I’,\m sitting here wondering what makes this so complicated.
First I ask myself why is this even an issue. Why can’t we sleep with whoever we want? Is it infidelity if it happens befoe marriage? Why does sex with other people threaten us so much?
My second question is why should anyone be afraid of sharing the information? I think we might be afraid of anger and repercussions. We might not be believed, and even if we are, the messenger is often shot. In any case, both members of the couple may come after us in some way. Is that risk worth the potential benefit?
What is the benefit, anyway? Is there any obligation to inform a stranger? I think there is an obligation if you believe they will be hurt without the information.
And what about my reputation? Will it suffer if people find out I’m sleeping around and having one night stands with random strangers? It could happen.
Whose moral responsibility is it? I think the guy should tell her. But maybe their relationship does not require honesty.
If you decide to tell, how should you do it? An anonymous letter is the worst way to do it. If you tell, you have to stand behind your accusation. She needs evidence, not just a poison pen letter. She won’t know what to believe, and will think someone is just jealous and trying to poison her relationship. If you can’t do this straight-forwardly, don’t do it.
If you believe you are truly helping someone, and she is somehow unaware of the character of her fiance, then tell, and tell to her face. You have to be able to look her in the eye on this, or you won’t be believed.
If you can’t do that, don’t tell. You aren’t helping.
If I were to tell, I’d do some research first. I’d try to find a friend of hers I could talk to, to see how much is already known. Then I’d work out an approach. But you are in a precarious position. You’re the one who slept with some guy without knowing him. You’re a loose woman, and as such, your honesty is quite questionable. This is not a judgement. I just think this is what people will think.
Anyway, I can’t offer an opinion. There’s not enough information. Every case is individual. No one size fits all in situations like this. It’s truly hard to know what the right thing is. I wish you luck, and I’m glad I’m not in your position.