("Meet Kevin Johnson")
After Frank returned from the island with the mercenary group, Sayid was briefly interrogated by Martin Keamy, and Desmond looked on, not offering any support to Sayid, although when the captain noticed that Keamy was acting up (possible "Cabin Fever" he referred to earlier) he did not disagree that it was time to get the people on the beach rescued as soon as possible.
After Gault stalled and got the ships tender ready for the two, Desmond got a blank look in his eyes (unclear at this point in time of it was a flash or not) before he told Sayid that he refused to return to the island, and watched on yet again as Sayid took off towards the island.
Later that night, Desmond watched as Frank and Gault tried to convince Keamy not to head back to the island from a safe area on a set of stairs.He saw the helicopter take off for a third time, fleeing from his position on the stairs. ("Cabin Fever")
After Faraday began to ferry survivors over to the freighter, Desmond helped Sun onto the boat and asked if everything was okay. She said it was fine, and he left her and Jin alone with Michael. He ran into a control room where he told a mechanic named Hendricks that the engines should be working and reminded him to follow a bearing of 305. Suddenly, a radar in the control room was not working. Hendricks told Desmond that he would not continue any further unless the radar works. Desmond ran into the room and noticed it was filled with C4 and screamed for Michael, who was catching up with Sun and Jin. ("There's No Place Like Home, Part 1")
Using his army knowledge, Desmond attempted to disarm the C4, only to find it booby trapped at every possible angle. Michael forced him to go save himself as the warning signal went on and Desmond fled the freighter on the helicopter. It was in the air that he witnessed the explosion of the Kahana, as well as the disappearance of the island. The helicopter later crashed into the Ocean and Desmond was pulled aboard a lifeboat along with the Oceanic Six and Frank. Unconscious and not breathing, Jack performed CPR on him until he awoke.
Early on the morning of December 31, 2004, the lifeboat was discovered by the Searcher, which was commissioned by Penelope Widmore. On the deck of the ship, Desmond was finally reunited with his long lost love. ("There's No Place Like Home, Part 3") During the following week after the rescue, the Oceanic Six, along with Penny, Desmond and Frank, built a cover story for the 108 days the survivors spent on the Island. ("The Lie") After being on the Searcher for one week, as the Oceanic Six were preparing to embark for Sumba, Desmond elected to stay behind with Penny on the boat. Jack warned him to not "let them find you", and told him that he would see him in another life before departing. ("There's No Place Like Home, Part 3")
After the Island: 2005–2007 (Season 5)
In 2007, Desmond awoke with a sudden memory of instructions from Daniel on the Island. He traveled to London, against Penny's recommendations, to seek out Daniel's mother, but no record of Faraday remained there. His search led him next to the home of Theresa Spencer, an old girlfriend of Daniel's, who was now permanently incapacitated. Desmond learned Charles Widmore paid for her treatment, so he confronted him and convinced him to turn over Eloise's address. Charles warned him to return to hiding after he found her because someone else was after him. ("Because You Left") ("Jughead") Desmond traveled to L.A. with Penny to find Daniel's mother, and he discovered Jack, Sun and Ben outside the same church he was visiting. He entered it and discovered that Eloise was the same woman that urged him, years before, to abandon Penny for the Island. He warned Jack against trusting her and then left. ("This Place Is Death") ("316")
The next day at the marina, Desmond returned to his sailboat to find Ben there. Ben shot him and turned to Penny. Their son's appearance made Ben hesitate before shooting, letting Desmond tackle him, severely beat him, and throw him into the water. Desmond's injury sent him to the hospital. He survived the ordeal, and reminded Penny of his promise to never again leave her. ("Dead Is Dead") ("The Variable")
Return to the Island: 2007 (Season 6)
Charles Widmore kidnapped Desmond, returned him to the Island keeping him sedated in a locked room in his submarine. When he woke Desmond and explained what had happened, Desmond attacked him and had to be restrained. Zoe then led Desmond to a solenoid coil chamber, where he saw someone had just died. Members of Widmore's team strapped Desmond down, he managed to break free, but not before the team switched on the generator, knocking him out with a blast of electromagnetism. ("Recon") ("The Package") ("Happily Ever After")
During his few seconds of unconsciousness, Desmond had a near-death experience, flashing to a time after his death. He witnessed a version of Oceanic 815 that did not crash, an apparently happy existence, and when he awoke, he thought another blast could return him to that world. Zoe escorted him from the building, and he followed willingly. Sayid then arrived, killing several of the team, and Desmond followed him just as willingly to the main island. The Man in Black, who appeared to be Desmond's old friend Locke, then met him and interrogated him about his recent experience. He then led him to a well and, frustrated by Desmond's lack of fear, tossed him in. Sayid arrived the next day to kill him, but Desmond dissuaded him by appealing to love. ("Happily Ever After") ("Everybody Loves Hugo") ("The Last Recruit")
Vincent discovered Desmond in the well, and Bernard and Rose rescued him from it. Sawyer separately arrived at the well to rescue him, but Desmond was already gone, so he left after a confrontation with Ben and the Man on Black. The Man followed Vincent's prints to Rose and Bernard's camp and threatened the couple until Desmond agreed to follow him. The group then met with Jack, Kate and Saywer, and Jack, Desmond and the Man in Black journeyed together to the Heart of the Island. Desmond let the two men lower him down, telling Jack he'd go to the world he'd seen. He lifted a large stone from where the light was brightest, but he didn't then flash anywhere. Instead, he began screaming in pain. The light went out, and the Island began to shake. Jack returned some time after and tied him to the rope that had dropped him, letting Ben and Hurley pull him to safety. The two discussed sending Desmond back to his family, and they later traveled off the Island. ("The End") ("The New Man in Charge")
Before his awakening
When Jack Shephard left to use the restroom, Desmond took the seat next to him. They had a brief conversation wherein Jack tried to remember if he'd seen Desmond somewhere before. It appeared that Desmond did not recognize Jack even though he appeared to struggle to remember if he'd seen him (Jack) before. When Jack later returned to his seat, after saving Charlie from choking, he found Desmond no longer there. ("LA X, Part 1")
At the baggage claim, Desmond helped a pregnant woman retrieve her suitcase from the carousel. He offered her a ride, but she declined. As they parted, Desmond predicted that her child would be a boy.
Desmond met his driver, George Minkowski, who drove him to the office of their boss, Charles Widmore. Charles greeted Desmond warmly, hailing the success of his business trip to Sydney. Their celebration was cut short when Charles was informed that Charlie Pace, the famous bass player hired to play at his wife's charity event that evening, had been arrested. Charles asked Desmond to pick him up from the police station and make sure he got to the event, which would also feature Charles's son, a classical musician. Before Desmond left, Charles spoke appreciatively of Desmond's work, remarked on how wonderful it must be for Desmond to live a life with no personal attachments holding him back, and offered him a shot of his expensive MacCutcheon whisky. ("Happily Ever After")
After Charlie Pace's release from jail, Desmond listened patiently to Charlie's barstool ramblings about his near-death experience and his new belief in true love thanks to a vision that came to him while suffocating. Charlie diverted the car Desmond was driving into the water at the marina in order to prove to Desmond the existence of true love, causing Desmond to have visions of Charlie's hand in the Looking Glass DHARMA station. When Charlie fled Desmond's guardianship at St. Sebastian Hospital, Mr. Widmore charged Desmond with delivering the bad news to Mrs. Widmore that Drive Shaft would not be playing at her son's classical/rock fusion charity concert. In contrast to Mr. Widmore's expectations of her reaction to such news, Mrs. Widmore did not seem concerned that the band would not be able to appear, but became quite upset when Desmond overheard the name of "Penny Milton" on a guest list and began to make inquiries. Mrs. Widmore upbraided Desmond; asked him why he should be seeking anything when he already had a great job, the perfect life, and the thing he wanted most in the world, Charles Widmore's approval; and told him that he wasn't "ready" to find the thing he now sought. ("Happily Ever After")
In spite of all this, Daniel Widmore told Desmond that Penny was his half-sister and informed him that she could be found that evening at the stadium. When Desmond introduced himself, he fainted at the moment Penny shook his hand, and appeared to recall the events of his previous life, including his experiences with the survivors; he also seemed to gain an understanding of the true nature of the flash sideways world. However, he quickly recovered and asked her to coffee. She accepted and told him she would meet him in an hour. Back in his limousine, Desmond asked George to attain the flight manifest from his flight from Sydney so that he could learn the names of all his fellow passengers and carry out some unspecified plan to reveal some greater truth to all of them. ("Happily Ever After")
Recruiting the others
A week after arriving in LA, Desmond met a depressed Hurley who had been confused and upset by his confrontation with Libby. Desmond suggested that Hurley ask Libby to explain where she claimed to know him from. Desmond later witnessed them embrace while on a date.
Desmond traveled to the school where Dr. Ben Linus taught and Locke was currently substitute teaching. Ben found Desmond watching Locke and inquired as to why he was there. Desmond told him that he was considering sending his son to the school (naming his non-existent child "Charlie"). As he saw Locke in the parking lot, Desmond immediately sped up and deliberately hit him with his car, leaving him writhing on the ground in shock. ("Everybody Loves Hugo") Later that same day, Desmond arrives at the building where his lawyer works, and he sees Claire and convinces her to see his lawyer before going to the adoption agency. The lawyer turns out to be Ilana, who is also Jack's lawyer for the reading of Christian's will. She's been looking for Claire, who is mentioned in the will. ("The Last Recruit")
Later, Desmond returned to the school's parking lot where he ran over Locke. While observing him, he starts the car, and Ben jumps in front of it, recognizing him as the man who had run over Locke days ago, and shouts for someone to call the police. Desmond gets out of the car and punches Ben. As Ben is held down on the hood, he says he won't let Desmond hurt Locke again. Calmly Desmond tells him that he is not there to hurt him but to help Locke "let go." Ben asks who he is, and Desmond replies by saying "Do you want to know who I am?" and then beats Ben violently. While he is being punched, Ben has a flash of Desmond beating him while they were at the marina in LA. Desmond leaves with Ben confused and laying beaten and bruised on the ground. Desmond then goes to the LAPD and asks to see a detective. He is brought to Detective Ford, to whom he states that he had beaten a teacher senseless and had run over a man in a wheelchair, and turns himself in. Desmond is taken to a holding cell. He smiles as he joins Sayid and Kate in the cells. Det. Ford arrives at the cells to hand over Sayid, Desmond and Kate for transfer. Kate makes her last bid for Ford to let her go, but while he looks tempted, he tells her it isn't going to happen. As they are traveling in the wagon, a smiling Desmond says that it is time to leave. Sayid says he is a crazy person who turned himself in. Desmond partially confirms this by saying that he ran over a guy in a wheelchair. He accepts that he is crazy but says the issue is whether they want to get out of here or not. He says that when the driver stops he will need their trust because after he sets them free he will exact a promise from each of them to do something. Kate and Sayid both make their promise, skeptically. The paddy wagon pulls to a stop and Officer Cortez frees the three, asking for her pay-off. A yellow Hummer arrives and Hurley jumps out. He remarks that he hadn't known Ana-Lucia was going to be there, but then realizes he shouldn't have said that when Ana says she doesn't know him. He gives her $125,000. Hurley asks Desmond whether she is coming with them but he says she isn't ready yet. Cortez leaves. Hurley points out his Camaro parked nearby, including keys and the other things they'll need. Sayid goes with Hurley, while Kate accompanies Desmond, who takes a cocktail dress from the trunk of the Camaro and tells her "We are going to a concert." ("What They Died For")
Soon after Desmond signs for a body outside Eloise's church. Desmond returns to the car and informs Kate that the body belonged to Christian Shephard. When Kate asks why Desmond broke her out of jail and why they're going to a concert, Desmond responds that no one can tell her why she is here - not meaning the church, but rather this place. He tells her his name, that although she doesn't realize it, he is her friend, and that what he wants is to leave. Kate asks where he wants to leave to and Desmond drives off to show her. At the charity concert Eloise Widmore joins Desmond at his table, saying that she thought she made it clear that Desmond should stop what he's been doing. Desmond says she did, but that he ignored her. She asks, "And once they know, what then?" and Desmond answers, "Then, we're leaving." With concern she asks if they are going to take her son. Desmond reassures her, "Not with me, no." After Claire gives birth to Aaron backstage, Desmond arrives and asks Kate whether she now "understands." Kate gestures that she does and asks Desmond, "So, now what?"
Desmond is next seen at Eloise's church where he is joined by Penny, Jack, Kate, Locke, Hurley, Libby, Sawyer, Juliet, Jin, Sun, Charlie, Claire, Aaron, Sayid, Shannon, Boone, Rose, and Bernard, all who have now realized the truth, mostly due to his direct and indirect intervention. After a time, they all sit down in the church pews as Christian walks to the back of the church through the middle aisle. Christian opens the doors of the church and glowing white light from beyond the doors washes over all present. They are engulfed by the light. ("The End")
- Desmond was the twentieth character to ever have a flashback.
- Since at the time of "Live Together, Die Alone, Part 1" he was a minor character, he was the third minor character to have a flashback.
- Desmond's episode count as of "The End" is 46.
- Desmond appeared in five episodes as a guest star prior to being promoted to main cast.
- During Season 4 and 5, even though part of the main cast, Desmond appeared in less or the same amount of episodes as some of the recurring characters. In season 4, Frank Lapidus appears in more episodes and Martin Keamy in the same amount of episodes as him, while in season 5 Richard Alpert and Phil appeared in more episodes and Ilana, Pierre Chang and Stuart Radzinsky appeared in the same amount of episodes as him.
- According to their stories, Juliet and Desmond both arrived on the Island in 2001.
- Desmond has never met Walt, Richard and Pierre. However, he has met the rest of the main characters.
- Desmond did see Pierre on stage at the concert in The End. He also saw Pierre on the Swan Orientation film.
- Despite both characters being around since season 2, the first dialogue spoken between Desmond and Ben occurred near the end of the season 5 episode "This Place Is Death".
- In "The Constant" Daniel references an off-screen event where he meets Desmond before he boards the helicopter. It's likely Desmond met Charlotte as well as Daniel because she was present at the time.
- Desmond met Ilana, Ana Lucia, Charlotte, Miles, Christian, Shannon and Boone in the flash-sideways timeline.
- Desmond has visited five of the ten known DHARMA Initiative stations: the Swan, the Pearl, the Hydra, the Looking Glass and the Lamp Post. Desmond, Kate and Jin have visited the most stations. However since Desmond isn't a survivor and Jin is dead, Kate has visited the most stations from the survivors.
- In order to purchase a boat for the race, Desmond needed $42,000. (Numbers)
- Desmond's order number, 42, is called out at Mr. Clucks when he meets Hurley in the alternate timeline (Season 6). (Numbers)
- On their first encounter, Desmond and Jack parted with Desmond saying "See you in another life, yeah?" ("Man of Science, Man of Faith") ("Orientation") As Jack and Desmond parted ways again, it was Jack who said "See you in another life, Brother." ("There's No Place Like Home, Part 3") The next time Jack said it in (The End), the two were precisely to meet in another life, the flash-sideways timeline.
- The record Desmond put on before he heard the explosion from the blowing open of the Hatch is "Make Your Own Kind of Music". ("Man of Science, Man of Faith")
- The performance of Oasis's single "Wonderwall" places the known start of Desmond's timeline no earlier than 2 October 1995 when "(What's the Story) Morning Glory?", the album containing the song was commercially released. The song contains the lyrics "because, maybe, you're gonna be the one that saves me"; Desmond saved Charlie's life repeatedly before Charlie finally sacrificed himself in "Through the Looking Glass, Part 2".
- According to the producers, in Desmond's original timeline prior to his consciousness's travel back to 1996, he did not get hit with the bat, and might possibly have had a different origin for the photograph. (Official Lost Podcast/February 20, 2007)
- Desmond is a fan of Celtic football club. Immediately before Desmond was caught drinking by Brother Campbell, he was singing the Celtic song, "It's A Grand Old Team". His ex-fiancée remarked that his only religious experience during the six years they dated was Celtic winning the Scottish Cup. ("Catch-22") Celtic are traditionally associated with Scottish and Irish Roman Catholics, while Protestants support their arch-rivals, Rangers.
- A noteworthy game in which Graybridge came back from two goals down in the final two minutes of the game to win helped trigger Desmond's memories of the future during his trip to the past. ("Flashes Before Your Eyes")
- Desmond's address was shown on an envelope in "Live Together, Die Alone, Part 1". The town he lived in, Halstead, exists, though the street does not, and the post code, which began with CO8, does not correspond with Halstead, the post code for which begins with CO9.
- An alternate ending scene for the Season 4 finale was shot featuring Desmond in the coffin to detract spoilers from leaking.
- Desmond was the man who caused the survivors to be stranded ("Live Together, Die Alone, Part 2"), but he was also the man who caused the survivors to be rescued by calling Penny. ("The Constant") ("There's No Place Like Home, Part 3")
- Desmond is the only character who notices the time flashes without time traveling, likely due to him being "special". ("Because You Left") Other past characters, such as Danielle and Ethan, do not notice the flash.
- Desmond holds the record for the longest streak of episodes for a main character to not appear, eight. He was absent from "LA X, Part 2" through "The Package".
- Desmond is one of the 3 main characters alive at the end of the series who debuted in Season 2. The others were Bernard and Ben.
- Although, Bernard was already mentioned in Season 1, Season 2 was his first appearance.
- Desmond is one of 22 main characters to have their names appear in a soundtrack title.
- Desmond is one of nine male main characters alive at the end of the series, not counting the flash sideways.
- The wine bottles Desmond loads onto Penny's truck at Moriah Vineyards bore the number "1989" on the wooden packing crates. 19+89 = 108, the sum of The Numbers.
- Donald Crowhurst (1932–1969) was a British amateur sailor who competed in a single-handed, round-the-world yacht race. Crowhurst entered the race in hopes of winning a cash prize after a some personal difficulties. During his attempt he struggled with insanity and developed a philosophical reinterpretation of the human condition centered on the number 243. The number 243 shows up several times in logs (which were mostly faked): he planned to finish the trip in 243 days, recorded a false distance of 243 nautical miles (450 km) in one day's sailing (which if valid would have been a record day's run at the time), and may have ended his life on the 243rd day of his voyage. In his younger days he was in the British army but left due to a disciplinary incident.
- David Hume (1711-1776) was an 18th-century Scottish philosopher, economist and historian, and an early advocate of determinism, generally structured around a lack of belief in free will. ("The Constant-Enhanced")
- For fan theories about these unanswered questions, see: Desmond Hume/Theories
- Why was he put in prison and then dishonorably discharged from the army?
- If Desmond had met Daniel Faraday when he was banging on the hatch door, how did Desmond not recognize Faraday when he returned to the island on the Kahana?