Whiny friend seems ungrateful for the good things in her life

Q. I have a friend who, by most any measure, has a lot to be thankful for. She has two lovely children and a husband. She's able to work only part time (though she hasn't gone back since child No. 2). They own their home outright and just bought a second in a beach neighborhood where they'll move once they remodel it. They travel to see family in far-flung places.

Mostly, though, when we talk, she's complaining about something. Not everything, just something. Whatever happens to be consuming her at the moment. Admittedly, these things are sometimes big (difficulty getting pregnant), but there is ALWAYS some sort of struggle consuming her, possibly for months at a time. And I rarely if ever hear gratitude.

This strikes me as ... off. She's made conscious, very-thought-out decisions about family, home and other aspects of her life, so it's not like she just ended up here and doesn't know how. Can I say to her, "Are you grateful for fill in blank? I've been wondering because I don't really hear you mention it."

Or is that really judgy? I honestly want to know, because I find I'm liking her less without knowing. She seems to take her life for granted, or expect that she is guaranteed some things in her life, and this really bugs. But if it's just a matter of not verbalizing gratitude, OK, I can get that. I think.

Judgy?

A. Or she's genuinely unhappy. It can, of course, happen amid gaudy equity, lovely kids, an attentive spouse, a flexible career, stable finances and ambitious travel; just because these have societal value doesn't mean they're valuable to her.

And just because the decisions were "very-thought-out" doesn't mean they were the right ones for her. If a person's baseline understanding of herself is a degree or two off, then her choices can lead her, over the years, hundreds of miles off course.

What if she doesn't get along with her husband, or feels unsuited to at-home parenthood, or answered her ambitions while neglecting her soul? These deep investments she has made can easily sag into burdens.

On top of this, as I continue to argue for sympathy toward an affluent whiner, there's the additional weight a person can feel when making (supposedly) all the right choices results in misery. Who will weep with her in her freshly remodeled beach house? Who will help her understand why she feels like nothing while having everything? Whom can she blame but herself?

Granted, this is but one possibility, and the ones you touched on yourself are just as possible. Could be, too, that she's bored or adrift, having arrived too early at her life's destination. Or her good fortune has metastasized into entitlement. Old stories all.

But since she's your friend, try saying something that doesn't prejudge and instead reflects only the facts you have in hand. "You appear so fortunate from the outside," you can say, "but when we talk you're often down about something. Give examples here of anything trivial. i.e., not her fertility struggles." Then you ask, "Are you OK?"

Do hold up a mirror for her, yes, but in a loving way. That makes it about her well-being, whereas judging would be about you.

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