By Jeremy Sherman, Ph.D.

You may have offended your friend; you’re not sure. You feel like apologizing. But if the insult didn’t even register, then you’ll open the very can of worms you’re trying to close. Still, if your friend is offended and fuming, you’d really better fix it.

Should you say something?

Another friend is chronically ill. You want to show you care, so it feels callous to ignore it. But if your friend is just trying to get on with normal life, it might seem callous to call attention to what your friend is trying to forget.

Should you bring it up?

Mind Readers Dictionary : Play in Popup

Mind Readers Dictionary: The Podfast : Play in Popup

You and your spouse have decided to divorce. You both say you want to negotiate a fair win-win settlement, with no bad aftertaste. But as you get into it, your soon-to-be-ex starts making demands that feel like act of aggression in an all-out battle. Maybe a reminder about civil negotiation will deescalate the conflict. Or maybe instead you’ll be accused of trying to manipulate. No, maybe it would be better to highlight the problem by making equally aggressive demands. But what if that makes you the unreasonable one?

Should you bring it up, stay reasonable, or match aggressiveness?

We all face such questions. Some self-help leaders say the answers are easy and obvious: Be honest, be kind, be generous, stand up for yourself. Trouble is, the guides disagree on the easy answers.

That’s because there are no easy answers. These questions are tough judgment calls-situations in which the same action can lead to opposite results, either improving things or making them worse, and you can’t tell which in advance (see ACIDs). When the right thing to do by one interpretation is the wrong thing to do by another, there’s no sure-fire solution-and it’s not because you’re dumb or it’s someone’s fault. Tough judgment calls come with the territory of being alive.

Politicians face tough judgment calls too, starting with the two basic ways to read an election. If an election is a civilized debate designed to help people make up their minds, candidates who get too aggressive will only hurt their prospects. People expect their candidates to be moral. Candidates who underestimate the people will fail.

But if an election is an all-out fight, the candidate using the most aggressive tactics will sway the most voters and win. So you can’t afford to be reasonable. Candidates who overestimate the people invariably lose. If you’ve got to win because you’re crusading for a higher moral value, it’s actually more moral to cheat.

If it’s a civilized debate you’ll do best by being reasonable. But if it’s an all-out war you’ll do worse. Instead you’ll do best by fighting dirty. But if it’s actually a civilized debate, your dirty tricks will backfire.

In this presidential election both candidates claimed they would fight clean. Both are by now fighting dirty, though the Republicans by any neutral measure seem to be taking the lead, justified (they might argue) by a belief that it’s moral to do whatever is necessary to take America back from the dangerous liberals.

The press and the rest of us debate which candidate is fighting dirty, as though only depraved people lie or manipulate, and we sure wouldn’t want a president who would do that.

However, we all lie. That is, whether by outright false statement, distraction, or omission, we all at times encourage people to believe what is useful to us for them to believe. We like to think that presidents wouldn’t have to lie, or that they shouldn’t because the stakes are so high. But they have even more reasons to lie than the rest of us do.

The more intimate the connection, the more both costs and benefits of lying escalate. Why is it so much safer to vent your frustration at an inconsiderate driver than an inconsiderate spouse? It costs less to be honest with someone you’ll never see again. Presidents are, in a way, intimate with all of us. Power is intimate influence. They have to lie.

Who’s to blame for our political morass and the dirty politics it encourages? Well, in a way, no one. Tough judgment calls come with the territory, including the tough judgment call about whether to fight dirty.

In a way, though, we the people are to blame. We like to pretend that tough judgment calls don’t exist or that there are easy, obvious answers. We like to think politicians should know we only want straight talk. When we think like that, we’re lying about lying. We’re pretending we believe and can live by a simple rule like “honesty is the best policy.”

For a fascinating look at an attempt to win a presidential election by speaking honestly about unpalatable subjects to real people, check out the book As If We Were Grownups by Jeff Golden.