When Jack first came to town, he teamed up with Alison and Jamal to try to convince Alison's grandmother Amanda Barrington that Jamal was out of Alison's life for good. Livvie was instantly smitten when she found Jack taking a moonlight swim one night. Livvie continued being friends with Chris, but found herself growing more attracted to Jack. Jack helped Livvie overcome her fear of water. Jack was angry when Chris didn't acknowledge him. Chris wasn't too happy over Jack and Livvie's budding friendship and warned Jack to steer clear of Livvie. Chris was shocked when Jack claimed he was Chris' brother. Jack filled Chris in that their mother had died when they couldn't find her medical care. Chris was skeptical of Jack's story. Chris attempted to mend fences with Jack to impress Livvie. Chris was very determined to get Jack out of town and away from Livvie. Chris framed Jack for stealing money from him hoping that would break up Jack and Livvie. Chris made a tape of Jack saying he was only using Livvie. Livvie was hurt and Jack told her he never really cared for her. While drowning their sorrows at the PC Hotel Bar, Lucy and Jack wound up going back to her place and almost making love, Kevin walked in on them and stopped them. Livvie found out about Chris' spy and his plans and tried to rekindle the flame between her and Jack. Jack and Livvie finally made love and became a couple. Recently, Jack and Livvie went camping in the woods when Jack mysteriously disappeared. Livvie, Jamal and Alison found him unconscious. He came too, but couldn't remember much about what happened. Later that night, he made wild love to Livvie. Alison teased Jack, who passionately kissed her, which Jamal and Livvie saw. At a dangerous motocross race, Alison threw away Jamal's bike keys to prevent him from racing. Zach then forced Jack to ride by holding Livvie captive. Jack found diamonds that he was smuggling diamonds, so he began tossing them out. Zach wasn't happy, so he and his gang chased Jack. Jamal was too late to stop it and Jack flew over a cliff. Jack died in Livvie's arms and the teens buried him. To cover for his disappearance, Livvie, Jamal and Alison concocted a tale that Jack stole money from the bike shop and bolted town.

While Livvie tried to get vengeance for Jack's death, she became enthralled by mysterious Caleb. Out of nowhere, Jack returned from the dead, to the joy of his friends and girlfriend. However, his short fuse and wild mood swings confused them all. Eventually, they learned that Caleb had attacked Jack one night during a camping trip, leaving him for dead. Instead, Jack survived and became a vampire. Now bloodthirsty and possessing superhuman strength, he had to discover his new life step by step, relying on Alison and Jamal for support and to help him get packets of blood. Meanwhile, Livvie was dazzled by Caleb in spite of Jack's many battles with him and demands to leave her alone, and Chris wanted to use Jack for medical experiments after discovering the irregularities in his blood. Livvie married Caleb (invalid, since the minister was already dead), with Jack finding her soon after. When Caleb asked Livvie to kill Jack, something snapped in her, and her and Jack ran off together. The triangle culminated on the hospital roof, as Jack threw Caleb off the hospital roof, Caleb tried to strangle Jack, and Caleb's split personality Michael caused lightning to vaporize Caleb. Now a normal human again, Jack planned to go on a trip with Livvie. Suddenly his vampiric powers returned. Just as suddenly, they vanished again. This was only the beginning of 3 months of confusion and torment. Caleb lured Livvie to the catacombs, mentally enslaving her to return him to corporeal form. He used her to split the couples of the town apart, their negative energy feeding him. She began having blackouts, vanishing for long periods of time. During one of these blackouts Jack caught her in bed with an acquaintance of hers, Kyle, at the moment Jack planned to propose marriage. Jack punched him, Kyle hit his head against the wall, and Jack was briefly arrested. Jack and Livvie took a break from each other. Jack eventually learned of Caleb's revival, only to be imprisoned by Caleb. He broke out, making it to Tempted just in time to see Caleb about to kill everyone. To everyone's shock, Caleb's consort Livvie staked him in the heart. Livvie explained she had broken free of his control, but had a plan with Lucy to trick him into letting his guard down. She then admitted that she had been responsible for the manipulations which had broke up so many couples. Jack needed time to get over her actions. Then, in December 2001, angelic Rafe (on a mission to unite the separated pairs) trapped Jack and Livvie in a home that was about to be sold. They had it out, and reconciled, buying the house from the original owners and moving in.

During 'Secrets,' Jack's story involved desperately working to reclaim his best friend Jamal back from the dark side he had settled in after breaking up with Alison. Fortunately, Jack succeeded. Jack also helped scheming brother Chris dig up dirt on nemesis Amy Stradling/Harris.

In April 2002, Jack made inroads with Chris, comforting him after Eve Lambert's death. He then began developing photos he'd taken with an old camera belonging to Alison's ancestor, Rebecca. He repeatedly saw images of Rebecca in new photos, but she faded away each time. Meanwhile, Livvie became increasingly wigged out after Eve's death and lighting one of Rebecca's enchanted candles (marked TROUBLE), and was convinced Jack cared more for Alison than for her. After throwing the candle in the fire, she crossed over to the dark side. Desperate to prove the candles were a menace, she dipped a WARMTH candle in hallucinogens. Jack lit it and imagined being covered by bugs. After Kevin disappeared, Livvie went on a witch hunt to implicate Alison in his "death". When the police were about to arrest Alison, Jamal and Jack tried to help her escape through the back door of Jack and Livvie's place. Livvie blocked their way. Not only was she happy to see Ali being arrested, she told Jack that she blamed him as much as Ali for Kevin's death. Jack finally had enough, and told her he didn't recognize her anymore. She dumped him, and spurned his later attempts to get through to her. Giving up on Livvie, he began working with Jamal full-time on clearing Alison of murder charges.