For some reason in high school Jason had never really been popular, and as such he always assumed people or "popular people" thought he was a looser.
He was a big guy after all, at 6'5" he was tall for any age, and he worked out a fair amount, having played soccer his whole life, but that wasn't exactly a "jock sport" like football or basket ball. He wasn't even on the school team. His father was wealthy, and in his youth had been voted the most popular kid in his school, as had his step-mother. Likely, some day, his young step-sister would as well, since she had recently made the cheer team as a freshman.
Logistically, Jason should have been a pretty popular guy.
So why wasn't Jason popular? He was unreasonably shy. People would invite him to parties, and he would freeze, and over-analyze the invitation, worry weather it was a trick, why would the person want him there, would he enjoy it? People took his silence as intentional, and before Jason would muster up the courage to respond who ever had invited him would have given up and walked away.
Another problem was that Jason was naturally intelligent. He never studied, and rarely did any homework. In class he would never take notes, instead preferring to zone out and fill his notepads with art. Regardless of how hard he would try to slack off, he almost always aced his tests. His teacher's loved him, and would try to motivate him by bragging about him to the other students, or volunteer him to explain difficult concepts to the class. Jason hated feeling like a nerd, and he hated the attention.
He was also seen as too nice. Growing up, he had always stood up for the nerds against the jocks and bullies. This wasn't actually anything to do with caring about who was in the right or wrong, the bigger kids were just more fun to fight. No one else really knew about his real motivations though.
So all through high school Jason felt like a socially awkward nerd, and as such believed everyone else did too. So one year the most popular girl in the school, Mary, said he was REALLY cute and that she had wanted him to ask her out all semester. Over her shoulder, he literally saw her popular friends laughing at them. He may have been socially awkward, but he was no bodies fool. "Good luck with that." he told her sarcastically, shaking his head and walking away. Jason may not be cool, he reasoned to himself, but he was uncool on his own terms at least, no reason for him to fall for such embarrassing and obvious trickery.
So just before he turned 18, Jason went alone to watch this movie about becoming a spy. None of his friends had wanted to see it. The lead was challenged to get information from strangers, or get invited into their homes, while revealing nothing about himself. Jason was a self proclaimed student of psychology. While he had always been awkward about assuming what others thought of him, he had grown up watching others interact, and was pretty good at understanding how others thought or felt.
Jason reasoned that with enough planning and/or practice, he should be able to be like the guy in the movie, getting into peoples heads, saying the right things, earning trust, and all the while work himself passed his own mild agoraphobia. He would never have to fear what other people thought of him if he gained some control of that opinion.
Everyday that summer after seeing the movie Jason drove to the mall. He would sit against a wall and pick someone, a married man, an older woman, a family of three, a kid his own age, and watch them as they shopped or spoke to shopkeepers, maybe listen in on a phone conversation, and once he was ready he would "run into them" and just start up a conversation. For 90 days, 3 to 8 hours a day, Jason taught himself how to speak to people. He learned how to fake confidence at first, but as his successes mounted and his failures decreased, he grew to have legitimate confidence in himself. And he started making friends. A lot of them.
By his 18th birthday, Jason felt he was finally popular. At least at the mall.
He knew almost all of the mall-rats, and everything about them, who had dated who, who used what drug, who was a virgin, who was easy, who had a rough home life, and all they knew of him was his name, and Jason loved that they didnt seem to notice that they didn't know anything about him.
When they asked why he spent so much time talking to strangers he said he was learning to be social, which they took as a joke. The mall-rats never asked more than that. He even went to several parties by the end of that summer. By that point, people he didn't even know knew him by name.
****** The Mall Rat
One such party was held in an empty vacant apartment. Someone had jimmied the door and stayed a few nights, and decided it would be a great place for a party. There wasn't any power, so there wasn't any light either. He spent an hour talking to one guy, learning every detail about the guys life, when someone asked "Is that Jason I hear." The guy Jason had been talking to said "Who the fuck is Jason?" Jason, he decided about himself, was as skilled at being social as the guy in the spy movie. He hadn't even told this guy Kyle his name, and he knew more about him than most of Kyle's personal friends.
Later that night, Kyle's girlfriend, who was one of the mall-rats Jason kind of recognized walked off down the street from the party, and Jason soon caught up to her to ask what was wrong. Since Jason knew about their relationship problems from Kyle, it was easy to get her to open up. It didn't take too much encouragement before she told him all about how her 24 year old boyfriend wanted her to give up her virginity, especially now that she was 18, and how she really loved him but was scared to do so.
So Jason told her all sorts of generic B.S., if he loves you, he will wait, don't do it until it feels right, tell him to slow down or hit the road. That kind of thing. It was certainly the opposite of what his new friend Kyle would have wanted. He was ready to dump Kat if he didn't get some ass. But that was not appropriate advise for Jason to tell the girl. Plus, she was not exactly ugly and had a great rack, so Jason as a guy was not strongly motivated to help Kyle get some ass. Jason had the 'maybe if he dumps her I can hit it' mentality.
Eventually they got back to the party, and she left with her boyfriend. Kyle seemed none to pleased that she had walked off with another guy. Jason had a "sucks for you" attitude about it. The chic had been short, had a decent rack, and a revealing top. Jason, being 6'5" had had a great view walking beside her.
Then one day the following week, out of the blue, Kat brings in a batch of homemade brownies to the mall for Jason. Jason hadn't expected that at all. To the best of his knowledge she still had a boyfriend. Still, moving on instinct, he accepted the brownies and offered her a ride home. He had learned on their walk the week before that she usually walked home, because Kyle had wrecked her car and her dad worked second shift until passed midnight.