Mallory Ortberg’s Favorite Advice Columns

Last year, I became an advice columnist. This is my only qualification for being an advice columnist, as I am quite literally just some guy. “Noted some guy Mallory Ortberg.” Here are a few of my favorite advice columns:

1. “The Monty Hall Problem” (Marilyn vos Savant, Parade Magazine)

Priceonomics describes this column thusly:

When vos Savant politely responded to a reader’s inquiry on the Monty Hall Problem, a then-relatively-unknown probability puzzle, she never could’ve imagined what would unfold: though her answer was correct, she received over 10,000 letters, many from noted scholars and Ph.Ds, informing her that she was a hare-brained idiot.

What ensued for vos Savant was a nightmarish journey, rife with name-calling, gender-based assumptions, and academic persecution.

2. “I racked up $20,000 in personal charges on my company credit card: update” (Ask A Manager)

I love Ask A Manager. I love the wave of relief that washes over me when I read about someone else’s trainwreck. The best part is that things sort of worked out! This guy was just horrified and knew he’d made a horrible mess and felt like he could never tell anyone or find a way to fix it, and he was honest, and he faced the consequences, and they figured out a solution. Sometimes you get to see someone slice the Gordian knot!

Remember the letter-writer last month who had racked up $20,000 in personal charges on his company credit card and was in a horrible cycle of using the card to take Paypal cash advances to pay it off each month, thus moving it to the next month, along with interest charges? Here’s his update.

I went to my manager and just laid it on the table, cut out any mention of factors as to how I got here, just laid it out: I have $20k personal expenses on the company card and I can’t immediately pay it back.

He had to go to his boss, and she had a teleconference with me, along with HR. Along with the meeting invite, they attached the company credit card policy, along with the ethics policy.

The first question they asked was, “Do you understand how a company card is supposed to be used?” I said that I have read the documents they gave me, and from reading them and talking to my manager it is very clear that the way I have been using the card up until now is inappropriate.

3. “Brotherly Love” (Emily Yoffe, Dear Prudence)

This one is an all-time Hall of Famer, no question. (I should mention I have no interest in arguing over whether or not a letter is fake.) It’s gay incestuous twins. And it’s uncomfortable and odd and a little sad and a little lovely! Emily is a wonderful mix of practical and gentle here. Who knew twincest could tug on the heartstrings?

My fraternal twin and I (both men) are in our late 30s. We were always extremely close and shared a bedroom growing up. When we were 12 we gradually started experimenting sexually with each other. After a couple of years, we realized we had fallen in love. Of course we felt guilty and ashamed, and we didn’t dare tell anyone what we were doing. We hoped it was “just a phase” that we’d grow out of, but we wound up sleeping together  until we left for college. We knew this could ruin our lives, so we made a pact to end it. We attended schools far apart and limited our contact to family holidays. But we never fell out of love with each other, so after graduation we moved in together and have been living very discreetly as a monogamous couple ever since. I’m not writing to you to pass moral judgment on our relationship—we’re at peace and very happy. Our dilemma is how to deal with our increasingly nosy family and friends.

4. “Ask Ijeoma” (The Establishment)

It’s a new advice column, but I love Ijeoma’s other work and I’m excited to see where it goes.

I think that we need to stop looking at relationships like property and start looking at them as agreements. You are with someone because you want to be, and if you are monogamous, it’s because you choose to be. Nobody is “taken” by anybody—it’s impossible. You are your own person all the time, and you are solely responsible for your decisions. Does this mean that a woman shouldn’t feel bad if she starts a relationship with someone who already has a partner, or even a family? Honestly, I don’t know if it matters. Because if you’ve been hurt by an unfaithful partner, your pain isn’t that someone was willing to sleep with your partner, your pain is that your partner was willing to sleep with someone else.

5. “Miss Lonelyhearts” (Nathanael West)

The Miss Lonelyhearts of The New York Post-Dispatch (Are-you-in-trouble? –Do-you-need-advice?–Write-to-Miss-Lonelyhearts-and-she-will-help-you) sat at his desk and stared at a piece of white cardboard. On it a prayer had been printed by Shrike, the feature editor.

“Soul of Miss L, glorify me.
Body of Miss L, nourish me
Blood of Miss L, intoxicate me.
Tears of Miss L, wash me.
Oh good Miss L, excuse my plea,
And hide me in your heart,
And defend me from mine enemies.
Help me, Miss L, help me, help me.
In saecula saeculorum. Amen.”

Although the deadline was less than a quarter of an hour away, he was still working on his leader. He had gone as far as: “Life is worth while, for it is full of dreams and peace, gentleness and ecstasy, and faith that burns like a clear white flame on a grim dark altar.” But he found it impossible to continue. The letters were no longer funny. He could not go on finding the same joke funny thirty times a day for months on end. And on most days he received more than thirty letters, all of them alike, stamped from the dough of suffering with a heart-shaped cookie knife.

Honorable Mention: This scene from the season 3 “Simpsons” episode, “Like Father, Like Clown”:

Man Seeking Advice #1: Reb Krustofsky, should I finish college?
Rabbi Krustofski: Yes. No one is poor except he who lacks knowledge.
Mother: Rabbi, should I have another child?
Rabbi Krustofski: Yes. Another child would be a blessing on your house.
Man Seeking Advice #2: Rabbi, should I buy a Chrysler?
Rabbi Krustofski: Could you rephrase that as an ethical question?
Man Seeking Advice #2: Um… is it right to buy a Chrysler?
Rabbi Krustofski: Oh, yes. For great is the car with power steering and dyna-flow suspension.

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Mallory Ortberg answers advice at Dear Prudence, is co-founder of the Toast, and the author of Texts From Jane Eyre. Follow her on Twitter.