How do you "pick your time"?

One way is, “I’d like to talk to you about something serious. When would be a good time for you?” That gives the other person some agency and time to prepare for an intense conversation.

It could also be worth discussing or getting some ideas yourself for a safe or potentially peaceful setting. In some instances a coffee shop or walk could be best or a car ride, but in others, maybe a room in the house would be best. If you think the conversation might get explosive, you’d probably want to give yourself an escape plan by leaving a metaphorical or even actual door open.

And if the time is past but the talk still needs to happen, no using regretting but just do your best planning it now.

A book came out a few years ago called Difficult Conversations that I thought was very useful. You might want to look for it.

Some people believe that doing it in public is the best way. My mom did this to me. I don’t agree. Perhaps after a nice dinner at home, then say, I have something to discuss with you, and dive in. Some things will never have a right time, but avoid “worse times”, say after their dog gets hit by a car.

Oh, yikes, this kind of thing is so hard. I think context is important. I am in favor, in some cases, of prior warning of serious convo to come, so as not to blindside. In my family of origin, however, warning of a difficult thing usually meant that they would attack me to forestall anything unpleasant that I might say. With a person who might have anger issues, the coffee shop is the way I would go, and I’d have my own transport ready.

I do very poorly with confrontation, and I do best when I write a letter. I can carefully choose my wording, and I can’t be interrupted. I have been told that that is cowardly, but I don’t care, it seems to work for me. I do poorly in the “heat of the moment” scenarios.

@kneesox I just read your tags and see that you may be expecting violence or arguing over your conversation. Can you have a friend or relative with you to help calm the situation if needed?

I don’t do well with confrontation, so I tend to be passive unless someone confronts me first.

What helps me is to not think too hard about a good time, but as long as we’re alone, to just start talking. Once the topic is coming out of my mouth, there can be no turning back. I may be saying to myself “I don’t believe I’m actually saying this” but it will be coming out.

This reminds me of something I’ve been fretting over. My daughter’s twin friends’ mom asked me to take their two guinea pigs in the fall, 7 months ago, when they were having work done in their house and also simultaneously the mother had a personal crisis going on. So I took the guinea pigs, cages, etc. and then she never asked for them back (with the work completed in the house but the personal crisis still ongoing) and I didn’t push it. Around December, one guinea pig died and in February, the other one died. I never told her, and I don’t know if the girls would be upset at this point or not care, but I keep putting it off. Next weekend (in a week and a half), I’ll be hosting a small party for my daughter’s birthday, and I want to tell her prior to that,. I don’t want the girls to come into the house expecting to see the guinea pigs. So I’m in the same spot you’re in right now.

There’s no good time, usually that just delays the inevitable. I’m more of a ‘tear the band-aid off’ type. Ask to meet and be calm, then just say it.
I prefer that with receiving bad news as well, tell me and let’s deal with it.
Best of luck.