Do I warn about affair emails? Even though I deleted the messages (some of which were quite explicit), I fear they still exist somewhere Some years ago I embarked on an affair with a client and used my work email to communicate with her (I know, I know). The affair has long since been over, and I don't think anyone ever knew about it. But now our company is under investigation for something quite different and investigators are crawling all over emails from that period. Even though I deleted the messages (some of which were quite explicit), I fear they still exist somewhere. Should I warn my superiors, with whom I have an excellent relationship? Or should I keep my head down and fingers crossed? Executive, 48 Lucy's answer Yes, you fear right. Emails, like herpes, last forever. The embarrassing messages you sent to your erstwhile lover are still sitting around somewhere - but so too are all your colleagues" ill-judged emails. That means there will be a mountain of messages for the unfortunate investigators to get through. They cannot possibly read all of them, and even if they do read yours, they are most unlikely to report you as what they are looking for is not a long-ago affair, but something quite different. Suppose they did show your emails to your superiors, what then? I can see why your wife - if you have one - might mind. But I do not see why these bosses would be terribly upset - unless your affair with this woman hurt the company in some other way. If, say, she was one of your most important clients and you got tired of her, dumped her and she took her business elsewhere, that might not look good. Neither would it look good if you were buying her gifts and letting the company pay for them. Remember Mark Hurd at Hewlett-Packard, who quit as chief executive after a relationship with a contractor was exposed? What did for him was not the relationship itself but code of conduct violations that were unearthed in the internal investigation. If you were too free with your company's credit card, it is possible that you too might get caught out, though I doubt it. One difference with Mr Hurd was that he was already under investigation. You are not. So I think it is probably going to be fine. And even if it isn't fine, there is nothing to be gained from alerting your bosses. The time to have confessed would have been back then. To do so now would be mad, as it would make it clear that you were not coming clean out of any desire for openness, but simply out of fear of exposure. Head down and fingers crossed is the only option. Comfort yourself with the idea that you will not be alone. At the time you were writing those cringe-makingly explicit messages, there were an awful lot of other fools equally oblivious to the idea email is not private.