High School Senior Joey Lupo started dating Tammy Winslow in the summer of 2003. Tammy's mother, Cassie, was convinced that Joey was a troublemaker, and was shocked when the "Mother's grapevine" reported back that he was an excellent student and had no marks against him. In addition to getting to know Tammy better, Joey also became friends with her friend, Lizzie Spaulding. Although Lizzie, who was under house arrest, used Joey by manipulating him into driving her to Olivia Spencer's place, he didn't hold that against her and continued to befriend her. Late that year, Joey and Tammy were arrested when they accidentally trespassed on private property. Thankfully, Cassie's boyfriend, Edmund, was able to get the charges dropped, to the relief of Joey's mother, who was furious at her son for getting into trouble. Though Tammy appeared to be happy with Joey, by year's end, it was becoming apparent that she wanted a boyfriend who was more sophisticated; someone who was more like Edmund. Tammy's relationship with Joey continued into 2004, yet she was still unsatisfied. Though still dating Joey, she was continually exasperated by his inability to live up to the romance and passion she found in Romeo & Juliet. As for Joey, although he cared for Tammy, even giving her his high school ring, he was exasperated that she was trying to turn him into someone he wasn't. In an effort to show Tammy some romance, Joey planned to serenade her in front of the entire crowed at the party to celebrate the success of the school's production of "Romeo & Juliet." Unfortunately, Tammy, without a word, suddenly left the party, never knowing what Joey did for her. Days later, Tammy suddenly holed herself in her room, with no explanation. Although she admitted to having a fight with her mother, she refused to give any explanation for what the argument was about. Confused about what was going on with Tammy, Joey continued to befriend Lizzie who seemed supportive and encouraged him to be understanding of Tammy.

Joey soon realized how angry Tammy was when, one day, she suggested they skip school and "run off" together. After being reassured that they weren't actually running away, only laying low for a few hours, Joey agreed and he and Tammy spent a romantic day alone at the Bauer cabin. Weeks later, as his relationship with Tammy seemed more secure than ever, Joey was thrown for a loop when Lizzie revealed what Tammy had been upset about earlier---the night of the play, she'd kissed Edmund. Disgusted and angry, since he'd known she wanted him to be like Edmund, Joey broke it off with Tammy by telling her that he finally realized that she wasn't good enough for him.

With that, Joey started spending more and more time with Lizzie, who encouraged him in his goals for the future. Seeing that Lizzie was trying too hard to make him like her, Joey assured her that he did, although it was evident he meant it in a platonic way. When Joey considered dropping out of the Spaulding intern contest (where he was a partner with Lizzie), Lizzie tried to convince him that the prize was too important--he had the opportunity to win a college scholarship and an internship. However, Joey was a lot more pragmatic that the wealthy Lizzie and realized that he needed money now, not just a chance to get money. Although Lizzie promised him a job as the Spaulding pool boy (despite his lack of experience), Joey went for a better job--working at the Jessup farm where Tammy lived. Just when it seemed that Tammy and Joey are moving toward reconciliation, an unfortunate mishap (unintentionally set into motion by Lizzie) reminded Joey that he will never be equal to Edmund in Tammy's eyes, and so Joey asked Lizzie to the summer dance. At the dance though, Tammy arranged for her and Joey to share a dance.

Again, Joey started to soften toward Tammy, but the moment was broken by Lizzie, who was supposedly attacked (she faked it) and had to be taken home. At home, although Lizzie failed in her efforts to take Joey's mind off of Tammy, she succeeded in turning him against her by showing him the tape of Tammy railing against him. Finally convinced that Tammy was the wrong girl for him, Joey kissed Lizzie. Soon after, Joey was surprised when Lizzie offered to help him in his dream of a music career by giving a record executive a tape of his music. However, although he did like Lizzie, it was clear that Joey's heart belonged to Tammy. Late that summer when Joey learned that Tammy's mom, Cassie, was being stalked; he decided to stick around Tammy in order to protect her. By summer's end, Joey and Tammy had grown closer, and when Joey ended up winning the Spaulding intern contest, it was Tammy, not Lizzie he wanted to celebrate with. Although Joey and Tammy made plans to meet at the Beacon, and make love for the first time, Joey was called away with news that he had to meet with Spaulding executives that night.

With a heavy heart, Joey went to the meeting and was shocked to find himself alone with Lizzie in the hotel room. Lizzie declared her love for Joey, forcing Joey to tell her that he and Tammy had gotten back together. Feigning acceptance, Lizzie offered Joey a celebratory drink. The next morning, Joey woke up in bed next to Lizzie! Although Lizzie told him they'd made love, Joey had no memory of it. Soon the guilt got to Joey, and when he was confronted by Tammy, Joey confessed the truth about that night to a devastated Tammy. Mere days later, Joey overheard Lizzie talking to someone named JB about a drug and put two and two together--he didn't remember making love to Lizzie because she drugged him! His suspicions were confirmed when he looked into JB's bag and saw a vial with a drug. Incensed, Joey confronted Lizzie about what she'd done. Backed into a corner, Lizzie was forced to admit it which led a disgusted Joey to announce that he could never love her and walk away.

Unfortunately for Joey, his life would be changed forever when Lizzie went to her father, Phillip, the president of Spaulding Enterprises. Summoned to meet with Phillip, Joey told him what Lizzie had done, but to his surprise, Phillip sided with Lizzie and blackmailed Joey into leaving town. He also threatened Joey that if he told anyone what Lizzie had done, Phillip would force Joey's mother out of her home. That same day, Joey went to see Tammy who was ready to forgive him if he confirmed for her that Lizzie somehow manipulated Joey into going to bed with her. Fear for his mother caused Joey to keep his silence and, instead, he cruelly told Tammy that he wanted to make love to Lizzie and lied about not remembering anything about it. After telling a distraught Tammy that they weren't meant to be, Joey left Springfield for Boston University.

A few years later, in 2006, Joey returned to see Tammy. He finally told her all about Phillip's blackmail which forced him to leave. He then told her that he'd heard about Phillip's death but, by that time, he'd heard that Tammy was happily involved with another guy. Now face to face with Tammy, Joey realized that she wasn't very happy. Seeing a chance to get back what was lost, Joey proclaimed his love for Tammy and his wish that they could begin anew. Although Tammy did agree to have dinner with him, it was clear her thoughts were elsewhere and she ended things before they even began.