to give him the reference. Yes, it was wrong of him to put you down without asking, but I think he deserves the reference.

Why? Because he’s young. It’s really, really tough to be young in the professional world, with absolutely no experience to prove to yourself or potential employers your worth. You claim nepotism got him his job at your work. Maybe so. But look at your own description of him:

insecure, mumbling and inability to make eye contact were standard whether he was under any particular stress or not. He was paralyzed by indecision and lack of self-confidence and had to be hand-held through the simplest tasks.

And as you yourself emphasize

He had zero initiative because of these confidence and communication issues.

He’s clearly not the spoiled son expecting to coast by. He’s insecure, inexperienced, and seems to be trying. It's often harder for the child of a successful parent to believe in himself, harder to establish self-worth. Look at the children of famous people. I'm not saying that's a lifelong excuse. But I'm saying we can cut kids some slack.

I can’t believe your reputation hinges on his. You have your own career, your own work history to rely upon. And it's a single reference on a single occasion. As time goes on, his employment history will speak for his abilities or lack thereof.

Cary's suggestion of an e-mail offering guidence but kindly making the point that you must asked beforehand in the future is spot on...though I think telling Dad is pretty useless and more likely with increase rather than alleviate the drama.

Just remember we all start out young and scared. Being the boss’ son doesn’t magically obliterate that. In some instances, it might exacerbate the problem.

It's so easy to take a callous, cut-throat-business approach. I'm glad you didn't.

I can’t believe the letters going on and on about “protecting yourself” or “set policy” or “don’t worry, the subtext of your comments will effectively trash him.” I know there are a some kind people offering advice here, too, but I’m shocked just how coldhearted so many responses are.

Can we remember it’s a young kid involved? An inexperienced kid? What’s so hard about saying a few nice words? Words that don't carry a negative subtext?

Looks like the business world is pretty effective at sucking the souls out of people.

And Anonymous, I agree.

There is nothing, absolutely nothing, wrong with being judgemental about your sister's affair. We have to get past the point in this country where we're terrified of taking a moral stand. I think maybe the example of our leaders, who bomb people they judge, makes us think that all judgements, all moral certainties we may reach, are dangerous. That's wrong. We have to make a determination about what is right and what is wrong, and we have to act on it.

However, that does not mean you need to rat out your sister. Others insist you need to tell the wife, something you weren't suggesting. I'm not sure if you know the man she's dating, so maybe it's a moot point. I understand the concerns other letter writers have about the spread of herpes and the danger to an child born to a mother during a breakout. I understand how tempting the idea of telling her secret to someone "for the good" might be. But, first, the child was already born with apparently no complications. There is no guarantee the wife contracted herpes or even that the husband did. If your sister do not have sex with him during outbreaks, it's pretty unlikely, if not technically impossible, that he did; and since your sister was the victim of a vengeful man who intentionally gave her the disease, my guess is playing the same role is the last thing she'd do.

But that's a side point, and the core issue is that, essentially, you're in the role of the priest. You heard something because your sister needed to unburden herself, and she unburdoned herself because she knew the information would safely be left in the "confessional." Beyond doing her that service, nothing is required of you except that you honor her trust—and, essentially, honor your bargain. Because there clearly has been a bargain between you that what she tells you will remain confidential.

Now, if you want to change the bargain, you can choose to do that. And there's no reason why you shouldn't, considering the pain it is causing you. You can say to her, "I can't listen to this anymore. If I keep hearing about this, I'm not going to be able to keep this to myself. Find someone else to talk about this with. Because if you keep talking to me, you'd better expect to have some heated conversations with our sister and our mom in the near future." That respects your previous relationship and lets you off the hook in the future. You might also want to suggest that since she clearly needs to hash these things out with someone, maybe she should discuss her issues with a therapist. That would be someone who could listen in total confidence and also help her develop the tools to improve her life.

But as far as what's she's told you so far, I think you need to remain silent, no matter how good an excuse you happen upon that would allow you to feel you have permission to talk.