Lily and Simon

Simon tells Lily the story of Beloved. Beloved was a woman who was in love with his great-grandfather during the turn of the century. However, his grandfather was married at the time and from a wealthy family. Beloved was his great-grandfather's true love and his grandfather wanted to be with her. Since he couldn't she took off to America and his great-grandfather never saw her again. After they hearing and being moved by this story, Lily finds out that Simon is an architect. She asks him to design a playroom for Luke. Simon agrees to do so when he's in town. As he is working on her room, Lily is doing research on her past family history. Her family history interest was sparked from the letter's that belonged to Simon's great-grandfather. Simon agrees to do the job but has an ulterior motive. He takes out a picture of a woman from the some year’s back that looks just like Lily.

Her husband Holden does not trust him because he is spending so much time at the house. He believes she should get references on him. Lily insists that there is nothing for him to worry about. As Holden spends more time at WOAK, Lily's friendship with Simon grows. Lily gives him a key to her house so he can come and go when he works on the room. Then one day, Simon comes in early and pretends to fall asleep. Lily comes in and asks him what he's doing there. He tells her that he was working late and fell asleep. Lily tells him that her Grandfather has a house he can stay in. Simon feels guilty about staying but Lily insists he does so he can make sketches in peace. Simon reluctantly agrees to stay. Lily notices how wonderfully Simon sketches pictures. She was planning on giving Holden a photograph for his birthday but asks Simon to sketch her portrait. He feels awkward about it knowing that Holden isn't his biggest fan, but Lily tells him that since it will be a surprise, Holden won't mind. Holden has to go out of town with Abigail to Paris so she can see her parents. That would give them the perfect time to work on the portrait.

Simon is searching Cal's thing telling himself that the diamond has to be around here somewhere. Holden comes with a security guard and catches Simon. He asks him what he's doing there. Simon tells him that Lily let him stay there while he's working on the room. Holden refuses to believe him. Lily then comes and Holden asks her if what Simon is saying is true. Lily tells him it is and Holden gets upset with her, and tells her that Simon can't stay there.

Lily gets a call on the answering machine from Sheila, and she says that Simon is not to be trusted and is a liar. When Lily confronts Simon about this, he tells her Sheila is unstable. She was romantically attracted to Simon and when Simon didn't share her feelings, she was very angry with him. It is out of spite that she said what she said. Simon tells Lily to talk to her husband to get the references. When he has a moment alone, Simon calls Mack, who is Sheila's husband and tells him that Sheila almost blew his cover. He then tells Mack that he almost feels bad for what he's doing to the lady he's working for. He asks him to put in a good word for him so he can keep this job. When Lily calls him, his references do check out. Simon later calls his friend to thank him.

One day when Lily, Simon and the kids are in the living room together, the smoke detector starts to go off. Lily hears that and wonders where the fire could be. Simon knows it's the family room he's working on. They all go out of the house. Lily then remembers that she left her pictures in there. Simon tries to dissuade her from going in there. Lily says that the pictures are the only link to her past and she must go and get them and rushes in. Emma comes by and notices the fire. Simon tells her Lily is in there because she's trying to get her pictures. Emma asks her why he didn't stop her. Simon tells her he tried to, but she wouldn't listen. He will do something about that now. He rushes in and sees Lily passed out on the floor. He sweeps her out and takes her outside. Lily wakes up and sees that her family is ok. She then remembers the pictures are still inside. Simon rushes inside to grab the pictures. He goes and brings a few and then reaches for a metal box holding a bunch of the pictures, but burns his hands. As the firefighters are extinguishing the fire, Simon is able to salvage a couple of them, but is put in an ambulance so he can be taken to the hospital to take care of his burns.

Lily, visiting him in the hospital, feels terrible about what happens to him. Simon thinks the fire is his fault but Lily says that the electricians were the ones who did the wiring, and that was the reason the room caught on fire. Simon's hands are heavily bandaged and Lily wonders how he's going to get by on his own. She tells him that he can stay at her place while Holden is away in Paris, because he's not going to be able to do things himself. Lucinda stops by and sees what is happening and thinks Lily is nuts. Lily tells her that she's only helping Simon and there is nothing for her to be suspicious about. Lucinda warns Lily to be careful around Simon. When Holden calls from Paris to check on Lily and the kids, Lily mentioned that there was a minor fire but nothing for him to worry about. After Lily gets off the phone, Simon tells her that she didn't have to lie. Lily didn't lie, just held some stuff back. If she told Holden everything, then he would have left Paris early and Abigail would have been cheated out of spending quality time with her parents. Simon tells her that he really should be leaving. Lily makes him promise to stay until he finishes the portrait that she was going to do for Holden. Simon promises to stick around for a couple more days until the portrait is complete.

One day Luke comes across Simon's picture of Beloved when he is coloring and misplaces it. When Simon and Lily come in the room, Luke asks his mom about why she dressed up so funny in a picture. Lily has no idea of what he is talking about and Simon quickly changes the subject. Lily then takes Luke to make him lunch. Simon searches the room frantically for the picture and has to stop once Lily comes back. Later, while Lily is alone, she comes across the picture. She secretly makes a copy and slips it back into Simon's bag. Lily realizes that Simon has been deceiving her and plans to make him prove that he's lying to her. In the meantime, she puts an ad out on the web if anyone is familiar with this picture.

Lily tells Simon that she's falling for him and would like to go out on a date with him. Simon who is taken totally by surprise agrees. Lily comes to Cal's (which he has moved back into, now that his hands are better) and dresses very similar to how Beloved would be dressed. She takes him to Java Underground telling him that she's falling for him, but her real motive is to get him to admit why he's really in Oakdale. Simon doesn't bite.

When Lily gets back home she checks her e-mail. She gets one from the Redhead and her e-mail says that she has a copy of that picture and asks why she cares. Lily said that she may be a family member and if they could meet. The redhead tells her that she has to work and can't get off time, could Lily meet her there? Lily tells her she'll be happy to. The redhead gives her information of where she works and Lily informs Holden that while he's working in New York, she will be going to Atlantic City to do some research on her family history.

When Lily is about to leave, Simon runs into her and asks where she's going. She tells Simon that she has to go. Lily asks him if he's going to tell her why he's really in Oakdale and he won't. Lily then heads to Atlantic City. Simon goes to see the babysitter and finds out that Lily is in Atlantic City and decides to follow her. At the hotel, Lily comes in and is greeted by Mitzi who does a double take. She tells Lily that she will be blown away by the stage show. As soon as the show starts, Lily notices the woman who looks exactly like her but with red hair instead of brown. She meets her later and finds out she is Rose. Simon comes to the hotel and runs into Lily. Lily tells him to leave; she's here on business. Simon tells her that he's not going anywhere. Lily warns Rose to stay away from Simon because he's a dangerous man. She'll talk to her after her next show. Lily goes to her room and finds Simon there. Simon takes a gun to Lily and shoves her in the closet. Lily tells him to let her out because she needs to be somewhere. Simon tells her he's sorry but he can't. Simon attends the show and realizes that Rose is an exact double of Lily and deduces that she must have the diamond. After the show, Rose is waiting for Lily and is irked that she has been stood up. Once Lily is freed, she tries to find Rose but Rose has left.

The next day, Lily goes to see Rose before her show. She tells Rose that Simon is looking to get a diamond, after realizing that Beloved was wearing one in her picture. Rose didn’t know of any diamond, the stuff she had belonged to her mother. She told her that she only had costume jewelry and shows her the gem she used to decorate her headpiece. Lily wonders what if it's not. They test the diamond out on her mirror and realize it's the real thing. Lily tells Rose that she needs to get it appraised. Rose tells her that she has a show going on and will be fired if she misses it. Rose asks Lily to step in for her and she'll run to see her friend, who is a jeweler. Simon, thinking he's going to talk to Rose waits for the show to begin. Lily covers but Simon realizes that it's really Lily. He asks Lily where Rose is and Lily pretends that she is Rose. Simon doesn't believe her. Lily doesn't give up where Rose is. Little do they know, they are being watched.

When Rose meets up with Lily later, she finds out the diamond is worth over a million dollars. Lily tells her that they have to fool Simon in order for Rose to keep what's rightfully hers. They get their hair dyed the same color and get identical outfits. They see Simon and lead him backstage. They try to trick him by confusing him on which one is Lily and which one is Rose. Both girls run from him and all of a sudden there is a problem with the lights. Lily tells Rose if they get separated, for them to meet back in Oakdale. Rose takes the diamond and drops it into Lily's pocket. All of a sudden a gun goes off. One of the girls has escapes but the other one is hit with a sandbag and falls unconscious. The one who is waiting at the hotel goes up to Lily's room to meet her. Instead Holden comes and tells her that they are going back to Oakdale.

Meanwhile, the other finds herself on a train going to Canada. When she awakes, she sees Simon and talks as if she were Rose. She demands that they go back to Atlantic City. Simon tells her that they are on a freight train and it won't be stopping for some time. She then becomes unconscious and has a fever. She calls out for Holden and Simon realizes that he has Lily, not Rose. Lily tells him why doesn't he shoot her now with that gun he has? Simon tells her that the gun was never loaded. When the train stops he takes Lily off and steals a truck to get her to a place to rest.

While she's out, he gathers some of the leaves to help bring Lily's fever down. Then, he decides that they will go back to the room where Lily said the diamond was. While Simon is in the bathroom as they are waiting to get train tickets, Lily makes a phone call to her answering machine telling Holden that she is with Simon. Just then, the line becomes dead. Lily looks around for help and comes across a woman. She has an accent and Lily pleads for her to help her. She pulls a gun and tells Lily she is coming with him. Simon, realizing Lily is gone goes outside looking for her and runs into the woman with the gun. He knows her because she has turned out to be Celia, his sister.

Back in Oakdale, Rose is unsure of what to tell Holden, so she tells him that she thinks they should spend some time apart and that while she was in Atlantic City she had developed some feelings for Simon. Holden is devastated but understands considering everything Lily had been through. Rose then comes across the message on the answering machine and believes Lily has double-crossed her. Because of that, she decides she will stay in Oakdale and take over where Lily left off. She thinks Holden is incredible and her kids are going to need a mother, so if Lily is going to be that selfish, someone should look out for her family. Why shouldn't that someone be her? Rose calls her friend Mitzi in New Jersey to assist her with keeping things straight.

Lily and Simon find themselves in a plane being flown by Celia to parts unknown. When Celia gets to the location, she makes them jump out of the plane with their parachutes. Lily helps Simon swim ashore since he got knocked out, and they land on a deserted island. There is no one there and they have to make the best of it. Lily is furious at Simon for what he's put her through and they get off to a rough start. Simon apologizes to her but she won't have any part of it. Lily tells him that she'll find her own food and picks some berries, while Simon has gone out spear fishing. Simon comes back with his fish and Lily is about to start eating her berries and Simon tells her that they are poisonous. He invites her to have some fish and she eventually does. They later find a cave where they can sleep. Simon tells Lily, if they are going to survive this, they will have to work together. Lily, realizing he has a good point, puts her anger aside to work with him.

One day when Lily is taking a bath, her clothes have been stolen. Simon makes her a two-piece outfit from the parachutes they used to come ashore. She thinks it's Simon but it is really Cooley, a fugitive who has been wanted for murder and has been living on the island for several years. As Simon and Lily were working together building a raft, getting ready to leave the island, Cooley takes his machete and chops the completed raft to pieces. They are shocked. Lily worries that she'll never get off the island and back home to her family. Simon promises her that he will do everything to make up for this mistake. Just then Cooley comes and tells them that he hasn't been around a woman in over 25 years. He wants a night of good loving with Lily and if she doesn't comply, he'll kill them both. Simon tells Lily not to worry; he won't let Cooley hurt her.

The next day they gather some of the poisonous berries and make it into a liquid for Lily to add into Cooley's moonshine. Lily goes to Cooley's hut while Simon follows them closely. As they go into the hut, Simon gets trapped in a net. Lily is there with Cooley and stalls his attempts to get closer. She tells him that maybe they should have a drink before doing the deed. Lily then mixes the poison berry mixture in his drink and Cooley drinks it. Cooley tells Lily he's waited long enough and throws himself on top her of her. Lily screams. Simon, using a sand dollar cuts his way out of the net. When Simon gets inside, Lily is there and Cooley is dead. They decide to bury him and chalk the experience up to being a matter of survival. However, Cooley is not dead but just unconscious and frees himself from the shallow grave, unknown to Simon and Lily

In Oakdale, Rose is starting to fall for Holden and has moved back into the house with him. Celia comes to town one day and demands to know where the diamond is. Rose tells her that she doesn't have it that she gave it to Lily. Celia has a hard time believing her because she was with Lily and she said she didn't have the diamond. Rose tells Celia, if she had the diamond, she wouldn't be stuck in Oakdale. She goes on to say she dropped it in Lily's pocket when she before the shots rang out. Celia realizes Rose is telling the truth but not before she has snapped some pictures of Rose, Holden and the kids.

On the island, Lily has gone out to look for firewood and Simon comes across her raincoat. He feels something lumpy and comes across the diamond with fell into the lining because her coat pocket had a hole. Feeling betrayed that Lily lied to him; Simon decides that he is going to leave her there. The next morning Lily talks to Simon about gathering breakfast. Feeling that she should know how to fend for herself, Simon tells Lily about spear fishing. Later, Lily wonders what is bothering Simon, but Simon doesn't say much. He tells her he wants to work on the raft so he can get them out of there. Lily notices the raft is small for both of them. Simon tells her that it would be better if he goes alone and sends someone back for her later. Lily cannot believe that after everything they've been through he's going to leave her there by herself. She adds that if there is something she did to upset him then he should come out with it. Unless, he was just going through the motions about how he thinks about her. Simon confronts her about the fact that the diamond had been with her the entire time. Lily tells him she honestly had no idea. If she did, does he really think she would have let them both wind up on this deserted island? Simon comes around and accepts that Lily is telling the truth. They make up and he tells her he'll work on making the raft big enough for both of them.

The next day, a plane lands on the island. Just when Lily and Simon think they are going to get rescued, it is revealed that Celia is there. They hide the diamond and Celia takes them captive. She threatens to kill Lily if Simon doesn't give up the diamond. Lily lies about having it and Simon keeps mum. Celia tells them that she knows that one of them has it because she was in Oakdale and Rose didn't have it. She then goes on to taunt Lily about how she's not missed in Oakdale. She also makes insinuations that Simon is in love with Lily and tries to torture Simon with that. We hear the airplane motor running. All three of them run to the plane and see that Cooley is there and he's flying away. Celia shocked that she's now in the same situation as Lily and Simon loses her gun. Now that the playing field has been leveled, Simon tells Celia that he and Lily are going to sleep in the cave and she can fend for herself. She has been far too cruel and until she apologizes, they'll go their separate ways.

Back in Oakdale, Holden gets word that a woman matching Lily's description was seen in Canada at a train station. Holden asks his cousin Jack to check it out. Jack asks Julia to accompany him to Canada to help him out. Meanwhile, Holden asks Rose what really happened in Atlantic City because Rose has avoided it in the past. Rose tells him that she met a woman who looked exactly like her in New Jersey and was a showgirl. She probably ran away with Simon and split the profits of the diamond.

In Canada, Jack and Julia show a picture of Lily to the conductor and ask him if he saw anyone fitting this picture. The conductor identifies Lily and tells her that she was with a tall, dark-haired gentleman with an accent. Jack asks him if it would be possible that the security cameras have a picture of the two of them. After some time searching, the conductor comes up with a snapshot. It's dated June 18. Jack is puzzled by the situation but calls Holden to let him know that they are coming home and that he and Julia found something.

Jack visits Holden and shows him the picture. Holden remembers that he picked up Lily from Atlantic City back in May. He decides to confront this woman and have her tell him the truth once and for all. He asks Rose what really happened. She then says that she has already told him. Holden walks over to the desk where he stored the picture and shows it to Rose. He yells at her "Who are you?” She breaks down realizing that her web of lies has spun out of control and tells him who she really is. She did what she did because she believed Lily had run off with Simon and says that she has proof. She takes the answering machine tape she saved when Lily left her message from the payphone in Canada. After playing back the message for Holden, Holden realizes the line had been cut. He blasts Rose for her deceit and calls the cops to throw her in jail. He goes over to Cal's and rips into Mitzi for lying to him too. He tells her if she doesn't leave town, he will have her arrested just like he did Rose. Mitzi packs her things and quickly takes off. Holden then calls Jack and tells him of the events that just happened and asks him if he can check with his department contacts about the whereabouts of Lily and Simon. Jack hears that a fugitive who has been missing for several years has been incarcerated for a crime committed years ago. He had been living on a deserted island. Being his only lead, Holden tells Jack he has to talk to this guy.

On the island, Lily and Simon are working quickly to finish the raft. When they go to the cave, Celia pulls the gun that she had dropped into the hot springs from earlier. She tells them if they don't give her the diamond, she will make their life miserable. She takes out some pictures of Holden, Rose and the kids and tells Lily that she has been forgotten about. She lists the details of what has been going on while Lily and Simon have been stuck here. Simon, no longer being able to take her cruelty towards Lily gives in and tells her that he'll get her the dreaded diamond, if she wants it that badly. While Simon takes off to get the diamond, Celia keeps Lily captive and tells her that she can't understand how she got Simon to fall for her. Since Celia is a bit on the insane side, Lily takes what she is saying with a grain of salt. Simon gets back and tells Celia to send Lily over to him. Simon throws the diamond at Celia and asks her if she's happy now. Celia gleefully laughs after her long search, she finally has the diamond she's been searching for. She can now use the diamond for the life she never had and always wanted.

Lily and Simon stay behind while Celia goes out on the beach. Just then, Lily and Simon hear something. Celia has taken their raft with all their belongings. Simon runs out and tries to stop her but Lily holds him back, because the current is so strong. Celia, struggles with the current and drowns. Simon is devastated and Lily listens to him. Later, he tells Lily that the reason he wanted the diamond was to save his family's ranch in Australia. It had been in his family for many years and now he won't be able to keep it.

Down in Florida, Holden has arrived at the Federal prison and comes face to face with Cooley. He asks Cooley if he's heard about his wife but Cooley plays dumb. After giving in to Cooley's demands for his bail to be paid and a list of goods such as liquor and food, Cooley admits to Holden that Lily and Simon were on the island. The only way for Holden to find them is for Cooley to take him there. Holden having few options agrees. They set out on their way.

Lily and Simon have finally resigned themselves to the fact that they'll never be rescued and will have to adjust to living on the island permanently. They find some of Cooley's moonshine and get drunk. In their altered state, they decide to have fun and Lily starts humming some music for the both of them to dance to. As they slow dance together, Simon kisses Lily and Lily responds to his kiss. She then tells him to stop kissing her. Simon says ok but continues anyway. Lily slaps him.

Simon is surprised that she actually did that. Lily asks him if it hurt and Simon laughs that it did. Lily then on to say that she is married to Holden. She has known him half of her life and has wedding vows to that she promised to keep. While Simon is aware of that and respects that, he really believes that they are stuck on the island for good. Lily tells him to stop what he's saying because once he does, he can't take it back. She thinks she'll go out on the beach. Simon tells her that he's been holding in feelings for so long, he's going to choke on them. If Lily must run, then so be it but he can't go another 20 seconds without saying how he really feels. Lily stays and Simon admits how he's fallen deeply in love with her. Lily tells him they can only be friends. Simon says that if that's the way she feels, he will honor her request and will never speak of his feelings for her again. He has just one last request and that is for him to kiss Lily just one last time. Lily and him kiss and they fall onto the floor of the cave in the throws of passion.

Holden enters the cave and sees Lily and Simon together. He yells out Lily's name and Lily looks at him as if she is seeing a mirage and asks him "Holden is that really you?” She gets up and runs over to him and says that she had given up hope of ever being found. Holden scoffs that she seemed to be enjoying herself on the island. Lily insists that she and Simon had too much to drink and she got carried away. She tells Holden that he means nothing to her and suggests they go and talk on the beach. Simon looks at Lily as if he's been hurt by her comments and Lily shakes her head at him as if she didn't mean it.

On the beach, Holden is looking for Cooley but he's nowhere to be found. He's still angry with Lily for what he saw. Lily tells him that the whole time she was on the island the only thing that got her through was she wanting to be reunited with her children. Lily tells him about what she went through with Cooley and Celia and mentions that she found out all about Holden and Rose. She can't believe that she would believe Cooley and not believe the woman he's known half of his life. Simon comes out and tells him that he's not going to find Cooley. He adds that a storm is coming in so if they are going to get out of here, they better leave now. He is a pilot and can take them back to the mainland. Holden still ticked off at Simon agrees but punches him in the face and Simon falls flat on the beach with a bloody lip. Holden pulls out the gun he brought for protection and aims it at Simon. Lily pleads for him not to kill Simon. Holden tells her to give him one good reason why. Lily blurts out that if he kills Simon, there will be no one who can fly them back to Oakdale. Lily looks again at Simon as if what she said to Holden she didn't mean. Holden puts down the gun and they all board the plane as Simon flies them back home.

Back in Oakdale, Lucinda is curious about Rose and how she could look so much like her daughter Lily, without being related to her. Lucinda looks up Joe D'Angelo, who is Rose's father and visits him in hopes of getting some answers. She realizes that he's in New Jersey and goes there to speak with him. In New Jersey, Joe tells Lucinda that he hasn't spoken to his daughter in years. Lucinda tells him that Rose thinks that it's because he's ashamed that she is a showgirl. Joe tells her that he loves his daughter and that was not the reason. Lucinda asks Joe what the real reason was? Joe then tells him about how he had married his true love, Anna Marie. They had tried for years to have children but had no success. Then, a nun that new them both told them about a baby who was 8 months old that didn't have a home. The D'Angelos were able to adopt her and Anna Marie considered the baby to be her own. They named her Rose because her face lit up like a rose with her cheeks being red. As Rose got older, Joe had wanted to tell her the truth about her adoption, but Anna Marie would shut down and pretend that this wasn't the case. So, Joe kept this to himself and keeping the truth from his daughter, got the best of him. He became more distant from his daughter and Rose believed he didn't like her anymore. Joe tells Lucinda that he misses his daughter terribly. Lucinda convinces him to come back to Oakdale with her to see his daughter. He can see her and tell her now. Joe decides to go with Lucinda and they head home.

On the airplane, Holden is still mad at Lily for what she had been doing with Simon on the island. Lily brings up the fact that Holden couldn't tell that he was with an imposter for the time that she was on the island. Holden tells her that he suspected something was wrong, and when he would ask Rose about things, she would have an answer for everything. Lily has a hard time believing his story, but then Holden adds that Rose had Emma, Luke and Lucinda fooled. When they arrive at the airport, Holden tells Lily he needs to make a quick call. Lily tells Holden that she would like to say goodbye to Simon. Lily thanks Simon for everything and tells him that at least now he can go home. They share a heartfelt farewell as she lets him know that she'll never forget him. As Simon is trying to get a ticket back to Australia, two cops approach him and tell him that he's under arrest on outstanding charges for stealing a truck in Canada. He's put in jail at the Oakdale P.D. until he can be extradited to Canada.

Lily and Holden arrive home. The first thing Lily notices is the house is different and everything is rearranged. She mentions this to Holden who never realized that things were out of place. Lily gets angry with Holden and goes through the house because she needs to "deRose" everything. She later heads to the Oakdale P.D. to give Rose a piece of her mind. Little did Lily know that Jake had paid Rose's bail money to help him and Molly get even with Katie for stealing Molly's job. When Lily goes into the jail area, she is surprised to see Simon. Officer Shanks comes in and confuses her with Rose. Lily tries to explain that she's not Rose but Shanks doesn't believe her. Flustered, Lily talks to Simon and asks him what he's doing there. He tells her that the cops picked him up at the airport. Lily deduces that Holden is the one who called the cops, but Holden later admits that he had nothing to do with it. Since they are in closed quarters, Lily confides to Simon how everything is so different now that she's back and misses living on the island. Simon understands where she is coming from. Lily then asks him if he would be able to tell her from Rose. Simon tells her that he would know everything about her, every line on her face, every nuance of her voice. He then kisses her passionately. Lily kisses him back.

At Lily's house, Lily stops by and sees that Emma is with the children. She asks where Lily is and Emma tells her that Lily went to see Rose in jail. Lucinda rushes over to the jail and catches Lily and Simon smooching and blurts out "What on earth is going on?" She automatically assumes that Rose and Simon are making out but then Lily tells her it's really Lily. Lucinda is hesitant to believe her but when Lily says, "these are the eyes that have been looking at you all my life", Lucinda realizes that it is indeed her daughter. She calls Officer Shanks over to get Lily out. Shanks apologize to Lily and as they are about to leave, Lily stays behind to talk to Simon against her mother's wishes. Lily arranges to have Simon's charges dropped and gets Simon out of jail much to Lucinda's chagrin.

Simon is about to leave for Australia again. Lily intercepts him at the airport and asks him to stay. They've been through too much and she feels like Simon is the only person who really knows Lily. Lily puts Simon up in the Lakeview hotel but Simon refuses for Lily to pay his hotel bill. Simon gets a job as a mechanic at Burt's Garage as he waits for Lily's answer. Later when Lily is with Luke, Luke asks her about that funny lady who stayed with them while Lily was gone. Lily is thrilled that Luke was able to see the difference between the two sisters. Lily is very confused and asks both Holden and Simon for some time to sort out her feelings.

After taking the time, she realizes that Holden is the person she has always loved, and they work at bringing back their marriage to the level it was, before she left for Atlantic City. Lily tells Simon her decision but Simon believes that she's just doing what's right and thinks she will change her mind. Later, Simon goes down to the bar to have a drink and take in what happened. He meets Katie, who is living with her brother Craig and working for him now that she has lost her job at WOAK. She buys him a drink and tells him that whatever games Lily and Holden play they will always go back to each other. After she leaves, Simon shrugs off what she is saying. Lily and Holden work to bring the spark back into the marriage. They recreate their first meeting and start dating again. Still, no matter what she does, she can't get Simon out of her head. She shrugs it off and focuses on getting her family back to normal.

Lucinda is upset that Lily is so fixated on Simon and hates what it is doing to her marriage with Holden. Thinking that she could pay him to leave town and forget about Lily, Lucinda goes to the garage and offers Simon $20,000 to leave town. Simon refuses her offer without giving the money a second glance. Simon considers it but then turns it down flat. If he's going to leave town, it will be because what Lily wants. Meanwhile, as Katie is arranging the guest list for Craig's Masquerade party, she grabs an invitation and drops in on Simon's room at the Lakeview. She sees that he is packing his things and drops off an invitation. She tells him that even though she's not supposed to reveal who will be there, that Lily and Holden will be there tonight.

At the pool house, Lucinda drops in on Rose. She gets Rose to pretend that she's Lily by offering her $10,000 to convince Simon to leave town so Lily can work at getting her marriage back on solid ground. Rose heads over to the Lakeview to see Simon. Disguising her accent, she tells him that she's been thinking long and hard and feels it's best for Simon to go back to Australia. Simon agrees to go but he can't wait one minute longer to make love with Lily. After that, then he'll go. They kiss and start to undress each other. Simon leads Rose over to the door then opens it and shoves Rose out the door while keeping her top leaving her with only her bra and pants on. Rose, not understanding asks him why he did that and Simon retorts that she'll never be able to fool him when it comes to Lily and for her to get out of there. Humiliated, Rose goes into the Lakeview Lobby and demands a blazer from one the hotel manager. When Rose reports the news to Lucinda, Lucinda is not happy and realizes that she must take stronger action. She puts the INS on Simon's tail and tells them that he is illegally staying in the U.S.

The Masquerade Party turns out to be Lily and Holden's first time back in public as a couple. Katie is all dressed up and ready to go but finds out she was not included on the guest list. Infuriated at the oversight, she demands that Craig come out and clear things up. When she talks with her brother, she finds out that he did not include her on the list, to spare her the insults that the people in Oakdale would hurl her way because of what happened at the Endicott’s. Thinking that Craig is embarrassed and hurt by his actions, Katie heads back up to the suite and gets drunk off the brandy at Craig's. When she runs out, she heads down to the bar to drink some more. Wanting to be around Lily crashes the party. Earlier that day, Lily asked him to leave town, but since she had a hard time convincing Simon that she didn't feel anything for him, Simon believed that she was denying her true feelings for the sake of saving her family. After spotting her, he goes up to her and tells her that he loves her more than anything and kisses her passionately on the dance floor. Lily asks him how he could do this to her. Holden takes Simon out in the hallway and punches him out for kissing Lily. Lily asks Holden to stop. Katie is very drunk and runs into Simon outside the Lakeview. She's frustrated of how Craig is treating her and was angry that she's been assigned to cleanup of the party at 7:00 a.m. Simon who feels as though he's history with Lily takes off with Katie back to the garage.

At the garage, Katie and Simon drink some beers and Katie then tries to seduce Simon. She commends him for being such a gentleman and Simon tells her that he's not that much of a gentleman. They then have a wild night of passion. Katie offers him a condom but he throws it away and goes wild. The next morning, they woken up by Rose and Simon is shocked to see what happened. While Katie is getting dressed, Rose and Simon talk as she tries to convince him to work with her so she can have Holden and he can have Lily. Simon tells her that things between him and Lily are over and the same is probably with her and Holden. After Katie gets a cockroach on her, Rose takes it as her cue to go and warns Simon to keep an eye out for her. Alone with Simon, Katie is very amorous towards him and later he finds out she is a virgin. Simon tells her that she is not obligated to him in any way. Katie tells him that was the best night of her life and there's no way she's giving him up, even if he does love Lily. Katie believes that he'll never actually have Lily so she has just as much as a chance with him as anyone. After Katie leaves to go to work, Simon wonders what he has gotten himself into. When Katie goes back to the Lakeview and Craig fires her for not showing up to supervise the cleanup crew.

When they get home from the party, Lily tells Holden that she can't get Simon out of head and that she needs to explore her feelings for this man. Lily is also mad at Rose for interfering in their marriage. Rose had dressed up as Lily's double at the masquerade party and had taunted Lily that Holden couldn't tell that it wasn't Lily when they were briefly stuck on the elevator. Lily thinks that Rose and Simon will always come between them and suggests to Holden that maybe they need time apart. Holden is hurt and can't understand Lily's actions. Lily still loves Holden but is drawn to Simon. Holden packs his stuff and moves out to the farm.

He starts seeing Rose again and Lily goes the next day to see Simon after Rose has left. Simon is happy that she is here but surprised considering how she treated him the night before. She tells him that she told Holden she wants a divorce and wants to be with him. He had believed it was over. Lily kisses him and they start to get passionate on the hood of the car at the garage, but a twinge of guilt hits Simon about the night before with Katie, but regrets that he slept with Katie the night before. He tells Lily that he wishes he knew how she felt last night because he slept with a woman. When Lily asks him who it is, he says that she wasn't important and they were two souls who were sad and lonely. Lily is irked by it at first and then accepts that Simon is only human and acted in a moment of weakness. Simon is wondering why Lily isn't more bothered by it and thinks that if he were Holden, she would have been more upset. Lily tells him that is not the case, she just wants to move on and not dwell on stuff like that. She tells him that they will work around it to be with one another.

Meanwhile, after being kicked out of Craig's, Katie comes back to the garage while Simon is talking to Lily. She tells Lily that she needs her air-conditioning fixed, but Lily questions it since it is the fall. When Katie starts to hint at the encounter she and Simon had the night before, Simon cuts her off and tells Lily that he'll call her later. Annoyed that Katie interrupted him, Katie tells Simon that she has nowhere to go and asks Simon if she can stay with him. Simon lets her stay for the time being.

After a few stolen moments together, Simon and Lily dress up to go on a date at Java Underground. The INS is on Simon's tail so Katie distracts them to give Simon some private time with Lily. When the INS comes to the garage, Katie pretends to play dumb to stonewall the agents. The agents ask about Simon's whereabouts and Katie tells them he is not there. They notice the fresh tire marks and Katie tells them that they are from her car. To stall, she plays dumb and tells them that Simon is out at Luther's Corners getting daisies to make her a crown of flowers for her. The agents go off to find Simon. Katie then heads over to JU to find Simon. At JU, Lily and Simon are dancing thinking this may be their last date together. Lily asks Simon how can he leave when she loves him so much? Simon not believing his ears asks Lily if she realized what she just said. Simon says that she finally told him she loved him. Admitting that she is in love with him gives Simon reason to stay and he will do whatever it takes to be near Lily. Lily tells him that she better go but they will get past the INS hurdle together. They kiss goodbye. After Lily leaves, Simon goes onstage and finds an electric guitar. He plays the blues to get his mind off his impending fate. Ruby who is there with Bryant comments about how the man on stage is involved in a passionate love affair. Katie enters and tells Isaac to let Simon know she is looking for him. Simon looks up and sees her. Katie tells him that she knows a way she can keep him in the country. Simon thinks it's impossible but Katie tells him what does he have to lose and to trust her. Simon agrees and as they begin to leave, Katie asks Bryant to use his car. Bryant initially says that he's not going to loan her his car, but when Katie threatens to spill to Jennifer that she saw him kissing Ruby, he swiftly changes his mind.

Simon calls Lily from the road to let her know that he and Katie are getting married to stay in the country. Katie calls Jen and Bryant and asks them to stand up for them at the wedding. Lily tips off Margo about Katie getting married at the next town. They take her up with a police escort so she can stop the wedding. Katie is wearing a pink dress with a matching hat that has a short veil attached and Simon is neatly dressed in a black suit. At the courthouse, Lily tells Simon that she's thinks it's a terrible idea for him to marry Katie because he's not in love with her. Simon knows that it's not the best situation to get into but he believes it's their only hope of ever being together. Katie, who is not one to be shoved on the sidelines, tells Lily that Simon knows her intimately and Lily eventually figures out that Katie is the woman Simon had the one-night stand with. Lily is hurt and lashes out at Simon but Simon explains where he is coming from. Margo and Tom are just as shocked. Lily and Simon go to talk privately and Tom and Margo try to convince Katie that this is a bad idea. Katie has her mind made up and there is nothing either of them can do to change it. Jen thinks that it's ridiculous for her and Bryant to sit through a marriage where the two are not in love and leaves with Bryant.

Outside the courtroom, Simon tells Lily that whatever she decides, he'll go along with. Lily tells him that she does not want to see him get married. She'd rather he be deported than for him to be married to Katie, the same woman who tried to take her husband away from her. Simon then tells Katie that the wedding is not going to happen. Katie heads to the door and realizes the INS has pulled up and is starting to park. Lily, realizing that Simon not staying in the States is quickly becoming a reality decides to stall the INS so Simon can stay.

Inside, Katie shows the judge the marriage certificate and asks him to hurry. She tells the judge "Um, okay -- I, Katie, take you, Simon, to be my lawfully wedded husband. To have and to hold, to love and cherish, through sickness and health. For richer or poorer -- through rain, snow, sleet, hail and the darkness of night. Till death do we part, I do. Your turn -- ". Simon quickly says "I, Simon, take you, Katie, in richness and poorness and all of the other beautiful things that you just said. Right-o. Ditto. Right back at ya. Yada, yada, yada. Amen. Hallelujah. And oh, yes, I do." Simon slips the ring on Katie's finger just as the INS agents bust in. Simon will get to stay but the INS warns they will be watching them both. Katie throws her bouquet at Lily for her to catch since there is no one else around to do it. Simon sees the pain in Lily's eyes and feels terrible for leaving her alone, but with the INS breathing down his neck, he has no choice.

Back at the garage, Simon wonders if he should call Lily but Katie tells him that he would just tip the INS off. They are outside watching them. Reluctantly, Simon agrees and Katie convinces him to go to bed. When he gets into bed, he discovers Katie already there and is without clothes. Katie tells him point blank that this is how she goes to sleep every night. Simon warns her not to try anything and she agrees. He falls asleep thinking about Lily.

Craig offers Katie and Simon $1,000 if they come over to Margo's for the holidays. Thinking that they could use the money to take a honeymoon they never had the chance to take, Katie takes Craig up on his offer. Meanwhile, Simon spends time with Lily in trying to figure out the best way for them to be together without uprooting Lily's kids. Lily later tells Rose (after a tentative reconciliation) that it's not fair for Holden to wait for Lily when Lily isn't waiting for Simon. She gives Rose her okay to be involved with Holden.

Katie tells Simon about Craig's offer and how it would be great for them to go on their honeymoon. Simon is opposed at the idea and gets into an argument about it with Katie. The INS unexpectedly stop by and ask what the problem between the two newlyweds is. Katie covers by saying it was an embarrassing topic. Agent Hallowell says that he's heard a lot in his line of work so Katie tells them that they were arguing about how often they were able to have sex in a day. Agent Hallowell tells Simon that they will have to meet with him soon and they better have their stories straight. After the encounter, Simon realizes that working together with Katie, will be the only way he can be close to Lily.

For the holidays, Katie and Simon head out to Margo's while Lily and Holden take the kids to Lucinda's. At Margo's, Katie is surprised to learn that Lila, her mother is in town for a visit. She tells her how excited she is and is so happy her mom can finally meet Simon. Craig asks Simon to talk with him outside. Inside, Margo tells Katie that she thinks Katie is making a huge mistake. Katie refuses to listen to her negativity. Lila is upset that Katie made her life growing up with her mother sound so miserable. Katie tells her that she just doesn't understand. Margo tells Katie that she should be able to protect herself just in case. Tom brings her an agreement to annul the marriage. Outside, Simon gets a quick call from Lily telling him how much she misses him and wants to be with him. He tells her how he can do anything to be with her. Craig hearing this is bothered about how it's going to affect his sister. Simon lashes out at Craig for his wanting to control his sister. Craig tells Simon that he has to protect Katie from an opportunist like Simon. When they go inside, Katie is debating on whether to sign the papers. She rips the agreement into pieces and tells Craig to pay her the money he promised her and runs outside. Simon, who is pleased that Katie was able to stand up to her family, congratulates Katie on being such a pro. Katie takes one look at him and cries into his arms. Simon tells Katie that everything is going to be ok.

To work on their INS interview, Katie and Simon head to Bay City for their "honeymoon". Simon lets Lily know where he's going and tells her he's going to miss being away from her. On the train, Katie is talking to Simon but he's thinking about Lily. She tells Simon that she's hungry. In the corner of his eye, Simon spots a woman in a raincoat and sunglasses that look just like Lily. He gives Katie some money and tells her to get whatever she wants and to take her time. Simon is surprised that Lily is there with him knowing the INS have been watching him. Lily promises that they'll be careful but she had to spend some time with Simon. They kiss passionately. Lily then hears Katie's voice and throws back on her disguise. She rushes past Katie and knocks the food Katie is carrying out of her hand. Katie comments to Simon how the rude woman treated her and how he can't have anything to eat now. Simon tells her it's ok. Katie is disappointed that she didn't get to kiss him during the countdown. Simon is thinking of other things. They continue on to Bay City.

Hanging out in their Bay City hotel room, Katie tells Simon that she's hungry since they didn't get to eat on the train. She's going to check out the only restaurant that's open since they arrived in town late. Alone, Simon gets a phone call. It's Lily. She asks him if he has a moment and comes down to see him. They make out and talk about how they will be together soon. Katie comes back and knocks on the door. Lily hides in the closet. Katie asks Simon what took him so long to open the door. She then tells Simon that they need to get started on their questions for the INS. She starts to talk about sex. Lily is aghast and Simon thinks that's a poor choice considering Lily is right there. He avoids it and eventually Katie gives up and goes to get ready for bed. Lily sneaks out of the hotel room once the coast is clear, but her diamond bracelet is left behind. When Katie finds the bracelet she asks Simon if Lily was there. Simon asks her where she would ever get an idea like that. Katie shows him the bracelet and Simon covers telling her that it was a gift from him to her. Katie is touched at his gesture and thanks him. Lily boards a train back to Oakdale and the two newlyweds spend the remainder of their honeymoon together.

When they get back to Oakdale Simon and Katie go to meet with Agent Hallowell. Agent Hallowell asked them about their honeymoon and mentions that Lily Snyder was spotted in Bay City. Simon tells him that's ridiculous. Agent Hallowell suggests that Lily could have been hiding under the bed. Katie chimes in that Lily could also have been in the closet. Katie coughs because she did guess right and Agent Hallowell runs to get her a glass of water. Katie had asked Simon why he had lied to her about the bracelet. Simon tells her that he doesn't know what she's talking about. Katie shows him the inscription on the back, which said "To L, All My Love, H". Simon doesn't know what to say. Katie bluntly tells him that she is not planning to get behind bars. She does not want Simon to lie to her, that's one term she will not take. Simon apologizes and when Agent Hallowell comes back with the water, Katie thanks him for all that he did and keeps their cover.

Lily and Simon plan to move to Canada to be together. Katie, hearing of their plans calls her friend Henry to help her find a way to keep Simon. Henry comes over and as they brainstorm, he tells Katie that the one thing that will work is if she's pregnant. Katie thinks that's a great idea and later tells Simon the news. Simon, who is to say the least shocked, asks Katie how it could have happened when they slept together only once. She tells him that he was the one who threw away the condom. Simon begrudgingly calls Lily to let her know the latest development. Lily is hesitant to believe Katie's story. Simon tells her that he's planning to take her to the doctor to confirm if it is true. Katie then calls Henry and leaves a message on his machine to have him help her find a doctor who would be willing to lie about Katie being pregnant and that he must be from Peoria. Henry later calls Katie and tells her that she'll need $500 to pay the doctor off. Katie tells Henry she doesn't have that much money and begs him for a loan. Henry tells her he'll see what he can do.

At the doctor's office, a pregnant woman called “Henrietta” joins Katie and Simon. It's really Henry in drag, and he's there to give some background about this doctor. When Katie is about to go in and get examined, Henrietta tells her to check the paper for the family section and then leaves. Katie grabs the paper and finds the $500 Henry hid in the newspaper. After her exam, the doctor tells Simon that Katie is indeed pregnant. He lets Lily know and Lily doesn't know what to do. She feels that it's hard enough that this will affect her own family, but now there's an innocent baby. Also, the patience of her family is wearing thin and she realizes that she has to make a decision. Lucinda suggests that she go out of town for a few weeks to think things through. Lily agrees considering she's at odds of what to do about the two men she loves.

Meanwhile, when Henry dropped by to get the $500 back from Katie, since he's unemployed, Simon comes to the garage. He asks Henry what he's doing there and how he knows Katie. They tell Simon that they were close at WOAK. All of a sudden, Simon realizes that Henry was in disguise at the doctor's office. Simon asks Katie once and for all if she's really pregnant and demands the truth. Katie looks at him and tells him that she isn't. Furious that he's been lied to, he asks Katie why. Katie, embarrassed that she lied, runs out. Simon is fuming. The next day, Katie tries to explain but Simon won't hear of it.

Lily later goes to visit Simon and tell him that she can't be with him right now. Simon doesn't understand after everything they've gone through to be together. Lily tells him that it can't happen now that Katie is pregnant. There are too many lives being affected and it's just not fair. Simon tells Lily that it turns out that she was right about Katie not being pregnant. Lily tells him that it's too late and that it doesn't matter now. Simon, devastated tells Lily to leave and to not come back the next day telling him that she changed her mind. Lily begrudgingly leaves.

Simon is so heartbroken he lashes out at Lucinda. Since Lucinda brought the INS into their lives, she's responsible for coming between Simon and Lily. Simon gets very drunk and takes the car that was in the garage and crashes it through Lucinda's foyer. Lucinda calls the cops and Simon is arrested. Holden hears of Simon's arrest from Lucinda and thinks Lily should know before she leaves town. Lucinda tells Holden that Lily is confused enough and needs to make a clean break. If he tells Lily, then it's going to give her a reason to stay here with Simon. Holden knowing that Lily would be angry that the truth had been kept from her tells her anyway. Lily decides to leave town and not stop at the jail to see Simon.

When Lily finally gets back into town, Rose asks her to meet her at Java Underground so they can catch up. Rose is really setting Lily up to see Simon. Simon is now working for Isaac since he paid his bail when he destroyed Lucinda's foyer. When Lily goes to the bar to get a drink from Simon, she apologizes for how much she hurt him. Enough time has passed for Simon to be able to understand but he's not at the forgiveness stage yet. Lily tells him that she's still having problems reconciling with Holden. Rose tells Simon there's still hope for the both of them to be happy and get what they've always wanted. Simon doesn't say anything but after Rose pretends to leave, he calls Holden to see him, not knowing that Rose is eavesdropping.

When Holden comes, Simon tells him that Simon will always love her but he can't stand for Lily not to be happy. He repeats to Holden that nothing happened on the island between him and Lily. Lily loves him and he'd be foolish not to take her back. He give Holden a bottle of whiskey and tells him that he was returning the favor to Holden from when Holden brought him a bottle some weeks back to warn Simon about Katie. When Holden gets home, he and Lily talk. He forgives Lily and they reunite.