Don't get involved in those conversations. Hear him out and validate his feelings. Help him sort things out by gently influencing him. Perhaps instead of trying to assess what he's doing ("I feel like you want me to tell you what to do") and putting words in his mouth, reflect what he's saying back to him ("It sounds as if you're very conflicted right now.")
Focus on yourself more. Get busier doing things for yourself. If H's confused, then he can't make a clear decision now anyway, so just let him be. Just show you care by listening to him. Let him air it all out.
