Oh man, your life is MESSED UP right now.

Not that anyone asked us. But they can officially start.

Send Jilly your questions by filling out the form at the bottom of this post or right here, and she’ll send you a piece of her mind.

Because during those troubled times, it’s always important to ask yourself: What WOULD Jilly do?


Over the summer, my husband and I always take a weekend to visit one of our friends from college and his wife. I always end up getting paired off with his wife, who he met after college, I guess because we’re the girls. The problem is she’s desperately boring. Not only does she talk about the most inane stuff (all the details of the meal she ate a week ago, or the step-by-step plot of some TV show I told her I don’t watch, or the personal history—including birthplace, height, weight, and past achievements—of the girls currently on the cheerleading squad at the college she graduated from), she never stops talking! Silence, even awkward silence, would be better than having to pretend I’m interested in all the pointless stuff she talks about … endlessly. Is there a polite way to just tell her to shut up already?

-Wishing For A Deaf Ear

The short story:

there isn’t a polite way to let her know that you care about her conversation slightly less than you care about a detailed recitation of historical prices of paper clips over the last 100 years.

That doesn’t mean you have to just sit there and take it, nodding and smiling and slowly losing your will to live.

But it does mean you may have to white lie a little.

The next time she starts in on a detailed discussion of why she switched from regular shampoo to “fine hair” shampoo, stop her with a kind word (and a slight wince): “I’m sorry, I really want to talk about this with you, but I have a little headache right now and I’m finding it hard to focus. Do you mind if we talk later instead?”

Other possible deflector lies include:

1. That drive in really wore me out—would you mind if I lie down for a while?

2. That totally reminds me of this episode of (YOUR favorite show). Do you have on-demand? You have to watch this now, but we shouldn’t talk; there’s a lot going on and it’s easy to miss something.

3. Not to be a total bore, but I have a few e-mails I really have to get to before I go into full-on vacation mode. I’m just going to go finish those up.

Unfortunately, you may have noticed that all of those lies buy you time … but not a whole, chat-free weekend.

You have a couple options: force her into activities (when you have a chance to get a few words in edgewise, mention a desire to shop, or play croquet, or go on a loud jetski ride). Make sure you like the activity enough that it’s not just compounding your boredom, of course, then dive into it as quickly as possible. Added bonus: if you happen to just completely tune her out and she calls you on it, you have a built-in apology: “I’m sorry, I just got distracted by this peplum. Let’s try stuff on!”

Another option is to bring (drag?) the husbands into your gab-fest. After all, you might not be getting paired off by gender; you might be getting foisted off on a known bore.

Of course you can also just be (somewhat) straightforward: ask her directly, when she starts off on another pointless tangent, if you could just have some quiet time.

But don’t be surprised if she either is offended, or starts up again quickly (and another request will almost certainly offend).

And then, of course, be even less surprised when she tells your friend (the husband) about how rude you were to her, in minute detail.

I have a work friend who consistently overshares. It seems like she has no filter whatsoever; we could be discussing our weekends and she’ll cut in to note that hers would have been better if she hadn’t had a yeast infection (not even exaggerating). I really like her, but I don’t need to know THAT much about her. But at the same time, I’m concerned that if I say something, our working relationship—not to mention our friendship—could become seriously awkward. What should I do?

-I Know Too Much

The difference between your situation and that of the first letter writer is pretty simple:

You want to embarrass this friend.

Not maliciously, or unnecessarily, of course. But her root problem seems to be that she doesn’t have any sense of when she’s saying something totally inappropriate.

Next time she tells you about a particularly hardy fungus she’s recovering from, pull her aside from the group (once you can do so unobtrusively), and tell her exactly what you’ve said to me:

“I have to tell you, that is a LOT more than any of us needed to know.”

Hopefully a couple call-outs will give her a better sense of which stories she should share, and which are just oversharing. If learning that difference is enough to make her incapable of treating you normally, then she doesn’t seem like the kind of friend you’d want to keep around…especially around children or clients.

You’ve Got Problems (But Jilly’s Got Answers)

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