The Facebook chat started out innocently enough.

First, he wanted to know if they knew one another from school, and if they were friends. Then he set up the ask.

"You can't tell anyone about this, and if you do, there will be consequences," he wrote. She asked what was wrong.

"Can u send me a pic of your boobs and

?"

Followed by: "Wanna see a pic of my

?

The 14-year-old recipient of the requests said no.

"Please," he wrote. "Pretty please."

She kept saying no.

"I'll do anything to get the pics of you naked."

She eventually pointed out that he was going out with another girl, which he acknowledged. The chat ended abruptly after that.

Bonny Ghosh, 34, the mother of the New York teen girl, discovered the conversation during a routine check of her daughter's social media and cellphone accounts. Ghosh had always made it clear to her daughter that she would periodically check in on her tech, and requests like this one have gotten surprisingly more common.

What used to be an uncomfortable conversation between parents and their children about real-life sexual activity must now include topics like digital propositions, sexting and pornography.

In fact, a child's earliest sexual encounters and exploration could very well occur online.

Ghosh first found an inappropriate request from a classmate when her daughter was in sixth grade. Since then, there have been a few instances where male users of Kik, a free texting app, have sent her daughter pictures of naked male anatomy, seeking reciprocity. Her daughter has not been enticed by any of the offers.

"There is so much emphasis that daughters should protect themselves, that they should never send a naked picture of themselves, and my daughter is savvy enough to know better," said Ghosh. But, she added, "I am wondering: Are other parents having the same conversation with their sons?" For instance, did the boy who sent her daughter the explicit request realize that she would save the messages? (In cases where she knows the student involved, Ghosh calls his parents to let them know.)

A recent viral blog post by a mother of four sparked discussion on this very issue. Kim Hall of Austin, Texas posted an open letter to her sons' female Facebook friends, warning them they will be blocked from the Hall family's sites if they post sultry selfies. Hall, who has three sons, titled the post "FYI (If You're a Teenage Girl)" and it has now been viewed more than 5 million times. Among others, it raised the question of whether parents hold their sons and daughters to the same standards when it comes to their behavior online.

For Ghosh, the messages indicated to her that it was time to have a no-holds-barred talk with her daughter about the new age of sexual activity.

She took a few weeks to think about what she wanted to say. She didn't want her daughter to feel judged or ashamed for being curious, which is normal during the teenage years. But she wanted her to understand the consequences that come with any sort of sexual activity, whether in real life or via a phone or computer.

"My fear is less about her getting pregnant. What I worry more about is her emotional well-being," she said. She brought up examples from the news and from within her daughter's social circle in which girls' reputations have been maligned by online images and rumors. They talked about the motivation behind such requests and how this kind of behavior has nothing to do with affection or love.

The boy who asked her daughter for naked pictures on Facebook turned out to provide a textbook example of the lesson Ghosh wanted to impart.

Five minutes after her daughter shot down his request, he made the exact same plea in a message to her best friend.

Thirteen-year-old Aman Chishti has figured out keys to success that people twice her age struggle to unlock.

She's turned a passion into profit.

Aman joined the school paper in fourth grade and decided the next year that she wanted to improve her skills. Online, she researched ways to become a better writer. She checked out nearly a dozen books from the public library on how to improve her craft and make it marketable.

She discovered constant-content.com, a place where writers can submit articles for purchase or respond to requests for pieces, and used her father's PayPal account to receive payments.

She sold her first piece, "A practical guide to traveling on an airplane," for around $30.

"I didn't know how to price it ... I ended up under-pricing myself a lot," she said.

I asked her how her enterprise was going.

"I'm not ever writing on spec again," she said.

"Why not?"

"Many of the assignments would fall through, and I didn't have a kill fee," she explained.

I was at least a couple decades older than her before I negotiated a kill fee. Or even knew what one was.

Aman, who lives in Ballwin, Mo., read a few more books about freelancing and decided she might have better luck pitching ideas directly to editors. She taught herself how to write cover letters and queries.

"I'm working on a story about how to deal with pre-wedding jitters," she said.

"You're 13. What do you know about pre-wedding jitters?" I asked her.

She looked at me.

"I interview people."

The future of journalism may not look so grim, after all. "I've been thinking about doing this when I grow up since I was in fifth grade," she said. In the meantime, she has won the school spelling bee every single year since fourth grade. She is saving her money to buy a better camera before she launches a lifestyle blog. She's publishing an anthology of poetry, which involves getting it copyrighted, finalizing cover art, soliciting writers and editing their pieces. She's also handling the promotion and marketing for the book, which she hopes to have ready for sale in a month.

Some level of ambition is innate. But like other personality traits, parents can play a role in nurturing or sabotaging a child's initiative. Aman's parents, who emigrated from Pakistan decades ago, said they noticed the fire in her belly when she was very young.

Aman is the eldest of three children and says her parents are supportive, but have never pushed her to pursue her entrepreneurial ambitions. They keep an eye on what she does online, but they let her do her thing.

"I don't know what to tell you about this," her father, Akbar Chishti, said. "We're glad she's motivated. ... I'm a little afraid of all the time she wants to spend on the Internet, because you have all kinds of people."

Initiative like Aman's doesn't always come naturally, even to people with 10 years on her. I've had parents of college graduates contact me and ask me to help their adult children navigate the industry. I'll tell them to pass along my phone number and email, but it's rare that they follow up and contact me themselves.

To encourage ambition, Tim Elmore, president of Growing Leaders, a nonprofit that offers leadership training and resources, suggests parents have their children specify one or two things at a time they really want to achieve.

"Narrowing focus can be especially challenging for kids with a go-getter spirit, so specific and identified goals are important. Once they identify a goal, help them create a plan to reach it," he said. Also, establish rewards that only come as they demonstrate progress. "This will help separate the idea of 'showing up to lessons each week' from 'putting out effort and practicing on their own time' -- the way goals are actually met and exceeded," he added.

Elmore says well-intentioned parents can end up undermining a child's ambition.

"I think this generation of kids, more than any before, are most susceptible to having their ambition undermined by truly caring, well-intentioned adults. We don't want to see our kids fail, so we think doing things for them will prevent that. But that sends an even more insidious message: 'You aren't capable of doing anything.'"

Aman doesn't bring up her age in her queries because she knows most editors wouldn't take her seriously. But if she needs to sign a contract, she'll have her parents do it and explain why.

"I prefer to let my writing skills speak for themselves," she said. The real-life experience has given her a wisdom beyond her 13 years.

"I learned that there's no way to start out perfect, and not even good, honestly," Aman said. And even though she's managed to make several hundred dollars from her writing projects so far, she's figured out that most writers aren't in it for the money.

"I've learned the only reason you should write is because you love to write."

She has set her sights on writing a novel during National Novel Writing Month this November.

And she's already heard from her mother a refrain that generations of Asian American children have heard prior.

"I told her I want her to write like a hobby, not a profession," Unsa Chishti said.

"I'd like her to be a doctor."

When a former Disney child star gets nasty, it's bound to draw some attention.

When that star is Miley Cyrus, the Internet can chatter of little else for days.

Her infamous performance on MTV's Video Music Awards featured her dancing in a teddy bear-adorned teddie, tongue hanging out, before stripping down to nude undies and gesturing unsubtly with a large foam finger. She shared the stage in a memorable fashion (as in, hard to unsee) with musician Robin Thicke, who sang part of his "Blurred Lines" summer hit.

Besides out-of-touch grown-ups having to explain "twerking" to one another, why does Miley push our buttons so? After all, the VMA stage is where Madonna and Britney Spears shared their open-mouth kiss years ago. It's where celebrities actively try to provoke us.

And Miley was trying so hard.

She's one of the most commercially successful child stars born of the Disney machine. The merchandising, movies and platinum albums have made her one of the richest young celebrities, worth an estimated $120 million.

Thicke's hit was an apt anthem for Miley. She's been blurring the lines between girl and woman for a while now. For those whose children discovered her when she was 12 years old and playing Hannah Montana, her public transformation has been rocky. The road from wholesome to whorish will have some awkward turns.

And awards shows have become modern-day morality plays.

The commercials during the Super Bowl; the jokes, outfits and snubs during Hollywood's awards season; the over-the-top performances at the VMAs: These are the cultural touch points that give the rest of us a chance to bestow our approval or bellow our outrage.

When performers push the envelope, the collective pushback is a societal indignation reset button. Clearly, she pushed too far. If there are standards of taste and acceptable public behavior we wish to impart, the widespread mockery of Miley offered tweens and teens a textbook lesson in what not to do. Parents who made the questionable decision to watch the show live with young children may have had to flip the channel or endure an embarrassing moment.

Asking a young viewer, "Why do you think she wanted to perform that way?" might lead to an interesting conversation. Shocking an audience with a tawdry show is not the only way to garner attention. Perhaps Miley sees it as her only way.

At the end of the day, Miley's goal is to sell more stuff. Whether or not this stunt helps or hurts that cause has yet to be determined. But it's a good reminder to parents that pop culture icons are never reliable role models for our children. Even the Disney-scrubbed versions grow up and struggle to define themselves.

Her spectacle also raised the question of whether we would be as scandalized by a young male star performing as suggestively. Both male and female stars have used their sexuality as a blunt object. If the reaction was any harsher because of her gender, it's largely because the performance failed.

In that blurred space between sexy and vulgar, she gyrated her way into the latter. In the blurred space between provocative and pitiful, she left the audience feeling a little sorry for her.