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If the site feels it has grounds to do that based on her report to them then should he be concerned about going to jail like she said?
Cybersex with a minor is illegal, even without exchanging pictures or meeting.
He flirted with her for a bit by calling her pretty and kissed her cheek online but nothing else happened. There was no nudes pictures or anything of that nature nor did any party try to coerce the other to meet publicly.
While he was talking to this girl, another girl shows up on a different chat calling herself, blackmail.
If the conversations are 100% innocent, there is nothing to worry about.
With that said, it's probably in your friend's best interests to avoid chatting with underage women in the future.
Anyways he tells her he has to leave but then she invites him on chat step under the same room that blackmail had setup. Again nothing happened but she started to say how she had screen shots of their conversations and threatened to have him prosecuted as a sex offender.
Blackmail kept inviting him to join her in chat step and every time they did, some random person would show up that she didn't invite but accused him of inviting them anyway.