Ask him questions about how he’s doing. “You’ve seemed a little off lately. Everything OK?” “You’ve been really quiet today. Is something going on? Anything you wanna talk about?” Empathize without making him feel bad for feeling a certain way. “That really sucks. Sorry you’re going through that.” “That can’t feel good.” “I’d have a hard time with that too.” Lighten the mood, if it seems appropriate. “Well, at least you have me to get you through it!” “Luckily we have a million tests coming up to get your mind off of it. I bet that’s really helpful, right?” Offer solutions. “Well, I can come with you to talk to her, if you want. I don’t mind.” “Have you thought about talking to anyone about it?” “I’m having trouble in that class too. Wanna study together?”