Friend or Foe: Should I Stop Bankrolling My Buddy’s Bad Choices?

Welcome to "Friend or Foe," a regular DoubleX advice column for your queries about the trickiest of all love affairs: friendships. Lucinda Rosenfeld, author of I'm So Happy For You, a novel about best friends, is now taking questions at lucinda@imsohappyforyou.com.

Dear Friend or Foe,

For most of my life, I’ve known a woman—“Prissy”—who has to have things her way, requires the undivided devotion and attention of men, and compartmentalizes her life to the point where, if it’s not convenient, I’m not part of her existence.

Since I have an expansive career, friends, and family network, this really hasn’t bothered me much over the past nearly four decades. In recent years, I’ve watched her three marriages and countless other relationships fail. She has developed (or feigned) a debilitating illness, yet she keeps a large garden and house immaculate and cleaned out her aging parents with cash to spare, despite being on the government dole for aforementioned illness. The final blow: When Prissy mentioned she had an overabundance of an indulgent fashion item of her mother's (whom I knew well in my youth), I said it would be nice to have one.

"Oh no!" Prissy replied, almost indignantly, "I plan to sell them all on eBay."

At that precise moment, the years and tears and crushed feelings resurfaced.

Since then, I’ve declined her telephone calls (she hasn't visited me for decades, despite living just a few miles apart). I’m neither wealthy nor fashionable—and I know things don’t make one happy—but I’ve worked very hard for all I’ve accomplished. And I would have appreciated a memento of her mom's vibrant youth.

My query: How do I deal with this persisting personality, who all her life has been pampered and prosperous, and with whom I no longer wish to be associated?

Sincerely,
Can’t Take the Lies and Snubs Anymore

Dear CTTLASA,

Wait, you’re telling me that you wept after Prissy failed to hand-deliver one of her mother’s frayed Chanel handbags? I guess I’m a little confused, since a) we’re ultimately talking about a piece of leather (or a fur coat or a diamond necklace) here; b) you say you don’t particularly care about “things,” and c) it belonged to her mother, not yours.

As for Prissy “cleaning out her parents,” since you’re not a member of the family, how can you be sure that her aging ‘rents didn’t bequeath all their cash and possessions to her in anticipation of their deaths? Nor do I see how Prissy’s three failed marriages constitute a blow to you. It seems to me that these are her own failures—and she should not be resented for them.

As for her “feigned illness,” if that’s really what it is, I agree it’s annoying to think of her receiving taxpayer handouts. (I have a friend who manages to elude Uncle Sam and it never ceases to irk me.) But, again, her failure to play by the rules is not really a personal affront.

Since you say you have such a full life, I suggest you get on with it—and leave Prissy’s to Prissy. If you really want a designer bag (or whatever it is), start a “mad money” account at your bank and deposit 50 bucks in it every month. At the end of two years, you’ll have bought your own. Even better, find out when Prissy is putting the goods up for auction, and get in there with an early, solid bid. Chances are you’ll get your memento, after all.

Sincerely,
Friend or Foe

Dear Friend or Foe,

I've been friends with "Sally" for eight years. When we were in college, Sally and I were really good friends, supportive and encouraging of each other. But ever since we graduated three months ago, she's suddenly become a mean girl.