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Multiple times I've been struggling with the following issue:

Say colleague A chat with me about some kind of 'secret' (lets call it, X) about colleague B, and after he/she told me ask me: 'Please, don't tell anyone'. After some time, when I'm talking with B somehow B asks me if I know about X because he/she is suspicious everyone knows it, or maybe it tells his 'secret' X with me and I should pretend not knowing.

The problem is: If I tell B that I know X, I'd have a problem with A. If I don't admit I know X with B, I'd be lying to B.

That kind of situations makes me quite uncomfortable... what would be the right way to handle this kind of situations?

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    I think this is almost impossible to answer generically - the right thing to do will depend entirely upon your relationship with the parties and the type of information. Generally, though, keeping quiet is the best policy - it's partially dishonest, but most people appreciate that sometimes you are simply not at liberty to reveal information. – Dan Jan 25 '14 at 18:23
  • Depending on your role in the company, you may be asked to maintain confidences which is part of the job as if you are in management you may be told about stuff coming soon that isn't meant for everyone to know. – JB King Jan 25 '14 at 22:01
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The best way to handle this is to refuse to keep secrets or enter into gossip. If that's impossible, then at least refuse to accidentally promise to keep secrets.

Hey, Matthew, did you hear about B? I mean, don't tell anyone I told you, but --

"Sorry A, I don't want to hear something I can't tell anyone."

Or, at the end of a long conversation in which you learned a LOT (whether you wanted to or not)

Man, good stuff eh? But listen, don't tell anyone ok, because if this got out B might get fired or even divorced.

"Sorry A, if you wanted this off the record you should have said so. I'm not going to blab it around to everyone, but if I get asked, I'm not lying about it."

The more you use these two sentences the more others will think twice before putting you in this position.

As for reacting when B tells you something you already know, a simple "Really?" or "Oh my" or "I'm sorry to hear that" is all that's needed before you discuss it exactly as you would whether you knew already or not. "What are you going to do?" or "Is it serious?" or "Is there anything I can do to help?" for example.

If someone asks you "did you already know that X?" I can't see lying being a better approach than the truth. You could try "I heard some rumours that could be interpreted like that, but I didn't know for sure one way or the other." That's as close to lying as I would be willing to get. You don't have to answer, of course: you can reply "Why? Is that's what's been going on?" or "What? Are you saying X?" and then go on as in the case where they tell you something you already knew.

My answer to a gossiping question may also be relevant here.

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