Eugene used to attend a boarding school before transferring to Midtown High School in his junior year. For a time he dated May Parker, the two met and began their relationship in the summer before their junior year, eventually the two grew more distant when May began operating as Spider-Girl again. Gene was jealous and possessive but May herself didn't notice this behaviour, the distance between them eventually led Gene to accuse her of neglecting him, failing to support him and only wanting to spend time with him when it was convenient for her and publicly broke up with her in the school hallway.
He then immediately began dating the schools mean girl Simone DeSantos who had shown previous interest in him and a dislike for May. He then later approached May while her baby brother was in the hospital and May promised to change and devote her time to him if it meant them getting back together, despite this though May found it difficult to conform to Gene's expectations and when she learned that he had been the one to graffiti her campaign posters she very publicly broke up with him in front of his football team and exposed him for being a 'selfish, insensitive, manipulative, egocentric, insecure little sick-o'.
When Gene then tried to publically accost who he thought was May but was in fact April Parker she dodged him and then threw him across a room with ease thus humiliating him even more. When Simone was later kidnapped by Fury Gene was chastised for not trying to help her and while Simone was out of school recovering he tried to hit on April Parker but was quickly stopped by May, despite her attempts to keep them away from one another he approached April again soon after seeking a date which May convinced April to blow off although he did continue approaching her afterwards and they even went on a date where Gene talked about himself and May while expecting April to watch him at the batting cages which she didn't appreciate.