Dear Carolyn:

I have a daughter in her mid-30s. When she was in her 20s, she always said she would be married by 30. Recently she said she thinks she'll be an "old maid" (her choice of words), principally because there are no suitable men available in her age group.

What can I say when the conversation comes up again -- something that would be supportive, nonjudgmental, not insult her intelligence with the usual platitudes, but something that does not reinforce her point of view? I don't agree with her -- and no, I do not have a crystal ball.

-- Atlanta

I don't agree with her, either, but my predictive powers have nothing to do with it, since she may well never marry. Where I disagree with her is on her view of unmarried women.

And single men, for that matter.

And married ones, too, of both sexes.

And her ageist approach to dating.

Did I leave anything out?

I can unclutter my objections by packaging them into one overarching beef: I have a real problem with the whole concept of "should."

Your daughter's dangerous romance with Should was in full bloom in her 20s, when she saw a husband as something she should have by 30.

Then, the romance started to sour when she, still unmarried, held on to an idea of the type of person a husband should be. Your letter refers to age, but rigid ideas are like cockroaches; how often is there only one?

Then, the romance with Should turned abusive when she started to see herself -- and therefore, by logic, others in her cohort, male and female -- as outcasts, failures of a Should society. Her self-loathing also grants undeserved status to the married, who are no more inoculated against lonely wretchedness than singles are doomed to it.

The way you phrase this to your daughter is a matter of your emotional style and hers. However you choose to say it, though, please challenge her Should-centric worldview. The idea of playing the hand we're dealt is such a cliche that it's easily dismissed -- yet I can be a total stranger to your daughter and still say with confidence that she's suffering not from a paucity of men, but from her own flat refusal to look at her cards as a challenging puzzle, if not an outright gift.

She may not -- hehhh, likely won't -- listen to you, certainly not the first time, and you can't push her to see herself in a new way. But you can make sure, each time, gently -- "I'm proud of the choices you've made" -- that her dehumanizing view of un-paired-off people won't stand.

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Dear Carolyn:

Recently I snooped through my boyfriend's email, text messages and phone calls. I had a funny feeling, and then unexpectedly got the opportunity to do it. I'm not proud of what I did, but I guess what's done is done.

I found that he has been talking to his ex around two or three times a week through texts, emails and phone calls. They don't talk about much, work, mutual friends, etc. (neither I nor the ex's boyfriend is brought up).

However, what I find most shocking is that my boyfriend contacts her most of the time and I find myself actually feeling some ADMIRATION for the ex because she does blow him off a lot. He broke up with her, and not well (from what I understand), but who does? What do I do with this information? Confront him or sit on it? Is this a sign he is unhappy in our current relationship? I have tried talking to him about how he feels in the relationship and if anything is bothering him. He admitted to having a hard time at work recently but nothing about the ex.

-- Regretful snooper

This is a binary choice, but the two parts aren't "confront him" and "sit on it." They're a much broader "tell" or "don't tell," umbrella terms that allow for a lot of ways to tell (and to keep quiet), including confront, declare and confess, among others.

When deciding what to do, please consult the confess/admit/concede part of the thesaurus. Silence is a lie, and accusing him brushes past your error with a lightness it doesn't deserve -- as your letter arguably does.

More important, though, staying quiet and accusing him both miss the point. You don't want to hide your infraction or put him on the defensive about his; what you want is to find out what's going on. Between them, sure, but only as it illuminates what's going on between you.

When you're snooping because something between you is off, and when he's pursuing a covert friendship with his ex despite some resistance from said ex, saving or ending the relationship has to be seen as an ancillary concern. The main one being, can you tell each other the truth? That's the only happy ending you want.

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