As a father I worry about when my girls hit the dating age..young guys are all about it. It really depends on the individual and the parenting time that went into his thick, chick craving mind. I would worry about a young woman trying to date a guy who can't even go to the club with her. Maybe she just wants a fwb thing?
As far as the school thing..I know you are not silly enough to think he is still a virgin right? Let say he is...when he gets to college and you can't be there to babysit him..you think he's gonna leave the drunk horny campus girls alone?
When it comes down to it bro, all you can do is tell him your opinion, give him very specific reasons on how you came to those conclusions and hope he makes the right choice. He is at an age where you really don't have much control anyhow, especially if there is good cop / bad cop going on with the parents. He will side with which ever one makes him feel better about his OWN descision. If it were me, I would also sit down with his mother (and hide the "i want to choke the life out of you" tendencies) and explain your side and ask for backup.
He'll more than likely go for it. I would be more scared of him getting her prego then having to work to support the kid vs going to school....but that can happen with any girl he dates now or later in life. It's up to him to be safe and smart about it.
Good luck.
