What approach do you prefer in such situations (details inside)?

@imrainmaker If it is something that would upset them I might weigh whether or not they need to know. And hypothetically, I might tell them sooner than later. Good luck.

Been there, done that. It was news that harmed no one, but would upset them because of differences in social and moral ideals. I told them sooner, so they could get used to the idea before the actual event happened.

I hope you can resolve this satisfactorily. Good luck.

Without specifics, I don’t know, but if you’re going to tell them eventually, it’s often best to tell them sooner rather than later. People who are close to you generally want to know. Ask yourself if the situation were reversed, would you want them to tell you or keep it from you (or keep it from you for a while and then tell you)? Mostly I have heard from people that they want to know stuff rather than have things hidden from them. Mostly when I’ve told myself I ought to hide something from people, I’m doing it because I’m afraid and wishing not to confront it, but it just hangs like a heavy cloud for me until I tell people, and after I do I usually feel a bit foolish for having withheld it.

I would delay until I was ready and knew what I was going to say. But I would not wait until the last moment.

In general, I’ll be nice and super sweet when attempting to bring the subject and perhaps say something like “please/promise don’t be mad, ok?” A good partner is a forgiving partner for understandable mistakes that will upset them. Don’t forget to be extra grateful and cheerful when they forgive you. Say something like “you’re the best/most understanding” and follow up with a nice back rub (so that they will likely to forgive you again next time lol).

Other than that, decide the best time to bring the subject and judge your loved ones condition. Don’t ask when they’re already upset for other reasons or having too much problem on their plate at the moment. Make them happy, relax, and fill their stomach and then you could ask the possibly upsetting question.

Thank you all for your great answers!!

Up front. I think open honest communication is the best for everyone.