When Should You Tell Someone About an Affair?

Dear Lisa,
I recently learned that the son-in-law of one of my closest friends has been having an affair. This man and my friend's daughter (whom I love) have three kids and what always appeared to be a pretty nice life together. Do I tell my friend?
— Between a Rock and a Hard Place

Here's the deal, Rocky,
What we've got is a no-win situation. If you stay quiet, you feel complicit; if you speak up, you risk doing far more harm than good.

So while there's no clear-cut solution, there is one course of action that's preferable: Don't say a word to anyone. To begin with, it could be that your friend's daughter already knows and is trying to handle things privately—or at least without any involvement from her mother. It could also be that his cheating heart will come to its senses before his wife finds out, in which case you could end up hurting a lot of people for what may have been no more than one terrible transgression. Finally, nobody ever knows what's really going on inside someone else's marriage; perhaps these two have some sort of "don't ask, don't tell" arrangement. Are any of these scenarios likely? I don't know, and neither do you. The point is that they're all plausible—so keep quiet.

If, however, you just can't bring yourself to leave bad enough alone, then there's only one person to approach, and that's the cheater himself. The trick is to avoid phrases like "Burn in hell, slime monkey" and "Drop dead, you selfish rat bastard." Instead, you might try extolling the virtues of a good therapist who can help this man pinpoint the deepest sources of dissatisfaction in his life and lead him toward a healthy way to deal with his issues before he loses everything—including, but definitely not limited to, the trust and respect of his three children.

Dear Lisa,
I don't have a baby, but I do have a dachshund named Manolo, whom my friends complain I treat like a baby. He's got a special seat belt in the car, I hire a sitter if I'm going to be out super late on a Saturday night, and I often cook him dinner. I guess I do sort of think of him as my baby boy. Does that sound nutty to you?
— Crazy Dog Lady

Oh, Sweetie,
If it's nutty to want your pet to be safe, happy, and healthy, then we need to find a padded cell with room enough for both of us. Not only do I cook my beloved Waffle (known in some circles as Captain Velvet Tummy) a well-balanced meal every night, but I have occasionally considered serving it on Hermès china as a roving violinist serenades him with the score from South Pacific.

Let's cut to the chase: They say you can't pick your family, but I don't buy that. There are all kinds of ways to have a family, and believe me, you could do a hell of a lot worse than little Manolo (a concept I will explore more fully in my upcoming "So Your Aunt Ida Thinks You've Put On a Few Pounds" column). It would be one thing if you were using your darling dachshund as an excuse to avoid getting out there on a Saturday night, but it sounds like that's not a problem. The only thing Manolo seems to do to your life is enrich it.

Dear Lisa,
Is it the worst thing in the world to take a handicapped parking space if you're just ducking into a store for five minutes? Did I mention it was pouring?
— Dry in Dallas

Dear Rainy Day Woman,
Disease, famine, genocide, and that sequel to Paul Blart: Mall Cop are the worst things in the world. Taking a parking space from someone who truly needs it comes in at number five, just above the sound of a pan flute solo. Until rude behavior is officially reclassified as a disability, you need to find another space.

Lisa Kogan is O's writer at large and the author of Someone Will Be with You Shortly: Notes from a Perfectly Imperfect Life. To ask Lisa a question, email asklisa@hearst.com.