The 3 Best Advice Column Questions

Advice columns are windows into other people’s lives

I am an advice column addict.

I read three or four a day, bouncing from one to the other trying to figure out when I’ll get my next hit — “Well, she always posts on Thursdays — and this one normally has a new post every Tuesday — and I haven’t read the full archive of that one yet.”

I’m not entirely sure what the root of my obsession is. But I think I’m drawn to a world in which a sensible person is sought out by people with disastrous lives, so she can preach the word of Rational Decision Making and Common Sense to a willing audience. Like virtually everyone I know, I have a crowd of acquaintances whom I’ve seen essentially torching their lives with an incendiary mixture of bad decisions and worse attitudes, and I’ve longed to shake them by the shoulders and talk sense to them. In the world of advice columns, those friends are asking someone to shake them by the shoulders and talk sense to them. It’s so satisfying.

Advice columns normally fall under one of two categories: tips on manners and etiquette, and “Holy sh!t what is wrong with your life?!” I mostly read the latter. Sometimes I even skip the advice.

If advice columns were only about dispensing advice, there’d be no need to even print the questions; columnists would just write once or twice weekly with the same general rules for living that they parcel out, piecemeal, in response to their letter writers. If you read as many as me you start to notice each columnist’s go-to wisdom bombs. Kapow! You need to let the past go. Boom! Communicate, don’t seethe in silent resentment. Zap! Leave your stinking cheating dead-beat boyfriend.

I don’t judge or dislike my favorite columnists for recycling their wisdom; it wouldn’t be wisdom if it only worked once.

But you also have to admit: if everyone followed it, would everybody be a little happier? Probably… a little. There’s another part missing from the equation of life satisfaction that doesn’t have to do with making all your decisions on a solely rational basis.

The following is the list of three of the most genre-defining, convention-bending, head-scratching, mouth-gaping advice column questions and answers. There are plenty of outrageous (and probably fake) questions out there, so these weren’t chosen purely on the basis of Jerry Springer worthiness; they’re the questions that made me ask, “Why do people seek advice from strangers?” “What does this question and answer say about our culture?” and “Why haven’t you talked to your parole officer about that?”

Live a little more like Blondie?

#3: “Should I ditch my life and move to L.A. to become a singer, or stay for love?”

In this column by Amy Alkon, aka the Advice Goddess, a 25-year-old aspiring singer writes about how committed she is to throwing her whole life into music, until she drunkenly hooks up with the drummer of her band a week before moving to The Big City, and suddenly has second thoughts. She knows her plans don’t involve a relationship, he doesn’t appear to seek one, but without warning she’s full of confusion about what she really wants from her life.

Alkon tells her, sensibly, that some of her feelings are probably due to what I like to call “sex brain” — the physiological reaction that people experience after sex that encourages bonding. She then goes on to advise the letter writer,

Now, with big scary life changes looming, maybe it’s tempting to find a reason to stay where you are. You need to decide who’s the boss here — your ambition or your feelings.

In other words, there’s no single “right” choice in this decision. And I have to admit, I’m rooting for both options. On the one hand, there’s the artistic flight to the West Coast to pursue her dreams and adventures. On the other, there’s the thrill of new romance, the tingle of possibility, the intoxication of following the heart’s impulses — and the refreshing jolt of reevaluating her goals and desires.

One thing unites both choices: they’re full of risk and uncertainty. And that’s what makes Alkon’s answer so different from the archetypal advice columnist’s. Alkon isn’t instructing the writer on the most sensible, pain- and uncertainty-free way to live her life. If that were the case, I’d tell the letter writer to stay home and steer clear of the flaky drummer. It’s the most conservative path.

Life without stupid decisions is like subsisting entirely on a diet of undressed green salad. It’s probably really good for you. But it still sucks.

Do I envy the people who write in with crippling, haunting, sometimes life-threatening problems? No. But do some problems — sometimes, in some cases — actually make it sound like the letter writer is just living her life more thoroughly than I am? A sheepish yes. “You quit your job, ditched your friends, sold all your furniture and moved to Los Angeles to become a singer? What is wrong with you?! And where do I sign up?”

I understand what drives people to seek advice; and also what compels me to give it so prolifically (sometimes my friends call me their unofficial therapist). When seeking advice: I don’t just want to be told what the best course of action is, I also want to abdicate a little bit of my responsibility to make a choice. I feel safer following directions than making them up on my own. When giving advice: I seek order, and I want to see my friends follow my specific instructions to achieve it so their lives will unfold in a logical, soothingly predictable way. I want to protect them from getting hurt, which often means protecting them from uncertainty or volatile circumstances.

Neither of these is an especially noble impulse when you look at it. The first should seem obvious. And the second — well, it’s natural to want to protect people you love from pain, but sometimes the best thing to do for a friend is support her as she embarks on something scary, new, and unpredictable, because life is scary, new, and unpredictable, and if you never encounter anything scary, new, and unpredictable, you probably aren’t really living it.

I want to write an advice column in which I go with the opposite of my advice-giving instincts, and encourage people to expand their horizons, goof off, and make a bad decision every once in a while — the kind of little bad decision that leads to a better life.

#2: “How do I tell my family I’ve been in a relationship with my twin brother…for decades?”

In terms of overturning tradition, Emily Yoffe (Slate’s “Dear Prudence”) upped the ante by giving what many readers saw as a tacit endorsement to a gay couple of twins in an incestuous relationship. One of the twins wrote to her describing his lifelong relationship with his brother, and how — now deep into middle age — they weren’t certain how to field questions from well-meaning relatives wondering why they weren’t each seeking a mate, but were content to be seemingly single “roommates.” Yoffe’s reply offered gentle advice on how to break the news to the men’s family — without seeming to judge their living situation.

Obviously this question elicited one of the most intense “What the frack?!” moments of my advice-column-reading life. But the meaningfulness of this question and response goes deeper than just its shock value.

Later, in response to another letter writer, Yoffe defended her answer by saying the original couple weren’t asking her if their relationship was right or wrong, but simply how to tell their family about their decades-long relationship. She then strongly advised the new letter writer (who was on the cusp of an incestuous relationship herself) to back away from forming such a relationship before things went too far.

Emily Yoffe is no Dan Savage — readers don’t turn to her for edgy, convention-smashing sex advice, so this episode stood out — so much so that she’s still discussing it, nearly a year after the letter originally ran. But she and Alkon stand for the new wave in advice columns: instead of tutoring advice-seekers on how to best conform to conventional behavior (an all-over life application of the “manners and etiquette” approach), advice columnists are teaching advice-seekers how to be comfortable in their own skin, honest about their own desires, and confident in their unique choices, even if they’re a little off the beaten path. They don’t give advice on etiquette so much as a philosophy of happiness.

Recently I’ve noticed a trend among the more cutting-edge advice columnists (in the “Holy sh!t what is wrong with your life?!” category) to urge letter writers less toward a discrete course of action and more toward honest self-examination. In other words, there isn’t a right and wrong answer to every question — an odd admission in a genre that got its start by telling people the right and wrong things to do. Instead, these columnists are acting like a magnifying mirror with a high-powered light for the letter writers: here’s an unvarnished look at the reality of your situation, now ask yourself what you really want.

This can be a good and a bad thing. It’s a good thing, in that it encourages a fuller and more satisfying life through honesty. But it gets murky when such advice is unmoored from a moral standard. But where’s the line? And what do our standards mean?

On a milder note (in terms of content — certainly not in snark), one writer sent an age-old question to Amy Alkon: should I leave my boyfriend, who loves me but seems unwilling to get married? A traditional advice dispenser might have given her a simple “He’s a loser, run for the hills!” But Alkin takes a more nuanced approach:

Everything you say about the guy screams that the only aisle he’ll be walking down anytime soon is one with a big sale on Tostitos or beer. This doesn’t make him a bad person — just a bad person to be hitting up for a marriage proposal. … Yes, getting married is supposed to be the ultimate way of showing love and devotion, and maybe that’s why so many people do it four times. You need to ask yourself: Are you more in love with the guy or the idea of marrying the guy?

Alkon’s advice overturns the old-fashioned view that marriage is the end game of every relationship and the goal of every woman in one: instead, she urges the writer to figure out what she wants in her relationship and her life — but above all, to be honest with herself about her situation.

Instead of giving the advice seeker a set of instructions, columnists give her a set of choices. And the reader’s lingering curiosity is no longer “Did she do it?” but “Which did she do?”

In my new advice column, I won’t give answers, but choices.

#1: “How do I thank the people I love before I die?”

Dear Abby is the queen mother of advice columnists, her legacy carried on by her daughter. It seems especially fitting, after her recent death, to including this moving letter to the column that she founded:

DEAR ABBY: I have enjoyed a good life. I have served my community. I have a wonderful wife, great children and good friends. However, it now appears that the disease that has been kept at bay has progressed, and soon my days will end. I have accepted my impending death as best one can, and let few people know of it.I would like to thank all the wonderful people who have been an important part of my life over the years, and I’m wondering how that might be accomplished.

It’s not a shocking letter. It doesn’t contain any juicy complaints about ridiculous relatives or bad behavior. It’s certainly not calculated to maximize pageviews with its controversy. So why did Dear Abby run this letter? And why am I featuring it here?

Because it’s about kindness. Selfless kindness. A man is facing his last days and the question he chooses to send an advice columnist is about how to thank all the good people in his life. This kind of question is rare in advice world. First of all, it lacks the zing — the potential for outrage — that keep lots of readers (like me) coming back for more every week. Secondly, it’s rare among advice columns because it’s rare among people.

We are selfish creatures. When given the opportunity to air our grievances and beg attention for our insecurities in a starkly public forum, we can’t say enough about ourselves. Somewhere in the bilge of petty, sniping, self-absorbed questions, Dear Abby chose to run one about treating others kindly, putting their needs first, and being considerate of their feelings. In another recent column, she ran a letter which was not a question but a reminder to readers to include the lonely (and alone) people in their lives in their Valentine’s Day celebrations. It was heartwarming, and not in a hokey way — it was inspirational.

That’s where I think Dear Abby was the closest to finding that line between encouraging people to be themselves, while remaining moored in moral philosophy. Dear Abby wasn’t all about conforming to current social norms (after all, when a couple wrote to her asking how to improve their neighborhood after a gay couple moved in, she famously quipped, “You could move.”). Her morality wasn’t conventional. But at its heart was kindness. And for as many fascinating advice columns there are about self-actualization, her advice seems the most steadfast, timeless and universal: let kindness be your guide.

I was tempted to include, as the ultimate advice column question, one of the absolute bombshells sent to Alkon, who’s a personal favorite of mine for her snark, her libertarian viewpoint, her scientifically informed advice, and her truly bizarre and entertaining menagerie of letter writers. Three that I were considering were the Occupy shaman hippy chick seeking advice on whether to stay with her plain as peanut butter and jelly boyfriend, the woman who was convinced the man who jilted her was her soul mate in a previous life, and the woman who wonders why her obviously gay or asexual boyfriend is so vehemently opposed to having sex with her.

Those are still worth a read, first of all because they’re hilarious — and secondly, because they’re such a perfect counterpoint to Dear Abby’s non-self-absorbed letter writer. Alkon’s most ridiculous three writers don’t just suffer from the problems they seek advice on — ultimately, at the root of their unhappiness and dissatisfaction is probably the utter self-absorption that led them to get into those situations in the first place. It’s not Alkon’s gig to judge them for that (though she does get a hilarious jab in every once in a while). But I don’t think an advice columnist could go far wrong by encouraging all their writers and readers to be kinder, more considerate, less self-absorbed, and more outward-looking in their lives.

I hope to use a new advice column here at PJ Lifestyle to encourage people to both treat each other a little better as well as make better decisions about themselves.

Advice columnists don’t just dispense do’s and don’ts. And they don’t just advise on the most rational course of action — many of them coach readers to figure that out for themselves. So why not write an advice column that doesn’t have anything to do with rationality at all, but has more to do with possibility? Kindness? And experiencing life to its fullest?

That’s the kind of column I’m interested in writing. I’m a rational person. I also tend to think the thing many advice seekers most sorely need is a glaringly honest look at themselves and their own flaws. There are a dozen other advice columns out there to tell readers what the “right” thing to do is, or even the right way to figure out what the right thing is for them as an individual. I want to write an advice column about possibility.

In my recent post about Lana Del Rey, I wrote about numbness as a plague of my generation, the “Millennials.”

We were shoved into college, pushed to be high achievers, just when colleges started to fail us — and cost a lot doing it.

We’re isolated more and more even as we think we’re more digitally connected — finding more meaningful relationships with a phone than with a person.

We’re underemployed, and the meaning and satisfaction that a successful and stable career seemed to give our grandparents is closed to us now. Many of us are “going Galt.”

We spent the first 22 years of our life filling out assignments and following directions in school, and then feel hollow and afraid when we’re shunted into the adult world and told to make our own decisions.

I’m not writing this to beg for pity for Millennials — I’m writing this to Millennials, in the hope that they realize the biggest impediment to their happiness is their own attitude. Put down your phone. Take control of your life. Find ways to occupy yourself. Let go of your fears and have an adventure. Don’t be a victim of circumstance, a martyr to your age.

I’d like to write an advice column where, instead of telling everyone how to do things correctly to manage their lives with as little chaos and pain as possible, I instead teach them how to relax a bit and fear life a little less, how to be open to all the possibilities of kindness in their lives, and how to find meaning in the simplest acts. Then maybe along the way I can learn to do a little bit of the same in my own life.

PJ Lifestyle’s Bad Advice column is by a Millennial, for Millennials. I’ll answer your questions with wisdom and honesty, and I’ll try to tell you the most rational thing to do. But then I’ll tell you about a few irrational options, too — the “bad” advice. Ones that might help you break out of your comfort zone and attempt a little calculated risk. It’s an experiment I hope you’ll participate in. Send your questions to [email protected] and share this with your friends. If you think my answers are dumb, you can have a hoot kicking them around in the comments. I look forward to hearing from you.


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10 Years After High School Are Millennials Finally Ready to Cash Their Reality Check?

The Plan So I Don’t Waste the Last Year of My 20s

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The Source of Both Infinite Happiness and Meaning