Oh dear, that's a tricky one. I sympathize with both parties. Judy's head must be spinning so fast with terror and a sense of helplessness and that she's unable to think of anything else—and likely looks forward to these dinners as a chance to vent. At the same time, I can see how the other women in the group, while initially sympathetic, now feel burdened and even offended by Judy's total domination of the conversation at the expense of their own chances to gossip, gab, and expound on the mysteries of the universe.
I wouldn't tell Judy about the other women choosing to dine without her. I also grant you permission to attend the alternate group's dinners without feeling guilty. (It's not as if you organized these events; your only "crime" is having been invited to them.) But I'd also take Judy out to dinner on her own and carefully suggest to her that, while you and your former colleagues are happy to listen to her talk about her sister, it sounds to you as if she'd really benefit from talking to a professional who could help her deal with her grief. If Judy fails to take your advice and continues to perorate about the curative properties of sheep sorrel or Indian rhubarb, feel free to limit future meals together—and to keep a newspaper or iPad under your seat—but don't cut the woman off. You may well be Judy's one lifeline right now. Please note, however, that if her sister has indeed been diagnosed with a fatal form of cancer, the status quo is unlikely to last for long.
Friend or Foe
Dear Friend or Foe,
I met "Jessica" in college, and she has always been competitive. But she was also supportive and a great listener. In the past few years, however, her competitive side has become suffocating. She belittles my accomplishments—at one point, she said that enrolling at the Ivy League (graduate) school to which I'd just been accepted would, for her, be a "backup"—and regularly omits unflattering details about her own life. She got fired and later called it her choice. At the moment, we're both in graduate programs, mine underfunded, hers at a wealthy school. Jessica is constantly telling me how pleased she is with her financial situation. If I say that I studied for eight hours, she studied for 10; if I was mention that my adviser is great, hers is a genius who thinks Jessica is the best student in her program.
I'd love to talk my feelings over with Jessica, but every time a friend tries to confront her with an issue she simply ends the friendship. So I'm reluctant. She's also incapable of apologizing. Our conversations now consist of her updating me on her résumé and me avoiding any discussion of myself and trying to end the call before she upsets me with a casually callous comment. I'm getting married next year and would love advice on how to handle her judgmental attitude and one-upmanship. (Jessica is, of course, a bridesmaid.) Is there any way to address the situation, or should I do what my fiancé says and drop my relationship with someone he believes to be an incurable narcissist?
Missing My Old Friend
I'm with your future husband. You say that Jessica was a great listener—once. But it appears that it's been years since she listened to you with any purpose other than to diminish what you've just said. You also say that Jessica is competitive, but it sounds to me that, above all, she's madly jealous. Your upcoming nuptials will likely only make the situation worse. Don't be surprised if, the night of your wedding, Jessica somehow manages to make the drama all about herself. On that note, and unless you have an appetite for masochism, I'd cut bait now. If you already sent the invite, it's too late to disinvite her. But you can always be a bitch and backtrack on the bridesmaid offer. Say you've decided to limit the number of maids to two or four (or whatever number you'd planned, minus her). If Jessica says "how dare you," tell her you feel as if the two of you have been drifting apart for years now and talking at, not to, each other. If she turns on you and ends the friendship, she'll be doing you a favor.
Here's some big picture perspective: Later in life, most of us wind up with only a tiny handful of pals from college. (I'm talking two or three.) Whatever happens around the wedding, I'd say the chances of you and Jessica being buddy-buddy at age 40 is basically nil. Good luck and happy wedding.
Friend or Foe