Teenager iPhone usage

So I have a teenager who has an iPhone.  He is a good boy but still want to keep tabs with what he's doing on his phone and make sure that it's age appropriate.  

What kinds of things would I check for?  
Where should I look?

I've looked at his text history and browser history, but other than that don't know what to look for.  I know he has snapchat.

Any ideas would be greatly welcome.
hrolsonsAsked:
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awawadaCommented:
We installed PhoneSheriff for our daughter.

You can compare other software here:
http://cell-phone-parental-control-software-review.toptenreviews.com/
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