Occasionally, I see advice on G@G to "just be yourself". I have given that advice from time to time. But I only give it in certain contexts. It's not particularly good advice in many social settings. For example, few teachers will tolerate students who regularly act according to how they see themselves. Likewise, being yourself is not appropriate in most working situations Usually, you are hired to be who they want you to be, not who you actually are. So when is it good advice to be yourself?
First, let me define what I mean by being yourself. I don't see it as being selfish, rude or hurtful. Some people say awful things to others, and then attempt to justify this by claiming they are just being honest or expressing themselves. That's just an excuse; it was never about themselves. Instead, I see being yourself as being open, in word and deed, about who you are with another person. The question I see is how open should you be with someone who doesn't know you?
On this site, the question most often comes up in dating. It also applies to job interviews. I admit that I don't have a lot of dating experience. I do have a great deal of interview experience, especially as the interviewer. They are very similar. What do you bring out and how much do you expose? In both dating and interviewing, it's crucial to make a good impression since you rarely have a second chance. Being yourself does not fully overlap with making a good first impression.
However, this is not an excuse for dishonesty. I strongly discourage dishonesty of any kind. Trying to appear as the person they want you to be often backfires. For one thing, you might be wrong about who you think they are looking for. More seriously, when your true self does come out, and it inevitably will, you will be pegged as the dishonest person that you were. And if you are caught in dishonesty early on, then it's game over.
What sort of things are dishonest in dates and interviews? Exaggerating anything to the point where the other person has heard a lie. Claiming a talent that is at best an interest. Pretending to care about some that you don't, such as laughing at unfunny jokes, or dishonestly claiming to share an interest with your date. The worst form of dishonesty is to pretend to care about the person, or in an interview, faking passion for a company or position. People seem to be unaware that they are caught out as pretenders more often than not.
Back to being yourself, when and how can you be honest in a date or interview? The obvious first thing is to highlight your strengths. That's sort of a given. There is no point in hiding the good stuff. But you have to be careful about how you do this, or it will come off as bragging or exaggeration. And if your strengths don't match what the other person is looking for, it's best to learn that early on. Too many people see acceptance as the goal rather than finding a good match. This is, or at least will look like, dating just to have sex with her, or trying to get a job you're not qualified for because the money is good.
Needless to say, you don't spill your darkest secrets on an interview or an early date. This will not only make you look bad, it will make you look self-obsessed. But you should point out early on something that the other person has the right to know, especially things outside of your control. This includes things like a disability or the fact that your divorce is still pending.
For example, I pointed out on a first date that I had just been laid off the week before. I figured that if things worked out she would find out soon enough. And I wanted to know if this was especially important to her. To my surprise, this became the first thing that attracted her to me: she had a history with dishonest men and she was specifically looking for an honest one. Now, she is my wife.
Another critical but overlooked point is to enable the other person to be themselves. How often do women complain about dates with men who spend the entire evening talking about themselves? I'm sure plenty of men have had to endure this too. Who wants to be with someone like that? Likewise in job interviews, I tend to be suspicious of candidates who ask no questions other than about the benefits. If they are incurious, do they even care? Do they want this job or will any job do?
And so it is with dates. Ask relevant questions. Don't ask about their secrets but do probe a bit into what they are telling you about. Not only will you learn more about them, you may learn if they are being truthful. If you care about who they are, show that in what you ask and how you respond to what they say about themselves. If you don't care, then why are you on the date in the first place?
Feel free to respectfully disagree or contrast your thinking with theirs. Do not put them down, but don't pretend to agree either. Feel free to point out that his jokes are corny. Admit that you know noting about her interests, or have never done her favorite activities. Find ways to make being different a positive thing.
In short, you should be yourself as much as you feel safe to do so, but you should never be someone else.