Let him take the lead. 

But you can say, even by text, “Hey, no pressure, but if you ever want to talk about big stuff, sad stuff, or any kind of important stuff, I am here to listen. There is no need to say anything at all, but listening is something I happen to be good at.”

I’m sure he’ll nod or say something like “OK.” Then, maybe at some point later, when a more devastating or confusing thought crosses his mind, he might introduce a more significant conversation.

After my first breakup or two, I needed to be busy. I required a packed calendar – events I knew would involve company. Sometimes hanging out and doing nothing with someone is the best kind of support.

Also know: when he does open up, you don’t have to tell him what to do, offer platitudes, or assure him that high school relationships aren’t built to last. Instead, ask a lot of questions about how he feels, what he wants now, and what he’s excited about. Admit what you don’t know. You don’t have to fix anything.