“Whenever you think that some situation or some person is ruining your life, it’s actually you who are ruining your life. It’s such a simple idea. Feeling like a victim is a perfectly disastrous way to make go through life.”
— Charlie Munger
Remember to $@!#% the switch when you’re stuck: If you’re all up in your head, sad or anxious, do something physical. If you’re down with a physical problem, dive into your mind for diversion and healing.
Institute a “leave by” time instead of a curfew. That way they won’t panic / speed if something out of their control happens to make them late. “Leave Riley’s house by 10pm.”
Try silence. Just sit with it (problem/feeling/etc.) invite the problem to sit next to you and just be quiet. Five minutes every day for a week or two. Your solution will appear. Stop running and just sit with it.
Sex isn’t something you “score.” It’s not a competition. Whether the encounter is casual or within a committed relationship it’s something that is shared.
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.
Keep in mind the human tendency (rightly or wrongly) to think “how it ends is how it was”.
Could be a work shift, a class, a relationship, etc. try to end on a good note.
Imagine a hundred different lives. Try a dozen of them. Fail at most of them. That’s part of what your twenties are for. Challenge yourself. Challenge your assumptions. Change your perspective. Grow.
Speak up when it’s called for: Fight injustice, stand up for others, etc. but shut the F up if you’re thinking about offering an unsolicited opinion or advice about anything you’re not personally an expert in.