*A series of works written within one day
Besides philosophy, my value of honesty is most shaken in relationships, especially romantic. It's clear unapologetic honesty shouldn't be used as an excuse to avoid the responsibility of kind communication. It's clear relationships are partially based on a romantic fantasy and you shouldn't say demeaning things like "you aren't the prettiest or smartest person" despite the clear truth. While truth and honesty should be the highest values as the bedrock of trust, there is real tradeoffs to be made between honesty and its most often competing value: an optimistic kindness.
The biggest problem with truth in my estimation is it is frequently promised but rarely delivered. The appearance of truth coated in a defensive kindness can be seen as shinier then the real deal. While the truth can be grimier than a pleasant fiction, good communication and other factors outweigh it in importance. And a more honest foundation pays off longer term as most of the value of relationships are in the long term, high trust ones.
Is it true; is it kind, or is it necessary? — Socrates.
The largest gray area between honesty and kindness is how much information to share and when. Complete transparency is an impossible goal even to yourself. Some facts are basically unforgivable curses that resonate within someone and poison the goodwill of the relationship. These truths often touching insecurities should be recognized and avoided. But more unclear is when you ask someone out or early in a relationship should you acknowledge solemnly that statistically things never work and people get hurt or should you strive to make a real commitment to try something that may fall apart. Should you reveal information someone would really want to know on a first date, how about second?
The second question has a lot of ambiguity. But for the first question, I believe that the best chance of success in a romantic relationship comes from two people earnestly committing to try. They are risking something to believe in something. Til death do us part seems like an impossible commitment, but when you take the commitment seriously, not irrevocably but seriously, then you manifest and look for solutions you otherwise wouldn't consider. So I consider the romantic fantasy I mentioned earlier to be adaptive for creating something closer to an ideal relationship. Every time you perhaps aren't completely honest and say she is the most beautiful girl in the world then it becomes more true.
If you have the time, the ideal communication takes into account the other person and generously communicates the information with kindness and aims for comprehensibility and usefulness. But in tough times, you need to fall back on a layer built on trust where you need to share something real. You dont want to control someones reactions but here is something we need to deal with. Whether a disaster in life or a relationship, you need a fall back layer of real devotion to deal with issues. Its when a relationship is most at risk that you most need a strong backbone of truth underwritten with love.
Honesty in relationships is one of those things that sounds simple until you actually try it. Most of us default to softening, delaying, reshaping — not out of malice, but because the gap between what we feel and what we say has been trained into us for years. Curious how you approach that in the issue.