If you are a young, single person, here’s some advice to you: don’t hit on food service workers while they’re at work. Your server, your bartender, your barista – be polite, but don’t try to take it any further than that.
Let’s take a step back and look at the larger case here, and then we’ll come back to that specific advice as an example. In general, you want people to be honest with you. Your life is better if everyone gives it to you straight, trust me. But honesty is not just a matter of the character of other people – you also can create the conditions for both honesty and dishonesty in how you conduct your own affairs.
Let’s take an extreme example. Point a gun at someone and ask them if they like your haircut. You’re very likely to get enthusiastic approval, but how much could you trust it? The person was backed into a corner, given very little choice but to give you the answer you wanted. Even if they genuinely liked your haircut anyway, you put them in a position where the statement is meaningless.
Now, hopefully you abstain from pointing guns at people – and hopefully you don’t abstain from such behavior just because it benefits you to do so! People deserve respect and that’s reason enough not to “corner” them. But often we corner people without realizing it (it’s not always as obvious as a pointed pistol!) and thus we often build a Liar’s Hall around ourselves without even knowing it.
So let’s get back to the friendly barista at your local coffee shop. Here’s the thing – their job is customer service. They’re at their most nice to begin with, and some of it at least is probably artificial, so right off the bat you’re probably over-estimating how interested they might be. But beyond that, they’re also implicitly cornered – they can’t just leave, they can’t just ignore you, and at least some part of them has to worry that rejecting your advances will result in trouble for them professionally. That means if you hit on someone in that environment, you’re creating the conditions to be lied to. You should avoid this purely out of respect for the other person, but the side benefit to acting honorably is that you also excuse yourself from the Liar’s Hall.
People inadvertently enter the Liar’s Hall all the time, and smart people always look for the exits. Company and political leaders who exercise a lot of power are almost always trapped there, which is why it’s so important for them to find ways to get honesty regardless.
Always be aware of when you might find yourself in the Liar’s Hall. Whenever you ask for other people’s opinions, make sure you note any reasons they may have to feel like they must lie to you, and diffuse those reasons to the best of your ability.
Personally, I have to navigate this almost every day. People literally pay me for my advice. On the one hand, they’re paying me to give them feedback they couldn’t receive anywhere else, but on the other hand, they are paying me. I learned very early that I have to set the expectation with my clients that I’m going to be brutally honest with them and not sugar-coat things, even if they get information they don’t want to hear. I don’t want them to be in the Liar’s Hall, so I make sure right from the start that I set the groundwork for honesty.
If you frequently give or solicit opinions, you should do the same.