For British and other non-U.S. readers, American high school consists of the last four years (grades 9-12) of schooling before students go on to either jobs or university education. A high school sophomore is generally 15-16 years old. Also, the terms "prep school", "private school" and "boarding school" all have connotations of being snobby schools intended for privileged children. "Public school" on the other hand is for everyone.
The details about Chandler's camp girlfriend come from episode 706, TOW The Nap Partners. The (sketchy) details about Angela Delvecchio come from the episodes 105, 112, and 406.
During his sophomore year, Chandler Bing got transferred to a new high school. It wasn't that his mom had finally listened to his pleas to get him out of that all-boys prep school in upstate New York. No, he was moving back in with his mom in New York City because she couldn't afford to send him to that boarding school anymore. Nora Tyler Bing was going through a second divorce, and had to cut back on expenses.
"I swear," Nora said to herself, "next time I'm gonna save money ahead of time and make the guy sign a prenuptial agreement."
Nora even sublet their spacious condo in uptown Manhattan and moved with Chandler across the river to a smaller apartment in Queens, because she found out that there was a more affordable boarding/day school in Queens that she could send Chandler to, but it had a long wait list for admission. So for the remainder of his sophomore year, Chandler would have to attend a public school instead.
Chandler was happy, both to be rid of his disturbingly young stepfather at last, and to once again attend a regular school filled with girls.
Chandler had hit puberty during middle school, but had little luck with girls at the time. He only got a girlfriend when he went to camp that summer and met Julie, who thought he was cute and funny. Whenever they could sneak off for a while from the camp counselors and the other kids, Chandler and Julie would hold hands and kiss and mess around like curious thirteen year olds will do. She even promised that she would be his girlfriend next summer too, if he came back to the same camp. Chandler made sure of that by whining to his mom, "You owe me, for sending me to that boys' school upstate! If I can't see girls during the year, at least let me see them during the summer!"
So Chandler and Julie reunited the next summer, and had a great time again, despite the lack of privacy. However, the third summer was different; Chandler rather ungraciously broke things off as soon as he saw that she had gained over a hundred pounds. Julie furiously avoided him for the rest of that awkward time at the camp, but often muttered to the other girls about what a jerk and a "skidmark" he was; apparently, he couldn't even take three years of a somewhat casual commitment to a summer romance.
After Julie, Chandler had to return to the prep school, where he had even less chance of getting any action with girls, but now things seemed to be turning around, and he wanted to make the most of it.
"You sure you're gonna be all right, kiddo?" Chandler's mom kissed his cheek as he started to leave for his first day at his new school. Nora Tyler Bing genuinely loved her son, though she did tend to be neglectful sometimes, as well as oblivious to how her sex life, book writing, and constant drinking embarrassed Chandler.
The problem was that Nora was still bitter about her first husband Charles coming out and leaving his family for a new, gay life in Las Vegas. Nora would never admit it to herself, let alone anyone else, but she felt somewhat insecure and wondered if somehow it was her fault that Charles had turned gay. Thus Nora needed to constantly reaffirm her sexiness by dating younger guys and jet-setting around the world to promote her romance novels. She even married that last guy because he got along reasonably well with Chandler, and she thought they could maybe have a family again. Boy, was that a mistake.
"I'll be fine, Mom!" Chandler answered. "This is what I've been asking you for, for months." Ever since he dumped Julie and missed how it felt to kiss and touch a girl.
Nora sighed. "It's just that you always hear on the news how bad the public schools are. The violence, the poor education... all the stuff that I thought a private school would protect you from."
"It can't be that bad. Look, Mom, if you can find a private school that's coed, I'd go there." He certainly would love seeing girls dressed in cute little uniforms. "But for now, a regular school is just fine with me."
Nora shrugged and gave in. "All right, we'll see how this goes. But if you meet some girl and start dating, just let me know so that I can buy you some condoms."
"Mom!" God, why did she always have to find some way to bring up sex, or other embarrassing stuff?
Nora laughed and kissed him again. "Get going before you're late for school! Bye, kiddo!"
Girls, girls everywhere! Chandler was in heaven at this new high school. Best of all, probably none of these girls had met Julie or heard her badmouth him, so he had a fair shot at making them think that he was cute and funny too. Not that Chandler consciously intended to dump any of these girls like he had Julie, but he didn't see what was wrong with moving on and finding a new, petite girlfriend. Chandler had never taken the camp fling seriously anyway; to him, it was just a chance for mutual fun and exploration. He no more thought about Julie's hurt feelings than he had thought about Susie Moss's humiliation when he lifted her skirt in that school play in the fourth grade.
Chandler was fifteen and more concerned with trying to lose his virginity, than with learning life lessons. Even just glimpsing a naked breast would be nice, for Julie had only let him grope her with clothes on.
So Chandler went through his first few classes in a daze, smiling dumbly at all the girls and trying to decide on a good joke to charm them with. Then he saw a really pretty girl named Chelsea in History class, so Chandler decided that he would strike up a conversation with her and ask her to sit with him at lunch. Unfortunately, Chelsea was sitting across the room, very close to the door, and she left class too quickly for Chandler to catch up to her.
So he went out into the hallway and looked all around for her. Then he spotted her heading toward her locker with some friends, so he rushed after her, hoping to get a moment alone with her before the next class began. But in his haste to reach the lovely Chelsea, Chandler collided with some jocks who were hanging out by their lockers.
"Hey, you klutz! What's wrong with you?"
Chandler turned and saw their angry faces. "Oh, I'm sorry. I didn't see you guys."
"How the hell do you miss all three of us?"
"And Jason's the quarterback of the football team. You could have banged up his knee!"
"I'm really sorry. I just wasn't looking."
"You bet you're sorry, you little geek!" Jason looked at Chandler appraisingly. "Hey, I don't know you. Are you that new kid with the weird name?"
Jason's friend Tony nodded. "Yeah, I saw him in English today. Chester Bing." The jocks all laughed at the name.
Chandler frowned. "It's Chandler Bing."
"Do I look like I care? New kid, you gotta learn to watch where you're going."
"Yeah, and who taught you how to dress? You look like a fag."
"Or a rich boy. We hate both."
Chandler looked down at his somewhat preppy clothes and frowned. Then he looked up again. "Look, I said I was sorry! Will you just let it go?" He started to turn and leave, hoping that Chelsea hadn't already gone away.
Tony grabbed Chandler's arm, though, and wouldn't let go. "Hey, we're not done with you."
Jason's other friend Nick knocked Chandler's books to the ground.
Chandler couldn't believe their immaturity and how easily they were amused, but he bit his lip against making some smart-aleck remark, because it wouldn't help.
"Oh you can't think of anything else to say?" Jason mocked him. "Did we hurt your feelings, wimp?"
Suddenly, some Italian-looking guy stepped forward and looked irritated. "Will you quit it? He apologized three times already! Stop being such assholes."
"Mind your own business, Tribbiani!"
"What, all three of you are gonna beat up one pale, scrawny kid? Way to prove you're tough, guys!" He rolled his eyes and gave them a sarcastic thumbs up.
Stung, and noticing how a lot of students in the halls were staring at the scene, Jason got red in the face. He was one second away from deciding to punch Tribbiani out.
"And he wouldn't even have bumped into you if you guys didn't take up half the hallway like you always do."
Scowling and slamming their lockers shut, Jason and his buddies reluctantly stormed off, muttering about how they were late for practice.
Chandler sighed and said, "Thanks, man."
"No problem." And with that, the Italian walked off, losing himself in the crowd of students again.
Chandler picked up his books and noticed that Chelsea was long gone. He sighed and hurried to his next class just as the tardy bell rang.