Dear Lisa,
My 16-year-old son gets excellent grades, does plenty of chores, and helps his younger sister. But he recently got into a drunken brawl with kids from another school. The police were called, and Rob was arrested. Nothing even remotely like this has ever happened before. My husband insisted on “teaching him a lesson,” so he let him cool his heels in jail for two days. Was that the right thing?
—Janet, Connecticut

Here's the thing Janet,
I believe that letting a 16-year-old sit in jail for two days teaches him one lesson only: If there’s ever serious trouble, he can’t count on his mom and dad. I know this was your husband’s attempt at tough love, but leaving a hungover teen to fend for himself in jail for 48 hours has potential disaster written all over it. I guess I’d have picked him up, told him to shower, asked him to explain exactly what happened, listened carefully, and reminded myself that every kid does something wildly stupid at some point. I would’ve proceeded to be incredibly grateful that he was in one piece, talked to him about alcohol abuse, hugged him for a long time, and taken away every privilege he’s ever received, including—but not limited to—car keys, computer, and phone for approximately 60 years.

Dear Lisa,
I brought a very good friend, whom I've known for many years but seldom see now, to visit another friend. Two weeks later, the second friend told me my good friend had stolen something small but valuable from him during our visit. I was shocked and said that was impossible but he remains adamant. I'm not going to mention this to my good friend, and I don't plan to say any more about it to the accuser. Would you have handled this differently, and do you have some advice on settling my discomfort?
—I would rather you did not use my name or state

Dear Jane Doe from planet Earth,
I would have handled it exactly the way you did, but with more awkward stammering. As for any subsequent discomfort you may be feeling, my advice would be to self-medicate until all is forgotten. No? Okay, then how about reminding yourself that you’ve done absolutely nothing wrong. You’re a loyal friend in a world where loyalty isn’t always easy to come by—and that, Ms. Jane Doe, should become your discomfort-alleviating mantra.

Dear Lisa,
Joe, my husband of four years, loves to climb and fish, while I love museums and theater. Every year we take separate vacations, and every year our friends and family are convinced the marriage is crumbling. My cousin even took me to lunch to let me know I’m “better off without him.” We’re very happy together—and very happy apart. Must I scale Mount Rainier and catch a trout to shut everybody up?
—Nina, Omaha

Dear culture-vulture,
If Joe isn’t up for the latest David Hockney retrospective and you’d prefer not to start interviewing for a good Sherpa, then dammit, I say more power to you! Frankly, if you decide to have children, the whole red snapper versus Rembrandt thing becomes a moot point because all trips will somehow involve a family selfie with Daisy Duck. For now, perhaps a group email is in order:

"To whom it may concern,
In the interest of clarity, we’d like to inform you that once again, the two of us will take separate vacations for approximately 14 days in the spring of 2018. While Joe has nothing against a good Sweeney Todd revival, and I have long enjoyed all manner of Timberland footwear, neither of us can get excited enough to justify two weeks of schlepping through the other’s adventure, yet we are secure enough in our love that we genuinely wish each other a fantastic holiday. Additionally, we are pleased to announce that we have agreed upon our safe word for the absurdly kinky, white-hot sex we’ll be having upon our return.

On another note: Shall we shoot for Christmas at our place this year?

Nina and Joe"

You may want to do some light tweaking, but ultimately, this is exactly the kind of email that takes the questions somewhere else entirely.

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


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