Dear June,

Last year my husband died after a long illness. About a week before Carl died my closest friend, “Hepzibah” (ugliest pseudonym I could think of), who has known both of us for over twenty years, decided that she had to tell me how she and my husband had had a “torrid but short-lived” affair about seven years earlier. “Short-lived,” it turns out, means five months, and probably the second-worst five months of my life, when I was having painful cancer treatments and had no idea how things would turn out. I told Hepzibah, among other things, that she’d picked a hell of a time to tell me. She replied that it was just like me to pounce on irrelevancies. She never actually expressed any remorse or even regret over the affair during this conversation, just said that she thought it was important to clear the air – not the greatest way to put it while my husband was slowly drowning from COPD and gasping for breath. Anyway, I was not about to mention the issue to him since he was, you know, dying.

Hepzibah and her family came to the funeral, but she and I have not sought each other out since then.

Soon after Carl died, another very close friend moved to Japan, and my only sister started showing signs of early-onset dementia. It began to dawn on me that I had always thought I had lots of good friends, but that without my core of Carl, Hebzibah, my sister, and my friend who moved to Japan all I really had was a network of neighbors, acquaintances, fake work friends, and couples who see me only as half of me-and-Carl. (I do have two fine kids, but that is not the same, and they are both far away, in college and med school.) I have plenty of company when I want it, but I am still terribly lonely. I am thinking of making an overture to Hebzibah. What do you advise?

—Desolate in Des Moines

Dear Dee,

I definitely advise you to try to make some new friends, or deepen some of the connections you already have.

But first let’s talk about Hepzibah. It sounds as if you are considering getting in touch with her because you are lonely for real closeness. Fair enough, but you would be taking a risk. From the little you have told me it sounds as if she may not be the best person to cultivate, or re-cultivate, as a close friend and confidante – not just because of the affair, although that certainly counts for plenty, but also because of the cruelly ill-timed and unapologetic way she told you about it. Some friendships, like many marriages, can survive a triangle and a betrayal. And it may actually help that Carl is no longer around to put Hepzibah’s loyalty to the test. But if I were you I would think twice before you start to count on her again. If the closeness you had, and miss, stems mostly from familiarity, shared experiences, and the like—boring, reliable stuff, except of course where the shared experience was Carl!—it might make sense to meet again, but with low expectations and eyes wide open. Then, if conversing worked out, you could slowly and carefully resume some of your former shared activities.

I would be far more reluctant to reconnect if what you miss is something more visceral and volatile: Do you long for her because she “gets” you? Because she has always been such a charming, though difficult, person? Because she used to enliven your dull existence, and you can see why Carl fell for her? You are at a vulnerable time in your life, and you should not set yourself up for emotional dependence on somebody who might keep letting you down.

So, as regards Hepzibah, I advise you to think about why you are considering a rapprochement and then, based on how you assess your motives, move slowly, or not at all. If you do resume your friendship, you may find that Hepzibah is not really the linchpin friend you thought she was, at least not any more. Or you may slip back into something like your old friendship, and find that its reflected warmth makes your other, shallower local relationships more satisfactory. But this, I suspect, is a long shot.

Whatever happens with Hepzibah, you should definitely try to form other close relationships, and nurture the ones you have. Here are some ideas:

See if your friend in Japan is open to more frequent letters, a regular schedule of phone calls, video connections, maybe even a visit if you can afford it. If she is as good a friend as you say, you can make her understand how important this contact is to you now.

Think about the couples you know. Could you deepen your friendship with any of them by socializing and conversing as a trio? From what you wrote, this sounds unlikely, but it can happen. Are you independent friends with any of the individuals in these couples, or would you like to be?  If so, take the first step, and maybe the second.

Are there any neighbors, parents of your kids’ friends, or other acquaintances-of-convenience you think might be worth bumping up to real friend?  Seek them out. This is hard, I know. But you may find that they are receptive, even flattered, and one or two of them may turn out to be serious friend material.

I have found that, as with happiness in general, the best way to find friendship is not by seeking it directly and exclusively, but as a by-product of some other worthwhile endeavor such as a serious book club or (if you are a writer) workshop, political activity, class, or public service. For example: If you are not in a book group, join one. If the one you join, or are already in, seems insipid, join another one. See if any of the members are worth picking off the herd and, if so, think of some way to talk one-on-one without making it a big deal—like carpooling, or a short weekday lunch. If you love art or music or some sport, and are good at it, find a place to improve or practice it at the highest level you can manage. This gives you better odds of a congenial pool, as well as something to talk about. And from what I have seen of this season’s political campaign, many war buddies are emerging from the fray. Charitable and support groups are another way to get to know people in the context of serious conversation and shared experience. Have you thought of joining an Alzheimer’s-related organization?

If this sounds depressingly like looking for romantic love, I suppose it is; but I hope that looking for friendship is less generally fraught. (Come to think of it, although it is a bit early and you may not be interested, you could in fact find romance. Happy accidents do happen.)

It gets harder to make close friends once we don’t have school or, to a lesser extent, kids to throw us together. The process can be terribly hit-or-miss and unpredictable. But it is worth it when real friendships do develop within the world you currently inhabit. I know this from experience.

One last thought: you have lost and endured so much this year. You must still be shocked and grieving, and you may also be depressed. All this could be coloring your perceptions of the people who remain in your life and your vicinity. Maybe some of them are less shallow, and already closer friends, than you think.

Dear June,

I have been dating “Leo” for about three months now. We spend the night together two or three times a week, but always at his house because I have a cat and he cannot stand cats. I would usually rather stay at my own place. It’s nicer there, it’s more convenient for me if I have to go to work in the morning, and, well, there’s my cat. But I have been putting up with it because I like Leo and he has really given me no choice.

I never truly insisted until yesterday, but last night I put my foot down and said that if we were going to be together overnight it would have to be at my place because Wystan had an ear infection and I had an early meeting with my boss. Leo simply refused. So I asked him—just theoretically, neither of us is at that point—what would happen if we ever moved in together. He smiled as if he was saying something cute and said: “You already know the answer—it’s me or the cat.”

He says that he is not allergic. He also says that he doesn’t have a phobia or anything. He is just a macho guy, he says, not a cat kind of guy, and he hates being around them.

I am actually thinking of breaking it off with Leo, all because of Wystan (and any future Wystans). Am I a crazy cat lady?

Ailurophile in Altoona

Dear Aily,

Not at all.

You have been dating Leo for all of three months, and you do not seem to have gone beyond “liking” him. At this stage in your relationship it may be slightly unusual, but it is certainly not crazy, to decide that you prefer a future with Wystan (and his successors) to a future with Leo. And that would be true even if Leo had a good reason to object to Wystan, such as an allergy or a true phobia.

But Leo has not given you a reason nor, apparently, has he even considered your point of view or your affection for Wystan. Your boyfriend sounds dictatorial and insensitive, all cats aside. And his remark about being a macho kind of guy would alone give me pause. Do you really want a man who prides himself on machismo? Or one so ignorant that he apparently thinks that cats, the tribe or the tiger, are an affront to masculinity? Has the man ever gone one on one with a pissed-off cat? I do so almost daily, and my cat makes most dogs and many men look like pathetic wimps.

But I digress. Seriously, Aily, I would think twice before getting in any deeper with a bossy soi-disant macho man who won’t even discuss ways you might stay together in the future without your losing your beloved pet. Talk to Leo if you must, and if he will. Maybe he will explain himself more satisfactorily if pressed. Maybe he will even bend a little once he sees that you take this issue very seriously. But I have my doubts and, all things considered, I think you might turn into a crazy catless lady if you stay with him.

You sound like a warm, clever person. You make up good names, and you are obviously sound on Auden, whom so many people have unaccountably been badmouthing recently. I bet you can do much better than macho Leo; it would be a shame if you gave up Wystan before you figured this out.

Cleaver’s in-house advice columnist opines on matters punctuational, interpersonal, and philosophical, spinning wit and literary wisdom in response to your ethical quandaries. Write to her at [email protected]. Find more columns by June in her attic.