Q: Iím tearing my hair out over a friend whose life is demonstrably easier than mine in many ways, but who never stops complaining: She doesnít have enough money (her household income is 50 percent larger than mine). She doesnít have enough time (her job comes with six weeks of paid vacation; mine has three). Etc. Etc.Iíve tried deflecting and saying things like, "Thereís never enough time!" But honestly, itís to the point where I just want to say, "You sound horrifyingly entitled and out of touch, and I donít know whether youíre deliberately trying to make me feel bad, but thatís the result."Is there a middle-ground retort?FriendA: Why retort ó or deflect ó 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 isnít all roses and lollipops just because she has more days off and 50 percent less terror at bill-paying time.Itís a really tough line to walk. And if you donít believe that, then please give a momentís thought to 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.Where there are notable differences in circumstances, there is room for misunderstanding ó and room to develop your skills at making connections. Thatís 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, intellectually, ideologically, chronologically, culturally and emotionally 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 thereís too little time: "You do have six weeks off a year, though ó I envy you that." Not meanly, and not every time, just honestly. Let your perspective be her invitation to open her mind ó and possibly even to change it.