Do any or all of these things (as necessary) in an order that is most natural to flow of the conversation. The first three items are especially important for open, compassionate communication. Listen to him Allow him to get anything off his chest and hear him out. “You seem upset, want to talk about it? Is there anything I can do to help?” “How are you feeling about this?” Be present with him Practice active listening, hold his hand, and/or make eye contact to show he has your full attention. “Uh huh”.... “I hear you”.... “I understand”.... “I’m here for you.” Validate his feelings Show that you are understanding and compassionate about his situation. “I’m sorry you’re going through this, hon.” “I can understand why you’re feeling upset about this.” Allow for silence Sometimes he may not be ready to open up about what’s bothering him and that’s okay. “It’s okay if you don’t want to talk about it, I’m here for you whenever you feel like Talking.” “If you need a moment to think about this, I understand.” Give him space if he needs it Some people who are upset want to be alone for a little while, so give him time to himself if he needs it. “I understand if you need some alone time. I’m here for you whenever you want to talk or if you just want a hug.” “If you need some quiet time, I’ll come back in 15 minutes to check in with you.” Encourage extra support if necessary After a while, if he starts withdrawing from friends and family, engaging in risky behaviors (or addiction), and/or showing signs of depression and anxiety, you might suggest he find more support. “I’ve noticed you’ve been really upset and withdrawn lately. Have you thought about talking to a therapist? I’d be happy to go with you too, if you want.” “I can see you’re struggling with this, do you think talking to a professional would help?”