How can I know when its okay to be brutally and completely honest and when I should be more "gentle" expressing my thoughts?

Well, first of all I'd like to say you should never be afraid to speak your mind. Your individual voice matters immensely. It also shows that you are naturally a sensitive, yet honest person since you even thought to ask this question. Perhaps, it is best to be gentle when a person is in a sensitive state already, but remember the truth hurts everyone but it also helps everyone. So even if there are times when you need to phrase is more subtly because of somebody's fragile emotional state, don't worry about how their emotions might be hurt too much because ultimately it will help them greatly .

I think you should alway be honest. But, you can be totally honest and gentle at the same time! Personnaly, I would prefer to someone who is brutally honest and tell me directly ''Nah I don't like what you do'' (for an exemple) than someone who say ''well it's not bad but it's not my kind of thing'' (when s/he actually think it's bad) I hope it helped you! :)

Its always based on your senses. If you sense that there is tension and it is not the right time then don't be brutally honest but when you sense that the person that you are talking to are more open and willing to receive fed backs then be brutally honest.

From my personal experience, i would rather the other person tell me the truth no matter how much it hurts me because it is better to be told the truth (it is easier to process most of the time and to work through) than to be lied to because then you are left wondering why you weren't good enough for the truth. I would follow the other persons lead, and you will know when the time is right on how to approach the topic.

It truly depends on the person you are speaking to and you usually can kind of guess how to handle the situation based on your knowledge about the person but if you are unsure try to think if the person can handle brutal honesty if the situation is better handled with tact etc.

In m opinion, you should never be sorry for how you feel. You should however be mindful with the way you express yourself if it has the ability to hurt somebody. You should never say something with the intent of being hurtful, for example, you could say something brutally honest that might not necessarily be what the other wants to hear, but if your intentions are good, I see nothing wrong with being brutally honest. I may be taken back when someone expresses themselves in that way, but if I know their intentions are good, I end up appreciating it in the long run.

When someone asks me to be honest with them then I should be brutally and completely honest with them. If there really sad or feel very flexiable then maybe I will me really gentle.

Well communication never hurt anyone. Asking can help to figure out what to do. also reading the situation and the person will help too

I feel like this depends on the person we are being honest too. If you know they are sensitive, then use more light wording and suggestions. Complete honesty is only for the most steel-hearted.

It's on the feel, if you feel like you trust that person to see your full brutal expression, then it's maybe because you feel like they are actually paying attention to what you're saying and thus you wouldn't mind adding more details. The truth is, it's also about you in the end, you dont want to trigger yourself either, so it's important to be gentle with yourself :)