Earlier quoted context omitted.
> The central problem here is trust: either your kid trusts you enough to discuss things with you, or they don't. I don't think it's that simple. A predator can catfish as a high school girl, send raunchy texts and images to the boy, and the boy might be tempted to engage but wouldn't tell their parents out of embarassment (just like how a teenage boy isn't going to tell their parents about their porn watching habits…
The solution to that isn't tapping your boy's IM and chat history though. It's having a relationship with him where he feels comfortable mentioning he's talking to someone new.
1) make that communication remain innocuous long enough to fall into background ignore status
2) escalate in a way that will either avoid communicatong with you or even better seem fine to the child but not to you and so invoke the "my parent isn't fair" response and stop consulting you wholesale