Be blunt with friend who can't read social cues

Q. I need some help setting boundaries with a friend who has a hard time reading social cues. She regularly interrupts and talks over me, dominates conversation with stories about people I've never met, continues texting after I say I'm going to bed, and overstays her welcome when she visits. For example, I say I need to pick my kid up between 3 and 4, and at 4 she's still sitting in my living room while I practically pack her bag for her.

I don't think any of it is malicious - I think she's just socially inept and at the same time a bit desperate for connection. The main thing I value about the friendship is that I can be honest with her about many of the things I'm struggling with because she's going through similar difficulties.

And yet, when she interrupts me or overstays her welcome, I find it incredibly difficult to just say, "Please let me finish," or, "I have to go now." The idea of addressing any of these problems directly, i.e., "When you [blank], I feel [blank]," fills me with utter dread. I'm just not sure why I'm having such a hard time with this. I'm annoyed and I know it's my own fault.

A. Yes, it's your fault, but that's good in this case. First, it's not a mistake of malice or negligence or anger; it's a mistake of sympathy. You think as someone who does read social cues, so you act accordingly. Good side to err on in general, if not specifically here.

Plus, being at fault means you can fix it, maybe unilaterally:

Instead of cuing her as you would others, as if she'd get it, embrace the chance to be blunt. Interrupt her to say [hands up in a "stop" gesture"], "Hold that thought, apologies for interrupting."

Then: "I'll be late if I don't leave right now. Here, walk me out" - then get your keys and hold the door for her. "We'll pick up your story later?"

And/or: "Let's talk about people I know."

And/or: Turn off your phone.

It's difficult at first, because you have - most have - been socialized hard to push and pull gently with peers, till you achieve equilibrium. People who don't read social cues well can't feel that kind of subtlety well enough to match it, and so will annoy or overwhelm people trained to smile and endure. The "When you/I feel" construct is not her native language. Adopting clear statements in the moment is the way to achieve balance - and, with practice, liberation, not just among the subtlety-challenged. Almost everyone misses a cue here and there.

To get past initial discomfort, know that it's an act of kindness. People who can't find a way to navigate long-talkers tend just to avoid them. Thus their loneliness (which exacerbates the talking). You needn't look any further than your own alternatives to see this: You either quietly endure this friend and her "difficult" company, or shed her. Ouch.

The middle way of clear communication - which might even feel rude in a different context - is, counterintuitively, the compassionate one. It's a chance for you to share a friendship based on real and honest connection - the very thing that likely eludes her.

If you get wounded responses? Cheerfully: "We're fine - I just need [blank]," which you then prove by inviting her back.

Q. My sister sent my grade-school child a check as a gift. We deposited it four weeks later, and it bounced because the account was closed.

It's a small sum, $25, and the charge against my child's account was another $10. This is not about the money or any issues I have with my sister. She made a mistake, no big deal. I'm curious what the general rule is. I would want to know so I could correct it, but is there an etiquette standard?

My sister is going through a divorce. We have a good relationship. Her financial situation is rather unknown to me, but not as solid as mine. Do I contact her or just cover it out of my pocket?

A. "Going through a divorce"="going through hell," of one form or another. So eat the money as your quiet gift to her.

If she weren't preoccupied or struggling, then I'd still advise you to eat it. There's just not enough to be gained with such a small sum in such a small-gift context to make it worthwhile to say, "Your check bounced, please write another so I can have my money."

It's easy to say you'd want to know if you were in your sister's position - I'd say the same, of course - but the risk of that little bit of virtue getting swamped by ick is just disproportionately high. And the risk you'll wind up asking yourself why you thought it was a good idea to ask for the money verges on 100 percent.

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