Both had met each other by middle school, mostly due to a tutoring agreement. However, the two had bonded to be friends after spending time togehter and sharing interests. Though Peter often worries about Mikey's little hobby of filming girls in mbikinis, underwear, or even in the nude. Something of which Peter can't figure out is how he is able to film such stuff without getting caught, which Mikey always smirks and says, 'Photographer's secret'. Teh two trsut each other enough to let Peter bite the other to save his life. After his change, Mikey become's Peter's eyes and ears to the Pack, his Robin to Batman, so to speak.
The two had met before she went into her confident stage. Back then, she cosplayed as a shy nerd girl with braided hair and lensless glasses. She might have lived her life in complete normality and loneliness if she hadn’t met Mikey on her first year in high school. While being picked on by a group of 'popular' girls about her glasses, Mikey rode into the rescue to get them to leave her alone perhaps because he had similar treatment. But he promptly put his foot in his mouth by not noticing what they were picking on Kylie for, namely her lensless glasses. After she explained why she wore them, that is to make her look smarter, she asked why he had his hair in his face, which he implies that girls would go crazy for his pretty boy face, saying he wanted to be noticed more than just a pretty face.
It was this connection that provided the foundation for their relationship, as slow as it was in the beginning only speaking in the halls. At first, it was a one-sided crush, to which Mikey knew what was going on, but wasn’t sure if he should follow through it, stating it might ruin their friendship. Despite a whole year together, they grew closer throughout their freshman year and into their sophomore year.
Mikey and Kylie or “Miklie or Corxem” first met in their Freshman Year of high school. Although, she considered him to be her “kinda-sorta-boyfriend”, Mikey only considered Kylie his friend (She’s a girl and she’s my friend, but she’s not my girlfriend). Despite their platonic closeness, there have been hints that she there might be something deeper between them. There were instances where Kylie showed her attraction for Mikey and there were instances where Mikey, despite his massive denial, showed his jealous at other boy’s interest in Kylie.
But on his second Full Moon, his instincts pushed him forward, revealing to him that he loved and desired Kylie, as she did him.