Check out fencing. Local fencing club has classes for kids and adults all ages. They also do birthday parties, so that might be something different that would be fun for him and his friends.
Go to College results. Org to look at graduation rates. How likely is a rising freshman at that school to stick it out and graduate in 4 years? HUGE variation, it should factor in their decision.
Ask them “what would it take for you to_____?” (Keep your room clean, stay on top of your homework, feel like you had more control in this situation, etc.) Instead of nagging or lecturing, just ask.
Think about building a career. Take low-paying or no-paying jobs that will give you the experience you need to build it. It's not all about the paycheck, especially when you're young and don't have too many bills to pay.
Quoting Sarah Bessel: “One of the best things Jen Hatmaker has taught me about raising big kids: if they get on the roller coaster of Big Emotions, my main first job is to stay on the platform. I am NOT to get in the car and ride up
Professor Scott Galloway’s advice: Paraphrasing his standard wedding toast:
“1. Express affection and desire. Everyone wants to be wanted. It’s healthy and it is part of what makes your relationship singular.
2. Never let your wife / girlfriend be hungry or cold. Two thirds of the really awful arguments you’ll have it’s because someone is hungry or cold. Carry blankets and protein bars. (You’re welcome.)
3. Don’t keep score. Decide what kind of friend / son / daughter / spouse / employee / human being you want to be, and practice being that. Put the scorecard away.”
Have the first of many talks about what consent means. Tell them (boys AND girls) that consent needs to be informed, enthusiastic, sober, ongoing and freely given. Stress that, in no uncertain terms, the absence of consent is rape. Discuss the legal, moral and emotional consequences.