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Penelope Widmore, aka "Penny" or "Pen", is the daughter of Charles Widmore. In "Live Together, Die Alone, Part 1" it was revealed that her father didn't want her in a relationship with Desmond, despite her love for him. Due to a brief interaction with Charlie, she knew there were survivors of the crash of Oceanic Flight 815. Thanks to a phone conversation with Desmond, she was able to track his location to the area near the Island, aboard the Searcher. There, she picked up a lifeboat containing the Oceanic Six, as well as Frank Lapidus and her long-lost love, Desmond.
Before Desmond's disappearance
In 1994, Penelope Widmore met Desmond at a monastery in Scotland, where Desmond had lived as a novice, but had recently been 'fired' from the order. Penny arrived at the monastery to pick up a shipment of Moriah Wine purchased by her father. Upon meeting Desmond, she convinced him to travel with her to Carlisle to deliver the wine. ("Catch-22")
Penny dated Desmond for two years, eventually moving into his flat, because he was apparently too proud to move into her larger one. After she moved in, Desmond met with her father, and was offered a job in the administrative department (which Desmond refused) at the Widmore Corporation, but was denied Mr. Widmore's blessing to marry Penny. Penny was pleased he was "spared the miserable existence under the employ of Widmore Industries", but was unaware of Desmond's request for marital blessing, so Penny decided they should celebrate. ("Flashes Before Your Eyes")
Desmond still planned to propose to Penny despite her father's refusal to give his blessings, but suddenly changed his mind after a street vendor took a photograph of the couple Desmond could not afford. He felt unworthy of Penny and unable to properly care for her, telling her that she deserved better. During the split up, Penelope called him a coward. ("Flashes Before Your Eyes")
A short time after, Desmond called Penny claiming he was in trouble and needed help. She said she was trying to get over him, had moved to a new place, and did not want to speak to him. She then changed her phone number. However, Desmond managed to obtain Penny's new address from her father (who gave it to Desmond because he was convinced Penny would tell Desmond herself that she did not want to see him anymore) and came begging to speak with her. She agreed to see him. Desmond explained that all he wanted was her new phone number, and he would not call her until Christmas Eve eight years in the future. Confused and hurt, she reluctantly gave him the number, 79460893, and forced him out of the apartment. ("The Constant")
Despite the breakup and Desmond's strange behavior, Penelope still loved him and never gave up on him. She placed a love letter in Desmond's copy of Our Mutual Friend before he was sent to military prison for as yet undisclosed reasons. However, he wouldn't find it until much later, after the accidental death of Kelvin, roughly three years after he shipwrecked on the Island. While Desmond was in prison, he wrote many letters to Penelope; however, her father had intercepted all of these letters before they reached her. As a result, according to her father, she got over Desmond and became engaged to someone else. ("Live Together, Die Alone, Part 1")
Her father's version of the situation was called into question when Penny tracked him down in the U.S. She asked him why he never wrote to her, and whether he ever had a chance to read his beloved book. When Desmond asked how she found him, she replied that "with enough money and determination, you can find anyone". Desmond informed her that her father told him about her engagement, which she didn't deny and only replied they hadn't yet set a wedding date. When Desmond implored he'd be back in a year, she responded, "what if you were back right now?", but Desmond ended the conversation by telling her emphatically that he'd be back in a year after he won her father's boat race to get his honor back. ("Live Together, Die Alone, Part 1")
After Desmond's disappearance
Soon after Desmond crashed on the island, Penny began searching for him. At some point, she managed to learn about the island, but the extent of her knowledge, and where it came from, is unknown. ("The Constant")
Season 2 (Day 67)
Three years after Desmond's disappearance, after the discharge and the detection of an electromagnetic anomaly by the two Portuguese-speaking men at the listening station, Penny was notified by telephone at 3:05 a.m., her local time, that they "found it." The callers referred to her as "Miss Widmore", seemingly indicating she was not married. On her nightstand was a copy of a similar photograph of her and Desmond as the one that Desmond carried. ("Live Together, Die Alone, Part 1")
Season 3 (Day 91)
Not long after, a helicopter crashed offshore of the Island, and a parachutist landed in the jungle. Desmond's flashes convinced him it was Penny, but it turned out to be Naomi Dorrit instead. A book Naomi was carrying had a copy of the photo of Desmond and Penny inside ("Catch-22"), and Naomi claimed that, although she had never met Penny herself, Penny hired Naomi's company to investigate the coordinates of the anomaly, which appeared to be in the middle of the ocean. ("The Brig") ("Through the Looking Glass, Part 1")
After Charlie turned off the signal jam at The Looking Glass, a button lit up telling Charlie there was an incoming transmission. He pressed the button, and Penny appeared on-screen, but her response to Charlie's question if she was "on the boat" was "What boat?" When Charlie clarified and mentioned Naomi, Penny seemed confused and replied, "I am not on a boat; who, who's Naomi?" As she asked how he got this frequency, she heard Charlie shout for Desmond. Penny smiled as Charlie assured her that Desmond was fine, however, Charlie was interrupted by Mikhail, the man who was presumably killed by Desmond before Charlie entered the transmission room. Mikhail, who had escaped into the ocean, was floating outside of the window and armed a grenade by the window of the room Charlie was currently in. The window shattered due to the explosion and the Looking Glass began to flood. Charlie, sacrificing his own life, shut the airtight door as to stop the flooding. Desmond shouted Penny's name as the door closed, but it was uncertain if Penny heard him. Charlie assumed Naomi had been lying about Penny hiring her company, so before he drowned, he wrote a message on his hand for Desmond, "Not Penny's boat". ("Through the Looking Glass, Part 1")
Season 4 (Days 94-108)
On Christmas Eve 2004, Desmond, on the freighter, phoned Penny at her London flat in front of a Christmas tree. She was ecstatic to hear from him, and relieved that this eight-year old prophecy had come true. She tried to tell him she knew about the island, and she vowed she would find him, but their connection was garbled and the full message wasn't understood by Desmond. They professed their love for each other just before the rigged phone on Desmond's end ran out of battery power. ("The Constant")
Due to that phone call, Penny was able to trace it to an area in the South Pacific where the Island was before it was moved. Early on the morning of December 31, 2004, her ship, the Searcher, came upon a lifeboat. It contained Jack, Kate, Sayid, Aaron, Hurley, Sun, Frank and Desmond, with whom she was finally reunited. ("There's No Place Like Home, Part 2")
After the rescue
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. Hurley, who objected to the idea of lying, questioned whether or not Penny could call off her father, who staged the fake wreckage of flight 815. Penny claimed that "there's no calling off" her father. ("The Lie")
After a week, Penny helped send the Oceanic Six off to the island on Sumba, where their cover story would begin. She showed signs of affection for baby Aaron, whom she handed to Kate before their departure. Desmond elected to stay with Penny on her boat, along with Frank. ("There's No Place Like Home, Part 2")
Some time during or after October 2005, Penny's father declared to Ben, who wanted to kill her in retribution for the murder of his own daughter, Alex, that he wouldn't be able to find her. ("The Shape of Things to Come")
At some point after the rescue, Desmond and Penny were married, as evidenced by wedding rings on their ring fingers. ("Because You Left") While sailing together in the Philippines aboard their yacht, Our Mutual Friend, Penny went into labor. Desmond searched out the nearest doctor, Efren Salonga, who helped birth their child, a son whom they named Charlie. ("Jughead")
Season 5 (2008)
Three years later, Desmond wakes up from a dream he had about his time on the Island. In the dream, Daniel Faraday confronted him during his time in the Swan, warned him that everyone that was left on the Island is in danger, and that he must find his mother in Oxford University. Desmond ran onboard, only for Penny to follow him, confronting him about his recent dream. Desmond claims it "was a memory", and told her they are going to Oxford. ("Because You Left")A day or so after, Penny interrupts Desmond as he is talking about Great Britain, saying that it is the place where Desmond broke her heart. Desmond tells Penny that he has to find Daniel Faraday's mother. She questions Desmond as to why he didn't remember this 3 years ago when he got back from the island, and Desmond does not have an answer. She has Desmond promise that he will not go back to the island, to which Desmond replies: "Why in God's name would I ever go back there?" Later, when Desmond comes home, he lies to Penny and claims that Faraday's mother has died. Penny sees straight through his lie and asks him why he is being deceitful.Desmond tells her that since he promised their journey would be over after visiting Oxford, he would not pursue it any further. However, Penny then tells him that she and Charlie will go with him to Los Angeles to find Faraday's mother. ("Jughead")
In a Los Angeles marina, Penny was aboard her docked yacht when Benjamin Linus arrived to take revenge on her, as he had promised Charles Widmore. After shooting Desmond, he was prepared to kill her before her son, Charlie, emerged from the yacht's cabin. Surprised, Ben hesitated, allowing Desmond to beat him senseless and throw him into the water. ("Dead Is Dead")
- Out of all the main characters, Penny has met only Desmond, Charlie (over a video transmission), Jack, Kate, Hurley, Sayid, Ben and Sun.
- As of Dead is Dead, Penelope's episode count is 10.
- Penelope's appearance has been a key moment in every season finale with the exception of Season 1, which was prior to her introduction, as she had nothing to do with the Hatch. Her appearances in these finales coincide with the dramatic climax of each season:
- The Listening station notifying her of the discharge in Season 2 ("Live Together, Die Alone, Part 1")
- The Looking Glass call and "Not Penny's Boat" message in Season 3 ("Through the Looking Glass, Part 1")
- The rescue of the Oceanic 6 aboard the Searcher in Season 4 ("There's No Place Like Home, Part 2")
- In Greek mythology, Penelope was the faithful wife of Odysseus who awaited his return while he was lost at sea. She fended off 108 suitors by weaving a tapestry which she insisted must be completed before she would remarry, but she unraveled her progress every night. The name has come to signify a loyal, capable, and clever woman. The name Penelope means "duck", but can also mean "thread".
- Penelope Widmore, as played by Sonya Walger, does not appear in the original version of Desmond's photograph as seen in "Man of Science, Man of Faith" and "Orientation". The woman appearing in the original version was claimed by some fans to resemble Arlene Stewart, who attempted to adopt Claire's child, but it was later revealed to be a continuity error that was corrected before a later re-airing of that episode and before the DVD release.
- The area where she is from — Knightsbridge, U.K. - is a wealthy district of Central London where Lucy Heatherton is also from.
- For fan theories about these unanswered questions, see: Penelope Hume/Theories
- Why is Penelope having the crew of the listening station look for magnetic disturbances in relation to her search for Desmond?
- Why did The Looking Glass receive a transmission from her?
- Why was the freighter crew under orders to block her incoming calls?
- How does she know about the Island?
- Who is Penny's mother?