Dear Carolyn: I'm tearing my hair out over a friend whose life is demonstrably easier than mine in many ways, but who never stops complaining: She doesn't have enough money (her household income is 50 percent larger than mine). She doesn't have enough time (her job comes with six weeks of paid vacation; mine has three). Etc. Etc.

I've tried deflecting and saying things like, "There's never enough time!" Or: "Think of how proud of us our 18-year-old selves would be!" But honestly, it's to the point where I just want to say, "You sound horrifyingly entitled and out of touch, and I don't know whether you're deliberately trying to make me feel bad, but that's the result."

Is there a middle-ground retort?

Carolyn says: Why retort — or deflect — when you can talk?

Maybe your friend is fully in touch with her advantages, and is mindful of how in touch you are with her advantages, and is trying to show you that her life isn't all roses and lollipops just because she has more days off and 50 percent less terror at bill-paying time.

It's a really tough line to walk. Think how your letter would read if your friend, instead of complaining, never stopped expressing how blessed she feels about all the time and money she has.

You see the predicament.

Where there are notable differences in circumstances, there is room for misunderstanding — and room to develop your skills at making connections. That's the argument for diversity in our communities, schools and workplaces: It challenges our comfy assumptions. If you need everyone to be similar to you economically, racially, intellectually, ideologically, sexually, religiously, chronologically, culturally, emotionally — did I miss anything? — for you to feel comfortable, then your life will either be very limited or very uncomfortable.

Now, to be fair, your friend could just be a tone-deaf complainer, also known by the shorter description: obnoxious. (Or is it boring?) If so, then, time to start seeing her less.

But it never hurts to look at your own reactions for signs that your connecting skills have atrophied. In this case, it appears you accepted your reaction — your feelings — as the whole story instead of getting her version from her. You see affluence, assume entitlement.

So work those skills. Challenge your assumptions by seeking her side. You can even do it just by stating yours — for example, when she complains there's too little time: "You do have six weeks off a year, though — I envy you that." Not meanly, and not every time, just honestly.

Go for it

Dear Carolyn: A close male friend introduced me to a woman he wasn't involved with at the time. We were attracted to each other, she gave me her phone number with him right there. Before I contacted her, the two of them did get involved, but not exclusively.

Now, he has a different girlfriend. Does this leave me free to pursue the woman he introduced me to? It just feels a little bit funny to me.

Carolyn says: People decide whom they date. Their friends and exes do not. Good luck.

E-mail Carolyn Hax at tellme@washpost.com, or chat with her at 11 a.m. Friday at washingtonpost.com.