Lily Walsh first met Holden Snyder in the stables of her mother's house. Holden was the new stable boy and there was an instant attraction between them. When Lily felt neglected by her mother, she found comfort in Holden and his family. Lily found herself very comfortable with the Snyder family, whose down-home values were a welcome change to Lucinda's controlling nature. In addition to forming a very close friendship with Emma Snyder, Lily also became close with Holden's older sister, Iva, who seemed to be very protective of Lily. The reason for Iva's attitude toward Lily became apparent when Lily started befriending the older Rod Landry. Lily and Rod's relationship made Iva very uncomfortable and when she saw the pair innocently horsing around in the pond, a panicked Iva warned him to stay away from Lily because she was his daughter! It was then that Iva was forced to admit her deep dark secret--at the age of 13, she was brutally raped by her cousin Josh Snyder and ran off. She became pregnant and gave birth to a little girl who she gave up for adoption--that girl was Lily. Shocked beyond belief, Lily told Iva she hated her and then ran away.
Holden and Dusty Donovan both went off to look for her with Dusty finding her first. After Dusty called John Dixon to tell him that Lily was fine, he and Lily made plans to run off together but were found by Holden. When Lily learned that Dusty sold her out to John, she shunned him and sought comfort with Holden and returned home. Though there were concerns that Lily and Holden were related, Emma put everyone's mind at ease by relating that both Iva and Josh were adopted into the family, thus Holden and Lily weren't biologically related. Free to be together, the pair made plans to marry, however Lucinda disapproved of Holden more than Dusty and decided to put a stop to the relationship by telling Lily that Holden knew the truth of her parentage all along. Angry and hurt, Lily broke off with Holden and turned to Dusty, with whom she lost her virginity. Soon after, Dusty convinced her to return to Oakdale and then left for college himself.
Without Lily, Holden was lonely and he fell into the open arms of Emily Stewart. Holden impulsively married Emily, but quickly realized he made a mistake when he found out Emily was pregnant. Though he had decided to give his marriage another try after she miscarried, he quickly dumped her once he found out the baby wasn't his. After his divorce from Emily, Holden tried getting back together with Lily, but a series of events led him to believe that she was in love with his brother, Caleb. Holden and Caleb had always had a rivalry going on, and Holden was disgusted to learn how Caleb had callously dumped a pregnant Angel Lange, who ended up getting a bad abortion. Disgusted by Caleb's treatment of Angel (who Caleb had tried to hide from the family), Holden befriended her. However, Angel misread Holden's intentions and instigated a kiss, which was seen by Lily. Thinking she lost Holden, she became closer to Caleb, who Holden believed was using Lily for her money. Fed up with the situation, Holden quickly left town to sort out his life.
When Holden returned months later, he was married to Angel. Despite Angel's attempt to cement their marriage by adopting a child, Noelle (who was subsequently given back to her biological parents), Holden found himself pining for Lily. By now, he finally realized that he belonged with Lily and tried to get Angel to divorce him. Angel finally did give him a divorce and he did marry Lily, but not before he made love to Julie Wendall in a drunken stupor. Months later, Holden found out that his liaison with Julie produced a son who she gave to Iva to raise. Hurt and angry, Holden went to New York to confront her. After talking to Julie, Holden was mugged and lost his memory. When he finally resurfaced in Oakdale, he had no memory of his past with Lily and divorced her.
Holden eventually started experiencing memory flashes and tried to restart his friendship with Lily, since most of his memories seemed to be of her. Unfortunately, by then she was married to Damian Grimaldi. Lily was committed to her marriage and tried to discourage Holden. Meanwhile, Holden learned again that Aaron was his son and decided to sue Iva for custody. Though Iva tried to convince him that she was giving the boy a good home, the amnesiac Holden had no loyalty to his sister and ended up winning custody of his son. Meanwhile, in 1994, Lily was becoming disgusted with Damian's intense jealousy of Holden and finally having enough, she ran to Holden and the pair made love. However, she and Damian reconciled and, months later, Lily was shocked to discover that she was pregnant. Months later, Holden arrived at the Snyder farm to find Lily alone and in labor and delivered her son, Luciano (Luke). When it was learned that Damian was in fact Luke's father, Holden and Aaron moved to Maryland when Holden decided to go on with his life by entering a special memory recovery program.
In 1996, Holden returned to Oakdale and, after a blow to the head, regained his entire memory. By now, Damian was dead, so Holden and Lily were free to get married. Making matters complicated was Holden's old lover, Molly Conlan, who Lily met when she was in prison. Having had a child with Holden when they were teens, Molly confessed the truth to Holden, stating that she gave the girl up for adoption. In the course of finding their daughter, Abigail Williams, Molly attempted to destroy Holden and Lily's relationship so she and Holden could reunite. However, her plans failed and all she succeeded in doing was alienating herself from Holden and Lily. Meanwhile, when Lily learned that Damian did not die, she chose to remain with Holden, her true love and they married. Soon after getting married, Lily got pregnant. What should have been a happy occasion was marred by the appearance of David Stenbeck in their lives. David kidnapped Lily and planned on raising her newborn daughter as his own. With the police closing in, David escaped with the baby only to be found (without the baby) by Holden. After a struggle, David was shot and Holden, thinking he was dead, quickly buried him and withheld all knowledge of what happened for fear of what David's father would do. The only person who had any knowledge of what happened was Julia Lindsay, the fiancée of Holden's cousin, Detective Jack Snyder. The ordeal over, Holden and Lily named their baby Hope. However, unbeknownst to anyone, David switched Lily's baby with someone else's. After almost a year, Holden and Lily found their real baby, who was being raised by a very-much alive David! After the truth was discovered, the Snyders then renamed the girl Faith and gave Hope back to her birth mother.
To keep his mind occupied after giving Hope away, Holden accepted a job as manager of WOAK. Unfortunately, the job kept Holden away for great periods of time and he and Lily started to drifting apart, Though still committed to his marriage, Holden was unnerved by Lily's secretive nature about her relationship with Simon Frasier. Despite his doubts however, his love for Lily never wavered. That was until Lily returned from Atlantic City a changed woman. This Lily was cold and refused to sleep with Holden, which he took as a sign that she wanted a divorce. Angry and hurt, Holden was unnerved when mere weeks later, Lily begged him for a reconciliation. Put off by the sudden turnaround, Holden kept his distance but eventually gave in and made love to his wife, only to learn later that it wasn't! It seemed that the woman who came back from Atlantic City was NOT Lily, but her look-a-like, Rose D'Angelo. Holden then went on a quest to find his missing wife, only to find her in the arms of Simon Frasier. Disgusted at the state of his marriage, Holden moved out of the mansion. Holden quickly realized, though, that Lily was the love of his life the pair reconciled. As for Rose, she turned out to be Lily's twin sister.
Tragedy would strike again when Damian returned asking that Luke go to Malta with him. Suspicious, Holden and Lily refused only to learn that Damian planned to kidnap Luke. Trying to stop it from happening, Holden went to the docks to stop the kidnapping, only to be caught in an explosion. Presumed dead for weeks, Holden and Luke were actually imprisoned in Malta by Damian's greedy half-brother, Dante. Luckily, Holden was found and rescued by Lily, Simon and Damian only to have Damian run away with Luke! In the end, Damian returned Luke to his family and once Luke was out of danger (after the death of Dante), Holden made arrangements to adopt him. Months later at Christmas, Lily and Holden celebrated the birth of their daughter, Natalie.
After a few years of quiet family life, The Snyders would be thrown into turmoil due to the return of Dusty Donovan. Though Rose instantly distrusted Dusty, Lily tried to convince her that he was a great guy. However, soon the sisters would end up switching sides. When Lily learned that a down on his luck Dusty accepted money from Barbara Ryan in exchange for breaking up Rose's engagement to Paul Ryan, she felt betrayed. Learning of Dusty's involvement with criminal associates in Chicago convinced Lily that her old friend had changed for the worse and she warned Rose to write him off. However by this time, Rose had grown attached to Dusty and was certain that deep down he was a good person. The sisters found themselves in danger when Lily, mistaken for Rose, was kidnapped by Spangler (the man Dusty owed money to) and trapped in a well. Soon after, Rose was taken and trapped also. Luckily, Holden and Dusty found Lily, but Rose, who'd managed to escape, was nowhere to be found. Luckily, Rose was rescued that day unharmed. Reunited with her family, Lily implored Rose to cut her ties to Dusty. Though Lily was adamant, Holden suggested that it might not be wise to ask Rose to choose between her family and Dusty. Although Rose chose Paul over Dusty, the triangle ended in tragedy when after getting humiliated at the altar, Rose was poisoned and died.
Totally destroyed by Rose's death, Lily shut herself off from her family and secluded herself in Rose's house. Not knowing how she could live without Rose, Lily started to lose herself and talk and dress like Rose, to the horror of all around her. Not able to handle her grief, and unwilling to confide in anyone, Lily ran off to Atlantic City, impersonating Rose! Although Holden was able to find her, it was obvious that Lily wasn't doing well and, after Dusty blasted her for trivializing Rose's memory by acting like her, a distraught Lily ran off and attempted suicide by jumping into the freezing Snyder pond. Luckily, Dusty rescued her and Lily tried to go on with her life. However, she was unclear on how to do that and joined Dusty in his quest to ensure that Paul was arrested for Rose's murder. Although Holden tried to convince her to let the police handle things, Lily was determined to follow Dusty's lead and make demands on the police. Even after Barbara Ryan confessed to the crime, Dusty was unconvinced and kept digging into the matter until he found evidence that fingered Paul as the murderer -- computer files from Paul's computer that showed him visiting websites devoted to selling the drug, Methanol.
Thinking that it was beyond a doubt that Paul was guilty, Lily was shocked to learn that the killer was actually Paul's thirteen-year old brother, Will, who'd only wanted to make Rose sick, not kill her. Having found no peace in the arrest of a young boy, Lily continued to wallow in her grief and continually shut out Holden and the kids, choosing to spend most of her time at Rose's. Not knowing how to comfort Lily, but realizing that she needed to talk to someone, Holden reluctantly enlisted Dusty to help draw Lily out. Although she remained distant at first, in time, Lily accepted Rose's death and she and Holden bridged the gap between them. Meanwhile, Dusty's past would come back to haunt him when mobsters suddenly came around demanding money that he owed. Seeing no way out, Dusty laundered money out of the Foundation. Although he tried to keep his activities a secret, Molly discovered what was happening and told Holden and Lily.
Unfortunately, Dusty's dalliance with the mob would end up hurting Molly, when she was later approached by the Feds about what she knew. Although she said nothing, the mob boss, Starziak, was certain she'd talked to the agents and had her kidnapped. Luckily, Holden figured out what happened, and alerted Jack. Although Holden and Jack succeeded in rescuing Molly, Jack would later be declared dead when his car went into the river while transporting Starziak. Saddened at losing his best friend, Holden couldn't get comfort from Lily since she was preoccupied helping her former brother-in-law, Craig Montgomery, despite the entire family's assertion that he was unworthy. But the one person who did understand was Molly, who felt tremendous amount of guilt about what happened to Jack. While trying to reassure Molly that she wasn't at fault, the pair got close and kissed. Although they both pulled away, the kiss only made Molly feel more guilty and more determined to leave Oakdale. When Holden quickly confessed the kiss to Lily, it only increased the tension in the Snyder family. Wanting to focus on their marriage, Holden told Lily to get Craig out of the guest house and sever ties with him. Although she reluctantly complied, it became obvious that Lily was going to continue to befriend Craig and let herself be insinuated into his problems. After a year of Lily focusing on herself and other people instead of their marriage, Holden had enough and found himself drawn to a woman named Julia Larrabee. When Aaron was in critical condition following a boxing accident, it was Julia who helped Holden through it and not Lily. Soon the gulf between Holden and Lily widened and he leaned on Julia for support and friendship.
The final straw for the Snyder marriage was when Lily stood Holden up on New Year's Eve in order to help rescue a kidnapped Craig. Waiting alone, Holden encountered a lonely Julia and the two continued to bond. Days later, Holden decided to leave Lily. Lily couldn't bear it though and connived with Carly to get Julia out of Oakdale. However, their machinations only served to drive Holden further away and eventually into Julia's arms. Although Lily tried to plead with him to work on their marriage, Holden felt that he'd tried enough and refused. At the same time, Lily's actions toward Julia caused Holden to take out a restraining order against Lily for Julia. That action would have serious consequences. When Luke found out what Holden had done, he went to Julia's apartment and in a fit of anger, trashed her apartment. When he confessed to Lily about what he'd done, Lily went to the apartment to cover Luke's tracks. Unfortunately, Julia caught her in the act and the two argued, collimating into Lily shoving Julia. Unfortunately, Julia struck her head against the mantle place. Lily then left, leaving an unconscious, but alive Julia. However, that night when Lily returned, Julia was dead! Scared, Lily called Carly and they cleaned up the apartment to erase any evidence of Lily being there. However, the police suspected foul play. Holden's suspicions fell on Luke since he'd been hostile against Julia for a while. Afterwards, it was learned that Luke burned evidence of Lily being at the scene. Soon after, Lily confessed about the argument and stated Julia was alive when she left. However, things got confusing when Lily suddenly confessed to intentionally murdering Julia. When new evidence came along implicating Julia's ex-husband, Les, Lily finally admitted that she'd been lying to protect Luke.
While Les appeared to be the guilty party, Lucinda started suspecting that it was Julia's brother, Keith who was the murderer. Concerned since Lily was now becoming attached to Keith, Lucinda voiced her concerns to Holden who wanted to stay out of it. Despite himself, Holden started sharing Lucinda's concerns as well. However, he had trouble convincing Lily of that and she ultimately suggested that they should get divorced. In the end, Les turned out to be guilty after all and Holden was dismayed when Lily bonded even further with Keith. However, several weeks later, the relationship ended when Lily learned that Keith transported Lucinda, who was suffering from cancer, to Mexico for alternative treatment. Distressed by her mother’s decision to end her chemotherapy, Lily was livid that Keith went against her wishes to help her mother. Things got worse, soon after, when it was learned that Luke secretly boarded Keith’s plane and was lost in Mexico! Keith, Lily, and Holden traveled to Mexico to find him. Meanwhile, Lucinda finally told Lily Keith’s secret—he was illegally transporting human organs! While in Mexico searching for Luke, Lily and Holden wound up making love. Luckily, they were able to find Luke. After coming back home, Lily and Holden decided to work on their relationship just as Keith returned to town. Disgusted by what he did for a living, Lily ordered him out of her house and her life. Later, Lily and Holden received devastating news—his time in Mexico had damaged Luke’s kidney. He needed a transplant but no one was a match. That’s when Keith stepped in and offered o find a suitable kidney-for a price: Lily’s hand in marriage. Desperate, Lily agreed to the terms. Although she tried to keep the reason for her change of heart a secret, Holden figured out that the kidney came from Keith and that was why Lily was marrying him. However, a few weeks later, Lily decided that she couldn’t do it and pleaded with Keith to release her from her promise. To her relief, he did and Lily and Holden renewed their wedding vows. Not long after, Lily learned she was pregnant.
Meanwhile, Luke began hanging out with his friend, Kevin. Kevin was a party animal who continually encouraged Luke to get drunk with him. Despite the fact that a damaged liver could kill him, Luke did it anyway. On more than one occasion, his family found out and finally Holden forbade him from seeing Kevin. Meanwhile, Holden couldn’t help but notice Luke’s closeness to Kevin and wondered how close they really were. Convinced that Luke was hiding something, Holden continually tried to get him to open up but Luke kept pushing him away. His suspicions about Luke growing, Holden decided to peek into Luke’s lap top to uncover his secret but was caught read handed by an angry Luke. Meanwhile, at the same time, a young woman named Jade Taylor had entered the Snyders' lives claiming to be the daughter Rose gave up for adoption. Although the Snyders could verify that Rose did have a daughter, there was no proof that Jade was that daughter. Despite this, Lily decided to take the girl at her word. Meanwhile, Holden finally voiced his suspicion to Jack: he thought Luke was gay. While talking to Jack, Holden realized that what was important was Luke being happy; being gay wouldn’t factor into that. However, Holden still couldn’t bring himself to ask Luke the question.
Holden did ask Jade to report to him about Luke and she surprised him by telling him that he was wrong about Luke. Later, Jade was caught in a few lies, arousing Lily’s suspicions. Lily did some investigating and discovered that Jade was not Rose’s daughter—she’d been conning them. Lily was all set to throw Jade out when she and Holden found her in bed with Luke! Luke then shocked his parents by saying that he was in love with Jade. Despite the fact that Jade had betrayed her, Lily let her stay out of fear that Luke would run away with Jade. Holden’s suspicions came back though when Jade cryptically told Holden that sometime it was best not knowing. The suspicions grew even stronger when he saw Luke shove Jade away, but Luke stated it was because they were not allowed to be making out in the house. As the weeks went by, Jade's presence put a certain amount of strain on Lily. Luke though finally decided that his secrecy wasn’t worth it and confessed to his parents that he was gay. Ironically, it was Lily, not Holden, who had the most trouble accepting this fact. Not long after, who should arrive in town but Damian. Tensions flared between the two men because Holden was convinced that Damian was in town to manipulate Luke.
A few weeks later, tragedy struck when during an argument, Luke accidentally shoved Lily down the stairs, landing her in a coma. Incredulous, Holden demanded answers and Luke informed him that Lily had plans to send him to a camp that “reprograms” gay boys to be straight. However, Holden refused to believe that Lily would do that. He didn’t put it past Damian, though, but there was no connection between Damian and the head of the camp, Dr. Kreeger. As Holden kept watch over his comatose wife, the gulf between him and Luke widened with Luke (who believed that Holden blamed him for Lily’s accident) moving into Fairwinds with Damian. As the weeks went by, Holden’s initial anger toward Luke softened but he barely saw his son and Luke wouldn’t return his phone calls. Later, over a month after she’d fallen into the coma, Lily’s baby moved into the breech position. Holden was told that unless the baby was delivered now, it could die. On the flip side, there was a chance that Lily could die from the caesarian.
Realizing that Lily would never forgive him if he chose her life over their child’s, he told the doctors to go ahead with the caesarian. Luckily, both Lily and their new baby boy came through just fine. As Holden welcomed his new son into the world, things looked up when Luke agreed to come back home. Unfortunately, not long after Luke changed his mind and informed Holden that he had to stay with Damian since Damian was dying. However, Holden didn't buy that for a second and asked Lucy, now a doctor, to investigate. In the meantime, Luke was making plans to go with Damian to Malta. When Damian seemed in a hurry to leave, Holden and Jack rushed to the airport to meet them and confronted Damian. Suddenly, Damian’s colleague, Sergio, got desperate and held Luke hostage. Luckily, Damian diffused the situation and was forced to confess that he needed Luke in Malta to because he needed his inheritance. During the course of Damian’s revelation, Luke figured out it was Damian, not Lily, who wanted to send to a reprogramming camp. Angry that Damian had been playing him for weeks, Luke bitterly disowned his father and although he was within rights to pursue kidnapping charges, he declined in order to spare his family—the Snyders. Meanwhile, Lily would linger in a coma for months. When she finally emerged from her coma, she had no memory of being pregnant, though her memory did gradually return.
Throughout the following year, the Snyder marriage became more and more tenuous. Shortly after emerging from the coma, Lily had become obsessed with her weight and started taking diet pills. At the same time, Craig manipulated an already insecure Lily in order to get an “in” at Worldwide. Drawing on their long friendship, Craig offered to help Lily with a business deal with a baby food company she was negotiating and finally got Lily to unknowingly sign over WorldWide to him. Throughout all of this, Lily had developed a dangerous addiction to the diet pills. Not only that; her preoccupation with her weighted was having a detrimental effect on Faith--who had developed an eating disorder. When Holden confronted Lily about her problem, Lily realized the destructive effect she was having on her daughter, and sought help for her addiction. Months later, the already strained Snyder marriage came close to a breaking point when Lily got caught up in another man’s problems—Dusty. Soon after Dusty saved Lily from conducting business with a woman named Cheri Love, a madam, Cheri was murdered.
When Dusty was arrested for the murder, Lily not only paid his bail but also hid his gun. When she admitted what she’d done to Holden, he demanded that she give the police the gun or they were through. Afterwards, despite Holden’s demands that she stay out of it, Lily took it upon herself to help Dusty prove his innocence. Believing that the madam had to have had enemies, Lily (without Holden’s knowledge) went undercover as a hooker to get information. Finally, Dusty and Lily found the guilty party could very well be Col. Winston Mayer—Cheri’s ex-husband and the father of the man Luke had feelings for. In the end, Mayer (who had murdered Cheri) tried to kill both Dusty and Lily. The homophobic Colonel also attacked Luke but luckily was stopped by Holden. In the end, Mayer was arrested and Luke ended up temporarily paralyzed due to the attack. Angry over all of Lily’s secrecy this year, Holden suggested they separate. Later, after speaking with Bonnie McKechnie, Holden hired her as his divorce lawyer.
Meanwhile, as Lily began sleeping with Dusty, Holden was sharing an easy camaraderie with Bonnie. Though Lily made no secret of her desire to reunite with Holden, he insisted that their marriage could not be fixed. Then one day, Lily forgot to pick up Faith at dance class, Holden went looking for her and found her unconscious in her room. Luckily, he was able to wake her up and gently spoke about how worried he was when she didn't wake up at first. Lily stated that she was fine and let him know that it was over between her and Dusty. Seeing that Lily was distressed, Holden offered to take her to the farm to take care of her but backed off when Lily misinterpreted that as a sign that their family would be back together. Meanwhile, Holden’s plans to spend New Year’s Eve with his daughters were put on hold when the girls went to a sleepover. Holden ran into Bonnie and ended up spending time with her. Very soon after, Lily began acting erratically and ended up making scene at the farm upon seeing Bonnie with Holden. Meanwhile, Holden accepted Bennie’s invitation to be her date at a ceremony at Memorial Hospital. Also in attendance was an extremely agitated Lily. Concerned, Holden left Bonnie to find Lily. Soon,he found her unconscious in the corridor having overdosed on a bottle of pills. Lily had her stomach pumped. Holden angrily confronted Dusty and blamed him for Lily’s condition. He accused Dusty of using Lily and breaking her heart while Dusty accused Holden of pushing her away to begin with. Hours later, Holden returned to Lily’s room to find a syringe in her hand. After pocketing it, he got startling news from Lucinda: Dusty was dead.
Very soon after, Lily woke up and told Holden the same thing. Fearing that Lily had killed Dusty, Holden hid the syringe at the farm after deciding not to put it in a drug cart at the hospital. Unfortunately, Susan Stewart saw him at near the cart and notified the police. Lily was quickly released under Holden's supervision but had no memory of what happened the night Dusty died. In the meantime, Holden was being extremely protective and even tried to keep her from attending Dusty's funeral. Soon after, Holden was arrested when police found the syringe. Lily assured Holden that she'd hire the best attorneys but he refused. In fact, he refused to offer any kind of defense at all. Lily went to Bonnie asking her to help Holden and later posted his bail. In the meantime, Holden kept insisting that Lily that she had to take care of herself for the sake of her family. Soon, Lily remembered finding a syringe the night of the overdose and realized that Holden thought she killed Dusty. He was covering for her. Lily asked why and Holden explained that the night Dusty died they argued and Dusty called Holden on pushing Lily away. A regretful Holden admitted that he had been harsh on Lily and drove her into Dusty's arms. Lily understood. Though Lily knew she didn't kill Dusty that night, she suddenly remembered seeing his dead body close to the syringe. She also remembered seeing Emily rush out. Not long after, Lily got a call from a man claiming to have been working for Dusty. The man told Lily he had information that Dusty wanted. Fearing for his life, the man demanded that Lily come and meet him alone.
Despite her objections, Holden followed Lily and the two were shocked to find the man dead. Later, Holden learned that Lily rushed to Memorial after getting a phone call from Lucinda. When Holden went to the hospital, he was shocked to learn that both Lily and Lucinda were being held hostage by Evan Walsh. Apparently, in an effort to get his project approved, Evan drugged Bob Hughes and murdered Dusty when he was on the verge of finding out. Evan dragged the ladies to the roof but, luckily, Lily got the upper hand and stabbed Evan with his own syringe and was killed instantly. Afterwards, Holden and Lily decided to try to put their marriage back together. However, this time, there could be no more secrets. When Lily admitted that she had one but it wasn’t hers to tell, Holden surprised Lily by stating that he’d have to trust her enough to not ask for details. Unfortunately, harmony wouldn’t last for very long. Mere weeks later, Lily received a box full of Dusty’s belongings. Insecure, Holden asked Lily to get rid of the box. Lily complied but hid a few items away as mementos. When Holden found the missing items, he lashed out at Lily for keeping secrets since that was the entire root of their marital problems. Distressed at her own ability to be entirely honest with Holden, Lily decided to go to Iva’s for a visit to clear her head.
With Lily gone, Holden bonded with Carly, who was depressed over Jack’s rejection of her. Since he and Lily, Carly’s best friend, had been battling marital problems for years, he understood Carly’s dejection and provided support. Soon, fate kept throwing them together and Holden found himself getting to know Carly and appreciating her company. Finally, Lily returned but by this point, Holden was becoming attracted to Carly and the feeling was mutual. Recognizing that it was wrong, each tried to put a stop to it, but the pull was too strong and they couldn’t stop thinking about each other. Finally, came the day that the kids were set to go to camp. Though Lily was set to go with Holden, she was forced to back out and suggested that Carly and Holden go together. After they dropped off the kids, the pair almost shared a kiss. Rattled, Carly tried to distance herself from Holden and get him and Lily together. However, Holden couldn’t focus on Lily because he was too hung up on Carly. Finally, Holden kissed Carly. At that point, Carly tried to convince Holden that he and Lily had to go away and work on their marriage. She argued that their attraction was born out of mutual rejection and would subside if they were apart.
Fate intervened when Holden and Carly found themselves at the summer camp at the same time. Stranded due to a storm, the two were forced to share a cabin. There, the pair gave in to their desires and passionately made love. Afterwards, in an effort to alleviate his guilt, Holden moved back home with Lily. Though he tried to concentrate on his marriage, Holden couldn’t get Carly out of his head and became jealous when Lily set her up with Mike Kasnoff’s boss, Neal. Later, when Holden learned that Carly planned to go to Paris with Neal, he flew to the New York hotel where the pair was staying for the day before their flight to Europe. There, Holden confessed his deep feelings for Carly and offered to end his marriage for her. The two made love again and the next day, back in Oakdale, Holden confessed all to Lily. Given that he’d spent years preaching honesty, Lily was incensed at his betrayal and immediately sought a divorce. Though he still had feelings for Carly, Holden heeded his mother’s advice and tried to work on his marriage. However, Lily refused to give him a second chance. As for Carly, although she obviously had feelings for Holden, she felt that their relationship caused too much damage and stayed away.
Afterwards, Holden and Lily appeared to put their problems behind them and reconciled. However, one point of contention was Damian who had returned to town. Though Lily was convinced that Damian was a changed man, Holden was extremely skeptical. Later, on a trip to Kentucky, Holden was car-jacked by an escaped prisoner, who exchanged clothing with Holden and took Holden's watch and wedding ring to pawn. Holden tried to get away by swerving his truck off the road, but it broke through a railing, went over an embankment, and exploded upon landing in a ravine. Luckily, Holden was hurled from the truck before the blast. Unfortunately, he was found by an abusive man named Eb and held prisoner because Eb thought Holden knew where Skaggs, the man who hijacked Holden's truck, had hidden some stolen money. Though Eb’s wife, Maeve, was sympathetic, she was too afraid of Eb to offer any help. Unfortunately, when Maeve was finally convinced to help Holden escaped, they both were discovered by Eb. Eb locked the pair in a root cellar where they discovered the stolen money. After the cellar door caved in on Holden, Maeve took him to the hospital, and fled with the stolen cash. Meanwhile, Eb broke into Lily's house, and died in a tussle with Damian.
After several weeks of captivity, Holden returned home to discover that Lily had married Damian. Disgusted that Lily jumped into marriage so soon after his presumed death, Holden moved into the Lakeview. Since Holden had been legally declared dead, it was up to Lily to decide whether her marriage to Damian should be considered valid. When Lily seemed unwilling to keep Damian out of her life, Holden made the decision for her and opted out of their marriage.
At the same time, Carly informed Holden that Molly was unemployed so Holden convinced Molly to return to Oakdale. Meanwhile, Holden and Molly began investigating Meg's story that Damian had covered up the fact that the body found was not Holden's. Molly got Officer Grady to admit that Damian had blackmailed him; however, Damian warned her that her newfound information would only serve to reunite Holden and Lily, and Molly kept quiet about what she'd learned. However, Molly couldn’t stay quiet for long and confessed the truth to Holden. Meanwhile, an unhinged Meg crashed Damian and Lily's vacation, and as Meg and Damian fought over a syringe, Damian inadvertently choked Meg with her scarf. Thinking Meg was dead, Damian dumped her body in a trunk. Unfortunately, Lily found her and when Holden showed up, Lily told him everything. A revived Meg popped out of the trunk, and Damian fled. Luke informed Holden that Damian went on the run, and Holden confronted Damian at the docks. After a brawl with Holden, Damian disappeared and was presumed dead when a body matching his description washed up on the shore.
Though Holden was booked for murder, unbeknownst to everyone, Damian was alive. When, thanks to Molly, the Maltese government backed down on seeking extradition for Holden, Damian returned to Oakdale in secret and manipulated Faith to destroy the Snyder family. Faith tried to trick Lily into unwittingly meeting Damian, but under Lily's interrogation, Faith revealed that Damian was alive. Molly informed Holden that Damian had checked Faith out of her school. Holden escaped police custody, and Molly and he arrived at Damian's rendezvous spot to find Damian tying up Faith. Damian knocked Holden out and absconded to a warehouse with Lily. Though Damian tried to convince Lily that they belonged together, she was appalled at what he’d done and said that she was an obsession with him. Undeterred, Damian warned her that she’d change her mind after being alone with him at sea. At that point, Molly trailed them, and Holden arrived after Damian had locked Molly in a closet. Following an intense confrontation, police hauled Damian off to jail. At the police station, Luke finally denounced Damian and the Grimaldi name.
Meanwhile, her parents’ issues were taking their toll on Faith who began using drugs. Unfortunately, when Faith began confiding in Molly, Lily got jealous and demanded that Molly stay away from her children. Ultimately, Holden decided that Faith would be better off living at the farm with him. Later, when Molly was almost killed by a man named Silas, Holden asked her to marry him. Soon after, Holden and Lily hashed things out about Molly, and Lily professed her love for him. However, Holden told her that it was over between them, and she needed to let him go. Unable to deal with Holden’s impending marriage, Lily suddenly decided to go to France.
The day before the wedding, Lucinda convinced Holden to follow Lily to France and get her to come home. Holden convinced Lily to fly home from France, but bad weather grounded them in Montreal. He finally made it home, but Molly had already canceled the wedding. Realizing that it would never be over with Holden and Lily, Molly left town. Several weeks later, when Lily stood up to her mother, Holden began to remember why he fell in love with her.