“Tentative” means “not fully worked out, uncertain, or hesitant." 

Instead of assuming an expert stance, offer observations with a “beginner’s mind.” For example, say, “I’m not sure, but perhaps you worry that…”; or, “If you felt comfortable doing it, you could consider trying ….” 

Try, “You are in a tough situation"; Sounds like you’re between a rock and a hard place"; or "I’m so sorry you have to face this kind of problem right now.”

Listen. Your very presence can be a comfort to a friend. Sometimes keeping someone company while they go through their trials is a gift in itself.

Instead of giving direct advice, tell a brief story about what happened to you or someone else that could shed light on your friend’s situation.

If your friend seems to be afflicted with tunnel vision, help them expand their perspective. You could say, “There could be another way to look at this. What about…?” 

You could also expand perspective by pointing out the consequences of their actions to their future self: “This m...