Lily Walsh met Molly Conlan in prison. Molly, who was in jail for unwillingly being an accessory to armed robbery, saved Lily from a fellow inmate. The two became friends and when Lily was released she helped Molly get her conviction overturned. Lily gave Molly a place to stay, and Molly told Lily about her first love and the child she gave away as a teenager. The father of Molly's child turned out to be Lily's husband, Holden Snyder. Molly had grown up near the Snyder family and she had ended up pregnant after sleeping with Holden. Her family then moved away and forced her to give her daughter up for adoption. Molly enlisted Holden's help to find their daughter and became infatuated with him again. She pulled a few dirty tricks to try to get him back, and ended up alienating herself from both Lily and Holden, along with most of Oakdale.

Later, Molly wrote a romance novel, thinly disguising her characters as herself, Holden and Lily. Lilly's mother, Lucinda, put a stop to it and agreed to finance the broke Ms. Conlan if she finagled her way into David Stenbeck's life to spy on him. Molly began to fall for Stenbeck, but her fear of Lucinda, and greed for material goods, kept her from telling him the truth. David found out and cruelly dumped her at the altar, shortly before his death. Lucinda dumped her too, leaving her broke and despondent. Kim Hughes took Molly into the Hughes home, but things didn't work out very well. Molly eventually got a job from Kim and began to become attached to Kim's son, Andy. Andy and Molly became friends, bonding over their pathetic love lives. They grew closer when Molly arranged an intervention that helped Andy stop drinking.

When Molly's cousin, Carly Tenney, was scheming to get Rosanna's trust fund for her 'fifty million dollar baby', Molly secretly switched the paternity tests so that Carly's current husband, John, would be named the baby's father, thereby insuring Carly the money. At the same time, she found herself inexplicably drawn to newcomer Reid Hamilton. Molly couldn't explain her attraction to him, but couldn't stay away from him either. Molly's world came crashing down around her as Brad Snyder revealed her paternity switch to the entire town. At the same time, Molly figured out that Reid was really David Stenbeck. He had kidnapped Lily and Holden's daughter and was adamant that he would raise her. Molly eventually helped Lily and Holden get their daughter back, and once again became the town pariah. Andy and his family washed their hands of Molly, and she finally washed hers of David. She moved across Oakdale Court into his old apartment, and talked Jake McKinnon into giving her a job at The City Times. Meanwhile, Molly found herself sexually attracted to Chris, Andy's beefy teenage brother. That sexual attraction led to a full-fledged affair rather quickly. Molly put a stop to the affair, though when she learned that her daughter was asking about her. Knowing that she would never be allowed to meet her daughter if word got out about her affair with Chris, she ended it.

Molly finally did get to meet her daughter, Abigail, and was ecstatic when the girl's parents let her stay in Oakdale while they moved to Saudi Arabia. Desperate not to lose her daughter a second time, Molly was determined to keep her affair with Chris a secret and keep him away from Abigail at any cost. Unfortunately for Molly, Abigail found herself attracted to Chris, and to Molly's horror, the feeling was mutual. Despite her best efforts, Molly was unable to keep her affair with Chris a secret. When the truth came out, via pictures taken by Katie Peretti and distributed by the head of WOAK's news division, Molly lost her job at WOAK. Soon after, Abigail learned the truth. Knowing that Abigail knew the truth, Chris hurriedly left town and Abigail confronted Molly. While trying to make Abigail understand about the affair, Molly lost her balance and fell down the steps of her apartment complex. After lingering in a coma for months, Molly woke up determined to correct the mistakes of her past. To buy some time, she faked amnesia and claimed to have no memory of her and Chris' affair, or of Abigail's coming to town. Remembering that the cause of all her problems was Katie, Molly decided to use her "condition" to get revenge and reclaim her life but later thought better of it. Eventually, Molly started experiencing visions of Jake's ex-wife, Vicky.

Throughout this time, Jake and Molly had become very close and Molly was afraid that the visions were a sign that Vicky did not approve to the relationship. When Vicky's mother heard of this, she visited Molly and offered the theory that maybe Vicky wasn't so much warning Molly away but trying to tell her something. Though skeptical, Jake decided to humor Molly and investigate. Through the course of the investigation, the pair fell in love and discovered a startling fact: Vicky's babies did NOT die with her in the plane crash; she gave birth before she died. Learning that the two girls were being raised by a farmer in Canada, Jake brought the girls, Michelle and Bridget, with him to Oakdale and then asked Molly to marry him.

Soon after their engagement, Molly and Jake's life started to take a tragic turn. The trouble began with the arrival of Nick Scudder, an old high school friend (and lover) of Molly's. Molly immediately distrusted Nick and warned him to stay away from Abigail. Though he seemed to be a great guy, Molly didn't trust him for a second and when the twins disappeared, she blamed Nick. However, with Nick's help the real culprit was found, the twins' nanny, Mary. Though Nick was now a hero in Abigail's eyes, Molly was still very wary of him. At the same time, while planning her wedding to Jake, Molly was dismayed when her criminal record was plastered on The City Times' webpage. Ashamed of her racy past, Molly wanted to break off her engagement to Jake, but he wouldn't let her. Instead Jake reassured her that he loved her no matter what and the two married in a beautiful ceremony at the Walsh estate. Though ecstatically happy, Molly continued to be wary of Abigail's friendship with Nick, and for good reason.

Months after her wedding, Molly found out that Abigail was planning to run off with Nick. Disgusted, Molly warned him to stay away from her daughter, which he agreed to do for a huge amount of money. Not long after, Nick was found dead and Abigail (who had since learned of Nick's deception) was found unconscious with no memory of Nick's death. Trying to protect her daughter, Molly confessed to the crime, but soon evidence came forth showing Abigail to be the prime suspect. Working with Jake to investigate Nick's death, they discovered another suspect: their former nanny, Mary, who was in love with Nick! Though Mary initially denied the charge, Abigail's memory eventually came back and, after a confrontation with Mary, she remembered that Mary was in fact the killer. Thankfully, Abigail's brother, Aaron, was on hand to hear Mary confess and the charges against Abigail were dropped. Unfortunately, the nightmare was far from over. Her secret uncovered, Mary became unhinged and took Molly hostage in exchange for $1 million dollars. Jake stormed in without police help to rescue Molly, and though he succeeded it was at the cost of his own life after he was shot wrestling a gun away from Mary. After Jake's death, his twin daughters, Bridget and Michelle were (against Molly's wishes) taken by Vicky's mother and sister to Bay City.

After grieving for Jake, Molly discovered love again with Carly's old lover, Mike Kasnoff. A sweet man, Mike helped Molly put Jake behind her and helped her move on with her life. Soon, the pair was living together. Unfortunately, Molly's trust in Mike was shattered when she learned he had a drunken one-night stand with Carly the night before her wedding. Though the pair tried to cover up the indiscretion, the truth came out that the child Carly was carrying might be Mike's. Shocked and angry, Molly moved out of Mike's house and told Carly she no longer loved her. Reeling from Mike's betrayal, Molly immediately sought comfort from new arrival Dusty Donovan. Wanting to hurt Mike and forget her pain, she let herself be seduced by Dusty and was unapologetic when Mike found them together. Though she later agreed to go back to Mike, he sensed that she wouldn't be able to accept his connection to Carly and refused. Stung, Molly continued her relationship with Dusty, that was until she realized he was scamming her for money. Months, later Molly finally reconciled with Carly and was on hand when she and Jack married again in Montana. Unfortunately, her relationship with Mike was unsalvageable and she was dismayed to see him getting closer to Katie Peretti.

Trying to move on with her life, Molly decided to enter into a partnership with Craig Montgomery and Dusty, running the club "The Metro." Having clearly forgiven him for trying to scam her, Molly became very close to Dusty, although to her irritation, he was too hung up on Rose D'Angelo. Soon, Molly agreed to help Rose's ex-fiancé, Paul Ryan, break up the couple, although she told Paul the deal was off when he got her and Dusty trapped in a locked vehicle. However, Paul's plan ended up working with Rose dumping Dusty and going back to him. Thinking she'd have her shot fat Dusty, Dusty remained obsessed with keeping Rose and Paul apart. Though she and Dusty would continue flirting and even ended up in bed together, Dusty's thoughts centered around Rose since he was convinced that Paul would hurt her. Thinking that Dusty should just let Rose make her own mistakes, Molly was deeply resentful of his concern about Rose and decided that Rose needed to be out of Dusty's life for good. Soon after, Rose ended up dead from poison and a less-than-sympathetic Molly decided to have Dusty get blamed for it.

Unfortunately, Dusty found out that Molly had tried to set him up. Although Molly tried to explain away her actions as those of a jealous lover, Dusty refused to forgive her and told her he wanted nothing whatsoever to do with her. As Dusty demanded that Molly sell her share of the Metro, Craig asked Molly to help him hide fugitive Annabelle Fettle, a baby broker who had engineered Craig's speedy adoption. Molly agreed to help Craig hide Annabelle on the condition that he tried to convince Dusty to let Molly remain a partner at Metro. However, despite his promise, Craig knew the attempt was futile and didn't even try to talk Dusty out of kicking Molly out. Later, an angry Molly called Craig and argued about their deal, with Paul overhearing about the illegal adoption! When pressed by Paul for details, Molly blabbed about the illegal adoption and Paul, in retaliation for the fact that Craig tried to set him up for Rose's murder, immediately informed the police.

Months later, Molly unwillingly got drawn into Dusty's drama again when she overheard him being threatened by a dangerous mobster named Starziak whom Dusty owed money to. Learning that Dusty was using the newly formed Rose Foundation to launder money to Starziak, Molly immediately told Holden and Lily. She'd come to regret that decision several weeks later when the Feds starting asking Molly questions about Starziak. Afraid for her life, Molly told the police nothing. Unfortunately Starziak thought otherwise and had Molly kidnapped. After spending days in a dark secluded prison, Molly was rescued by Holden and Jack. Unfortunately, she still wasn't safe. Although Holden offered to let her stay with him and Lily, Lily objected because she was afraid the mob would go after Molly. It turned out Lily was right. Now at Jack and Carly's, Molly was found by Starziak who killed the police officer guarding Molly and then tried to kill her while she was alone in the house. Luckily, before he was able to kill Molly, Jack and Carly returned home and Jack apprehended the mobster.

Although Jack intended to wait for backup before he transported Starziak, Molly was hysterical and urged him to leave immediately. Tragically, Jack and Starziak never made it to the station; Jack's car would be found in the river and Starziak was found dead. Although a search was conducted for Jack, the police could find no trace of him and he was declared dead. Heartbroken over what her hysterical behavior had done, Molly told Holden that she was making plans to leave Oakdale forever. Although Holden tried to reassure her that what happened to Jack wasn't her fault, his comforting manner resulted in them sharing a kiss. Though she pulled away, Molly felt even more guilt, which only escalated when Lily accused Molly of trying to destroy her marriage. Not wanting to cause trouble in the Snyder marriage, Molly went ahead with her decision to leave Oakdale and live with Abigail in California.

Years later, Molly had a cushy job as a news anchor in New York City and was having an affair with a very influential political figure. When the man spurned her, Molly retaliated by broadcasting his business on the air. Unfortunately, that merely served to get her fired and almost killed when her brakes failed. With help from a visiting Jack, Molly got her ex-lover to admit to tampering with her brakes. Later, Carly called Holden, who was divorced from Lily, to New York to take care of Molly Holden convinced Molly to return to Oakdale. In Oakdale, Kim offered Molly her old job back, and a furious Lily demanded that Holden keep Molly away from the kids.

Soon, Holden and Molly began investigating Meg's story that Lily's husband, Damian, had covered up the fact that, when he married Lily, he knew that Holden might not be legally dead. 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. 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 Holden's daughter, Faith, to destroy the Snyder family. Later, 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. Ultimately, Holden rescued Lily and Damian was sent to jail.

Later, Molly's old lover, Silas, returned wanting her back. Unfortunately, Silas would not take no for an answer and became dangerous. Silas coerced Molly to meet him at the Old Mill, where he got high and tried to rape her on videotape. Holden arrived in time to save her, but when Holden went to call authorities, Silas taunted Molly until she shot him dead. After the ordeal, Holden asked Molly to marry him. Unable to deal with the thought of Holden marrying Molly, Lily left town. 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.