Allowing a 14 year old to ride 23 miles, mostly in the dark, in rush hour traffic would not be the most responsible thing to do. Sorry, bassplayinbiker, but if you were my kid, you'd be known as bassplayinbusrider. No sense having two family members in the hospital.

If this is actually a 2.3 or a 2-3 mile commute then I would consider it depending on the route, neighborhood, traffic, maturity level, etc.