The Art of Subtlety.

So there’s these two relatives. He’s on his 40s, she’s on her 70s.

Years after a difficult separation, they arrange a meeting in a public place of choice. She’s traveling with her friends.

He wants a few quality moments with her and does not want the friends around.

How can he persuade her to separate from them while they meet? A casual excuse of some kind? Bending the truth or even lying would be ok as long as there’s no hurt feelings.

Um…how about saying, “I’d like to talk to you for a few moments alone?” Why the need for orchestration?

Is she going to want those quality minutes alone? If you’re not sure that she will, you need to ask. Lying to get her alone is profoundly uncool.

Well, because by all odds it will be a difficult encounter where there is not much to be said other than what might spring out of it. Actually the less direct conversation, the better. Picture a post-divorce like situation.

Also because the meeting, if it goes well, might last hours, not just a few moments.

She’s the one who’s pushing for the meeting. But she might feel supported by her friends, that’s true.

That the request can be made is a given. The problem is how to do it. Acting cool, sounding casual, with no drama.

Hours? He needs to make a date with her, with that explicitly specified.

“Look, I need to talk to you, and it’s gonna get serious, and I’d like to do this with just you and me, no one else. Is Wednesday good?”

She might very well tell him to go to blazes. Or to put it in writing. And she might want a witness, and refuse to meet alone.

Or…she might agree. Who knows?

But he has to ask, and he has to put it all right up front. No trickery, no orchestration, no bait-and-switch. “I need to talk to you, alone. It might take some time.”

He could offer to buy dinner. That provides at least that much incentive, and also puts the venue into a public place, so she knows she’s physically safe.

“Okay, I have to listen to him for an hour as he unburdens his soul. But I get dinner. Fair enough.”

“she’s physically safe”

Oh dear.

What kind of place is this?

They are relatives which had a difficult break-up.

Man, if there’s another reply of this sort I think I’ll maybe try a chinese forum or something related where the first assumption is not that you are a weirdo.

Well, since “break-up” implies a dating or sexual relationship, and these people are thirty years apart in age and related, who’s the weirdo?!

This sounds like some middle school kid stuff to me. If he is a mature 40 year old why can’t he just tell her that he would like some time with her alone and let her choose where?

Or he could punch her in her arm so she can chase him away from her friends…

Oh God. Can the moderators please delete this train-wreck of a thread?

Y’call this a train-wreck? Kid, I’ve seen train wrecks compared to which this is The Muppet’s Christmas Special.

Anyway, the serious answer is that honesty is what’s called for here, not subtlety.

And don’t ask for advice if you’re not willing to listen.

Roamer, your request is very unusual. I don’t think I’ve ever had anyone use trickery or lies or subterfuge or subtlety or anything like that to try to get me alone to meet with me, with the possible exception of a woman or two who wanted to jump my bones. In those cases it was okay, because hey, bone-jumping.

But the dude who’s looking to trick an older relative into being alone with him after an extremely fraught relationship? That just sounds like a terrible idea for a lot of reasons, starting with the fact that it doesn’t sound ethical at all.

If the alone time is really necessary, how about an email? “Hey gramma–when your friends visit, is there any chance just you and I can go grab a cup of coffee at some point?”

How about ‘hey, can we go somewhere and talk for a few minutes?’. She’ll either say ‘ok/sure I’d like that’ or ‘no thanks’. If she says no, then you need to move on.

Meet somewhere like a museum, so the friends won’t just have to stand around waiting for her with nothing to do. Greet and make small talk with the group for a few minutes, then say directly to the friends “I hope you don’t mind if I steal Margaret away for a bit so we can talk.” Turn to her, and say “can we have a quick drink in the cafe?” Assuming she does not object, you’re in.

My first wife died in a train-wreck. How about some consideration? Maybe a trigger warning?

If you gave more details you would get better answers here. What caused the rift? What are the two parties hoping to accomplish by having a meeting?

I’ve had good results with ether.

Set off several smoke bombs down the hall as a distraction. In the panic toss a sack over the old lady and drag her out the back door into a waiting van. Drive around for at least half an hour taking lots of extra turns so she can’t keep track of where your going. Head for an abandoned warehouse out in the industrial district. I assume you have your ransom note already prepared. Don’t do that old thing with cutting words and letters out of magazines, too much chance of picking up a fingerprint, just wear gloves to load fresh paper in the printer. Make sure to use a large bold font, and definitely not comic sans. Money drop offs aren’t what they used to be either, bitcoin is the big thing in ransoms these days. Good luck in federal prison!

Scheming to get her alone makes it sound like you expect there will be some resistance on her part to the idea and perhaps there is a reason she agreed to meet in the presence of her friends. What do you expect will be accomplished by separating her from her friends that can’t be done with them present?

Thank you AnaMen. Thank you! Thank You!
You got the gist of the matter.

The museum is a great idea. They can be together but not explicitly focus on each other, the tour can potentially last however long is desired and the subject of the conversation can easily be changed if it starts to veer into perilous directions. “Oh, look at that. How curious it is, is it not? Did you know that? I didn’t know that.”

The small talk first is also a great idea although he’s terrible at it.
The key phrase to the friends is good too. Can you think of any more of similar vein?