Romeo is a man of many charms. Originally from RichmondValleys, he developed quite a reputation as a lady's man throughout his four years of high school. He probably had more notches on his bedpost in freshman year alone than his entire graduating class. However, it seemed all that was changing when he met the beautiful and innocent Jennifer Everestt in his senior year. Despite his scandalous past, Jennifer took a leap of faith and became the woman envied by everyone because she appeared to do what no one else could – hook the lothario. Her magnetic pull didn't last long, however.
Three quarters into her freshman year, Jennifer became distracted by the problems happening in her parent's marriage, which left an impatient Romeo out to stray. Unfortunately, he picked the wrong woman to screw around with – his girlfriend's aunt. When Jennifer learned of Romeo's betrayal, it was the end of their romance. Romeo then took four years to re-evaluate his choices, and survey the female market as well. In the end, he realized what his life was without her. Therefore, he decided to track her down and learned she was living in Hallandale with two male roommates, one who turned out to be Romeo's former assistant coach, Dylan McCloud. Instead of revealing himself to her, he arranged for Dylan to set the stage. Unfortunately for him, Dylan became too focused on problems in his own relationship that everything went south and Romeo had no choice, but to come out into the open. Still, Romeo did so under an air of mystery, making contact with Dylan's ex, Garrettlyn Michaels, first. After ruffling her feathers a bit, he left a message for her to convey to Jennifer. The note stumped Jennifer, but it all became perfectly clear when Dylan arranged for Jennifer to meet Romeo at the abandon labyrinth.
Coming face to face with her ex, Jennifer could not hide her contempt and disgust towards him and what he had done. Romeo, however, took it as a sign that Jennifer was still harboring unresolved feelings of passion for him. The following afternoon, he confronted her outside El Club de Moniasis, hoping to break down her defenses. Despite getting her to shed a few tears, she remained pretty vocal that all she felt for him was utter contempt. When she voiced that there was nothing he could do to validate the pain he put her through, Romeo ceased the moment with a kiss, a lock that Brian Fieldings got to witness firsthand. He then took joy in flaunting the history of their relationship to Brian, who became livid with Jennifer for standing him up for her ex.
Three days later, Brian and Jennifer aired out some of the tension lingering between them, but before he could explain his actions, Romeo came crashing in on them. Feeling quite uncomfortable, Brian quickly dashed out of the mansion, leaving Jennifer once again to deal with Romeo. The two continued to bicker over his past mistakes and despite trying to maneuver yet another kiss, his advances were soon return with a slap across the face. The following afternoon, Romeo passionately confessed to Jennifer that he wasn't giving up. Oddly enough, he managed to crack through her façade and before Jennifer knew it, they were making love in her bed. The next morning, regret came full circle as Jennifer outright informed Romeo that what happened the previous night could not happen again. Romeo, however, informed her that after last night, he wasn't giving up. Later that day, he ran into Garrett at El Club de Moniasis. Following their encounter, he overheard her speaking with Brian, who shared with Garrett his attentions on telling Jennifer how he felt first thing tomorrow. Romeo quickly reacted by setting up an evening of romance for Jennifer, who was immediately put off by his presence in her home. The evening, however, ended triumphant for Romeo, who managed to seal the deal once again with Jennifer. However, his triumph was short-lived.
The following morning, Brian discovered Jennifer coming out of the kitchen in nothing, but Romeo's shirt and was unable to contain himself. Jennifer was left with a whole slew of mixed emotions, which caused her to push Romeo away once again. Romeo's luck turned from bad to worst when Dylan discovered he lied to Jennifer about the flowers she received and threatened to tell Jennifer the truth.