“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.”

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 you feel compelled to give direct advice, do it. 

Some friends truly want and need to hear your opinion. Honest feedback, even when it may be hard to hear, can be just the tonic they need. Emphasize that your friend can take your advice or leave it.

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...