It’s never been easy to be a teenager. It’s a time of life when kids navigate a world of tough academics and complex friendships and romantic relationships.

But an app that’s taking the high school by storm this school year is making it even more difficult to be a teen., a website and online application that allows users to ask each other questions anonymously, was launched in 2010. It arrived on the Island late this summer through Twitter, just in time to greet the first day of school.

That’s when Amy Lilavois, school adjustment counselor at the regional high school, heard about the Latvian social networking site, from a junior at the school.

“I didn’t know about the site until she came in and told me, and said, this is something you are going to be dealing with,” Ms. Lilavois said. Sure enough, they began hearing of incidents of bullying on the site from some students. Students reported that their friends had been ridiculed and insulted on the site, and often felt powerless to make the cruelty stop. Shielded by anonymity, students can tear each other apart on Ask without visible consequence.

“I also have had kids who don’t even have an account and questions have been asked about them,” Ms. Lilavois said. “And their friends might be defending them but they still find out, and are devastated by what is being said.”

Two regional high school students, one sophomore and one junior, agreed on condition of anonymity to share their experiences with the site. The school feared that students, if named, might become the victims of backlash from their schoolmates.

Both students have profiles on Ask, though they know it’s a dangerous place to be. They’ve seen all kinds of shocking things posted there, they say, from rumor-spreading to cruel gossip to photographs of their schoolmates engaging in self-harm.

Most shocking to the junior year student were postings on a profile that said things such as, “You should kill yourself.”

“And some people really do take that stuff to heart, and they shouldn’t because it’s completely and totally irrelevant, but they do,” the student said.

Sitting across from her in the guidance department, a sophomore girl nodded in understanding. “Sometimes they’ll respond to questions showing a picture of the self-harm they did to themselves,” the sophomore girl said. “Seeing, like, close friends you thought were really happy and you have so much fun with, and you realize they feel so bad because they are getting all this hate and they are doing just horrible things to themselves, and just don’t want to be out in the world.”

Many comments she saw referenced specific scenarios that happened during the school day or things that happened over the weekend, the sophomore said.

“Like someone was looking behind your shoulder and looking into your life,” the junior said.

The site has received international attention in recent months, in conjunction with the recent suicides of several United Kingdom adolescents as well as the death of Rebecca Sedwick, a 14-year-old Florida girl who jumped to her death in September.

The site’s anonymity makes hurtful behavior tough to address, frustrating the guidance department.

“I have a student coming to me several times and crying about the mean things that were said about her,” said Alli Ritts, a social worker and guidance counselor at the school. “They were calling her fat, calling her a whore.”

But the bully remained anonymous throughout. Though enough specifics were given to identify the user as a schoolmate, it was impossible to confirm who the person was.

“It is hurtful and very personal,” Ms. Ritts said. “And then you get people who probably don’t know her and are commenting on it and don’t know how hurtful . . . that there’s this little girl sitting on the other end of this being harassed by someone she doesn’t know.”

The sophomore originally signed onto the site because others were doing it. “Kids join because they think, maybe I won’t get a mean comment,” she said. But it seems no one is immune from abuse on Ask.

“You want to stick up for yourself and say, that’s not true, but I think everybody cares about everybody’s opinion,” the sophomore said. Sometimes kids stick up for each other and try to dispute mean things another user has posted on their profile.

Students will publish lists of the most attractive boys and girls at the school, and those who are left off end up hurt. “Girls take it so serious if they are not on that list,” the sophomore said.

While guys also get hate on the site, they said, they don’t seem to be as affected by it.

Research indicates that girls are more likely to engage in cyber-bullying, but both girls and boys can be victimized online.

“That’s what girls live off of, the drama,” the junior said. ”Guys can just be in a fight and punch each other, and girls don’t really operate like that.”

Teenagers’ attraction to drama is expected developmentally, the counselors said, but the use of social media “makes it a lot easier to say what you want to say without consequence,” Ms. Lilavois said. Ask’s anonymity capabilities make it even easier to disconnect from the damage caused.

Lately some students’ Ask profiles are concerned with homecoming, who is going, who voted for whom for king and queen. The students say the use of the site is not all bad, and sometime secret admirers even post nice things on a user’s profile. But while some questions are benign and even friendly — How are you? What’s your favorite color? — language is often crude and direct, even explicit. It’s also possible that the ugliest behavior the site produces is invisible to most. Questions received to an account are not public until the user publishes them on their profile, so the worst insults and rumor-spreading likely goes unseen.

While commentary could be posted to a profile by anyone worldwide, many of the hurtful words are specific enough to identify their source as a student at the regional high school, they said. But identifying the person further is basically impossible. This leads kids to question even their most trusted alliances, the girls said.

“If somebody hates you in person, you know it’s that person,” the sophomore said. “But if you don’t know who it is, you just start questioning everyone around you.”

“You start questioning your relationships, which is not something these kids should have to add to their lives; they are stressing about enough things,” Ms. Lilavois said.

Ask, Twitter and Instagram, the social media of choice at the regional high school, have replaced other sites that older generations have begun to master. Facebook is now for older users, both students agreed. “I am friends with my Dad on Facebook,” the junior said. “My family can go on and see my pictures.”

The girls think that most high school parents don’t know their kids are using Ask. They probably don’t even know the site exists, they said. Just as parents grow familiar with Facebook and Twitter, new technology has emerged that’s totally unfamiliar to them.

“The younger adults seem to know what’s coming up before we do,” said assistant Cape and Islands district attorney Eileen Moriarty, who travels the region speaking with kids and adults about safe internet use.

When cyber aggression was apparent on Facebook, investigating the incident at the high school was simpler. They knew who to call in for questioning. With Ask, a user identified as “anon” could be anyone — including the profile owner himself or herself.

“Who knows who it is, it could be anyone,” Ms. Ritts said.“It could be one of 100 kids.”

In the case of the student who approached her in tears, guidance advised her to delete the app from her phone. But she ended up downloading it again, only to confront another barrage of cruel commentary.

“If kids come to us, we offer the support that we can, but as far as getting it to stop . . . if it was Facebook or Twitter we’d get it to stop right away. And we have done that in the past, we’ve had kids take down their profiles,” Ms. Lilavois said.

The counselors report all incidents to the administration, but often their hands are tied.

“Our power as faculty members is pretty much taken away because it’s anonymous and we don’t know who to deal with,” Ms. Lilavois said.

Ms. Ritts said she suspects that some of the students engaging in callous online bullying activities are not your typical high school aggressors. “It’s anonymous and they can say what they want to say,” she said.

The counselors say they are equally concerned for the bully as they are for the victim.

It takes about one minute to create a profile on Ask. Once you have a profile, you can view the profile of anyone in the world with an Ask account. You need not make contact with the user in order to read the postings on their page, unlike the friending system on Facebook.

Ask provides no mechanism to disable accounts, so once a profile has been created, it will never go away. This is why Eileen Moriarty tries to drill the dangers into kids’ brains.

“We tell the kids they shouldn’t ever post anything online they wouldn’t want to see posted on a billboard,” she said.

Users on Ask can change the privacy settings to disallow anonymous postings. Users can also add other users to their blacklist, to block posting capabilities. But girls say many people don’t know they can switch their settings.

The high school blocked access to the site through wireless connection, but students can still log on with their smart phone apps using a data plan. The sophomore said she has frequently observed fellow students logging onto the site at school.

At a November schoolwide bullying prevention assembly, high school guidance counselors plan to discuss Ask with the students.

They also plan to correspond with parents to alert them to the misuse of the site. The high schoolers suggested that Ask become a topic of discussion in advisory groups.

All Island schools have a bullying prevention plan mandated by the governor’s signed anti-bullying act of 2010. Cyber-bullying, under the legislation, is defined as bullying using online or electronic communication, and includes the impersonation of another person on social media.

Island elementary schools have addressed cyber-bullying via school-wide initiatives but have seen few cyber-bullying incidents surface at school. Their focus has instead been on awareness. This month, the Edgartown School held a cyber-bullying event for parents, where Jeanine Fitzgerald, a bullying expert, came to speak for the second year. “This year we really wanted to target cyber-bullying because that is probably the most popular form of bullying,” said principal John Stevens.

“It is unfortunate that electronic communication is the conveyor to cyber-bullying,” he said. “It is one of the ill effects of technology.”

He said most of his middle school students have smart phones.

While the school has not dealt with any specific cyber-bullying issues in the past, he said they are trying to stay ahead of the curve.

“If you really inform parents of the potential of electronic communications, and how parents should talk to their kids and how parents should look at their kid’s Facebook site, I think a lot of this unfortunate harassment and bullying can be prevented,” Mr. Stevens said.

But he said monitoring is more difficult when students are using technology unfamiliar to their parents. The next time Ms. Fitzgerald comes to the school, he will ask her to conduct a more hands-on lesson in which parents look at the sites, and learn about the various settings and options available to prevent bullying.

In Tisbury, parents and kids were engaged in an evening of cyber awareness training by the Cape and Islands district attorney’s office two weeks ago.

School principal John Custer said his kids don’t often volunteer information about their technology use, so it’s hard to tell what sites they are using. He first heard about Ask at the presentation last week.

Ms. Moriarty said the site is gaining popularity across the Cape this school year. “When adults were looking at it, it was very disturbing to them what they were seeing on there,” she said. “The types of questions being asked, the conversations coming out of there. We haven’t seen anything positive coming out of it.”

Her advice to parents? Monitor kids’ online activity and ask them to charge their cell phones in a communal space at home. “You have to look at the phone and see what apps are on there,” she said. “Even if the child has a phone, a parent is still a parent, and needs to look at it with more frequency.”

When dealing with cyber-bullying, Mr. Custer said it’s often hard to tell what is a school issue and what isn’t.

“Sometimes it’s gray because most of the things that we’ve had to deal with had originated outside of school but . . . when they are here, there might be reaction to or fallout from an online issue.”

Even if the initial incident may not have anything to do with school, he said his staff wants to support students whenever possible. The school employs three guidance counselors.

At the Tisbury school, the school resource officer, Scott Ogden, often assists in handling cyber-bullying incidents.

“It’s really nice to have his presence in the building, sometimes there are issues in this arena where it might not be a school issue, but we feel a need to address it and support students and families,” Mr. Custer said. He said Mr. Ogden is there to support and help kids and parents, not to punish and arrest.

He’s not sure how many of his students have smart phones because the school observes a phone use prohibition during regular hours.

“Honestly, kids are very understanding about that, and they adhere to that, they think it’s reasonable,” Mr. Custer said. “I get that many parents need kids to have their phones. It’s one of those things that we’ve had to adjust to and adapt to as we go.”

At all Island schools, students are encouraged to approach guidance counselors to speak about their experiences with cyber-aggression. More information about online bullying is available at