Dear Prudence

The Truth About Charlie

Prudie counsels a couple who want to give their daughter a “boy’s name.”

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Hello, denizens of Slate! I wanted to say hello before we got started on today’s chat. It still feels entirely surreal to be participating in the live chat I usually pore over during my lunch break. I’ve been a fan of Emily Yoffe’s Prudence for years and trawled the archives to the days of Margo Howard and beyond whenever I was caught up on the latest installments. So I’m excited and more than a little nervous as I jump in at the end of Emily’s tenure.

I’ve long loved Dear Prudence for the sheer variety of human experience on display, but there’s so many reasons to read beyond the selfish pleasure of emotional rubbernecking. Emily’s answers were always kind yet bracing—neither excessively gentle nor overly dismissive. I particularly appreciated her stance on forgiveness and the idea that it’s not a requirement in every situation. As she wrote in her final chat:

It’s true that I took a hard, critical look at forced forgiveness. I am not against forgiveness! But too many people are bullied into it. I also disagree that without forgiveness one is stuck. No, it’s perfectly possible to not forgive but to also accept what happened and move on.

It’s such a lovely distillation of what Emily brought to the column: critical thinking and appropriate boundaries for everyone!

I’m both thrilled and apprehensive at the prospect of being the next advice-giver to step in. I have no intention of trying to fill Emily’s shoes; I’ve brought my own with me. I can be only myself. It is my hope that I can strike a manageable balance between empathy and humor, thoughtfulness and light-heartedness, to take others seriously without giving in to self-seriousness. (Wish me luck with that, won’t you?)

Here’s a bit of biography, sticking only to the highlights, so you don’t have to be completely in the dark about who is flinging advice at you:

  • I’m 28 and live in Oakland, California, in a house with a very old dog and an even older cat.
  • Neither the dog nor the cat contributes in any significant financial way to the household
  • I vote and floss regularly, as the situation calls for it.
  • I once saw a bone-white pigeon in the street, which is to say that I’ve seen things you wouldn’t believe.
  • I’m anxious to do my best as Dear Prudence.

That’s enough about me for now, I think. I’m eager to get to know all of you. Let’s chat!

—Mallory Ortberg

Q. Baby Name Rudeness: Welcome, Mallory! My husband and I are expecting a baby girl and have chosen the name “Charlie.” I realize this is a slightly unconventional name for a girl, but I think it’s adorable. As we have started sharing the name, we have gotten more than one rude comment (usually from acquaintances or strangers who ask). These comments are generally along the lines of: “For a girl?” or “Wouldn’t you like to save that name for a boy?” What is the best way to respond to these comments? I want to let people know that they are being inappropriate and rude, but I don’t think saying, “What the hell is wrong with you?” (what I’m thinking) is the best response.

A: I always wonder when people say something like, “That’s a terrible name” to a stranger describing her yet-to-be-born child. What’s their projected outcome? “Ah, I see how terrible that name, which I liked enough to give my child five seconds ago, is now. Thank you. I shall name my daughter after you and send her to you for seven years of service when she becomes a woman”?

I think Charlie’s a nice name. Leslie used to be a boy’s name, and look at where that got Leslie Howard. (Well. He died a hero’s death during World War II, but you see my point.) They’re not thinking is the answer. They’re blurting out the first thought that comes into their heads, and a simple, “Well, we like it” should be enough to clue in all but the most thoughtless. You could get into a fight every time a work acquaintance declares he doesn’t like your daughter’s name, but that seems like a misuse of your time. There’s always a way to say, “Well, we like it” in such a way that the “What the hell is wrong with you?” is clearly implied. It’s chiefly in the way one holds the chin while delivering it in as bland and uninterested a tone as possible.

Q. This Is Nicole, Your Business and Life Partner: Dear Prudie, 
you look really pretty in that picture. I hope you are having fun doing your first chat!

A: This is a softball of a question, and I am more than a little insulted by the implication that I cannot start this live chat without assistance from my Toast co-founder.

I will also take it. Thank you for the unnecessary compliments, Nicole. It’s more than a little difficult to pose for a professional photographer without making a face that falls under the category of “self-satisfied smirk” or “extreme fatuousness.” I hope I was successful. Now, of course, I am serene and unruffled, bursting very nearly at the seams with excellent advice. Onward and upward.

Q. Dumb Emails, Back to Haunt Me: Welcome! I spent the weekend reading some of the stuff you’ve written for the Toast, and wow! Very funny. My question is this: Someone in my office can apparently go through my email and has on occasion found dumb ones I’ve sent. This person prints them out anonymously and leaves them in my mailbox. The most recent one was from a year ago! I know I shouldn’t send dumb emails, and nothing I’ve written is THAT bad. But this feels very creepy, and I’m not sure what to do—I don’t exactly want to talk to my boss about these emails (if she’s not the one printing them out).

A: This is a living modern nightmare, and probably also an episode of Black Mirror. I don’t know exactly what you mean by “dumb,” but it doesn’t sound like you’ve said anything heinous or offensive or that could get you fired. But still! How unsettling and awful. There are a few obvious things you can do to protect yourself—change your email password immediately if you haven’t already, and set up two-step verification so it’s harder for someone else to log in to your account. My apologies if this is something you already do, but make sure you’re completely logged out whenever you leave your computer or go home for the day. If it’s someone who has external access to your inbox—say a higher-up or a member of your IT department—that’s something else entirely.

I understand not wanting to talk to your boss about this, but I don’t think you have much of a choice. Keep the conversation short, explain that someone is printing out your old emails and leaving them for you to find. I would assume your company has a policy against this! Whoever is doing this clearly delights in messing with you and making you feel threatened, and will probably not just quit doing it if you ignore him and hope he goes away. If nothing else, he’s misusing company time. (Also, if you really think your boss is the kind of person who would go into your inbox, print out old emails, and leave them anonymously in your physical mailbox, I hope that you are able to find a new job as soon as possible.)

Q. Ex-Husband’s Will: Many years ago, after our children had graduated university, my then-husband confessed that he no longer wanted to be married to me—he explained that he was looking for excitement and romance, and my plans for retirement (rest, relaxation, and enjoying grandchildren) was not how he wanted to spend his gray years. While I was shocked at first, I accepted his wishes, and we eventually divorced. My ex-husband came from a very wealthy family, and during our marriage he inherited a great deal of money and property. My husband offered half of his ownership in his properties as well as very generous monthly alimony payments, saying that I was entitled to them as his wife for more than 30 years. I had no need for these properties and alimony, since I had saved so much, so I turned down his offer. My ex-husband and I remained good friends.

A few years after our divorce, my ex began seeing another woman, whom he lived with for more than 10 years. I remarried, but a couple 
of years ago my ex-husband became terminally ill, and my now-husband and I assisted with his care, particularly after he and his live-in partner broke up. Before my ex-husband passed away, he admitted that he regretted his decision to divorce me, and that he now felt it was far better to spend your life with your best friend rather than a lover. After my ex-husband passed away, I found out that he had left half of his estate to my husband and me, and the other half to our children and grandchildren. After reading a letter explaining why—that my ex-husband knew I would donate most of it to my preferred social justice projects, while setting aside a portion for our grandchildren—I was touched. However, there is something that has been bothering me about his will: He left nothing for the woman he spent more than 10 years with. I also found out from my former sister-in-law that during their relationship he had his ex-girlfriend sign a prenuptial agreement that she never contested, under which she was to receive a pitifully small amount of alimony for one year after the termination of their relationship and had absolutely no co-ownership of any of his properties. I know that she and her children (from a previous marriage) were heavily reliant upon my husband’s wealth during their relationship. He was paying for her children’s education, as well as her parents’ medical costs. I hear through the grapevine that she and her family have fallen on hard times. I feel awful about this situation. Prudie, my ex-husband was not a vindictive man, but I cannot understand why he left this woman in the lurch.

My children and former in-laws will not discuss with me why my husband did this—they will only say that they are in complete agreement with his decisions regarding his estate. However, I feel morally obligated to help the woman who spent so many years helping to care for my ex-husband. Would it be wrong if I took a portion of the inheritance we received (for example, a property she could either live in or sell) and give it to her? Or should I respect the wishes of my ex-husband?

A: I can see why your ex-husband left his money to you. What a remarkable opportunity for you to do some good! It’s your money to do with as you see fit, and since you’re already living comfortably, I can’t think of a reason why you shouldn’t help out your ex’s ex if you want to. You may have to consult a lawyer for the most expedient way to help her (you don’t want to end up burdening her with a remote vacation home that would overwhelm her in property taxes and be difficult to sell), but offering her a property to either use or sell sounds like a wonderful idea, and one that doesn’t keep you two financially entangled. She can take the money from the sale and do with it as she likes, which would be easier on the both of you than offering to take on her parents’ medical expenses or her monthly bills.

Who knows why your ex-husband decided to cut his girlfriend out of his will. There’s not much point in wondering about it now, and his relatives don’t seem interested in speculating about his state of mind or the state of their relationship. The important thing is that you’re in a position to help this woman and willing to do so. You don’t owe anyone else an explanation for how you decide to use your inheritance. Your ex-husband’s wishes were for you and your children to inherit his wealth. You’re not dishonoring him by being open-handed with what you’ve received, and it’s not wrong to want to help out a woman who’s struggling to make ends meet. Think of this as extending his generosity, rather than contradicting it.

Q. Welcome!: Burning questions of the day have to be: What kind of dog? What kind of cat? Names? Suspect we’ll all be commiserating with you over the next few years as they go through the inevitable golden years/sailing off into the sunset …

A: The dog (a spaniel) is Murphy, the cat (a jerk) is Milo, and neither of them will ever die. They will be the first household pets to achieve immortality. 

Q. Re: Giving Your Daughter a Boy’s Name: We gave our daughter a perfectly acceptable boy’s name. We mostly didn’t tell people until she was born. Stop telling people. They won’t say mean things once she is around. I once commented on the Internet as to my daughter’s name, and I got a flood of nasty, awful things said; so I stopped sharing such things on the Internet.

A: “Stop sharing things on the Internet” is almost always good advice, and refusing to tell people your daughter’s name is definitely one way to keep the pointed questions to a minimum. I’ve seen a few other comments to the same effect. 

Q. Toddler Impressionist: I have a 3½-year-old with an odd fascination with accents. When he hears a new accent, he always wants to know where it is from, or conversely when he hears of a new place, he wants to know the characteristic accent. He likes to try to imitate them. So far, so good. However, in public, he has no compunction about asking people about their accents, guessing where they are from, or even showing off his imitations. Some people on the receiving end find it charming, but others I sense bristle, in that way that anything these days that touches on race or ethnicity risks provoking neuralgia. Is my son’s behavior in fact rude? Or should people just lighten up? And, in case someone is rubbed the wrong way, can you think of a good thing to say to smooth it over?

A: Toddlers are sometimes rude without meaning to be. That is the Deal with toddlers, and why they are given limited responsibilities in our society. It’s completely normal for a 3-year-old to be fascinated with how different people sound (I assume! I have no toddlers). You can answer his questions frankly, encourage his curiosity about the world around him, and gently remind him that it’s not polite to imitate other people to their faces (which is a good life lesson regardless of accent). 

Q. Re: Ex-Husband’s Will: The writer definitely needs to consult a lawyer and a CPA before doing anything. Depending on how much money she’s wanting to give, there could be serious tax implications, not only for the girlfriend, but also for the inheritor herself.

A: Good point!

Q. Re: Dumb Emails: Yikes! This is definitely a security issue. No one except IT should be able to just sneak into your account—what if they were to find out sensitive client information? Work with your IT folks to get your machine and your account secure, immediately!

A: Yes! If this person is willing to print out someone else’s old, embarrassing emails, it’s not much of a stretch to assume that they might be willing to play fast and loose with sensitive company information. They might also have more than one victim. Definitely worth involving your boss, IT, and HR, if your company has an HR department.

Q. Re: Toddler Impressionist: It could be worse. I am told that when I was that age I walked through a train car full of people and asked every single one of them if he or she had a penis.

A: Life is such a rich tapestry.

Q.  Unbalanced Friendship: I have a workout partner—who I consider to be a friend—although that friendship does not extend outside the gym. Whereas I have a small circle of my own friends, my workout buddy “Jim” has only me. This I can chalk up to a multitude of reasons, not the least of which is him simply being an aggressive, judgmental, self-sabotaging, angry individual. I feel that I only continue to put myself through the stress of this relationship because he truly has no one else in his life—and he definitely needs a sane, calm, rational influence. The problem is he gets hurt and offended that I don’t seem as “invested” or share as many personal details of my life as he does with me. But it’s because he makes me uncomfortable, and he’s not someone I would trust with certain aspects of my life. I feel that since I’m his “best friend” he expects to be mine as well—and that’s simply not the case. We work out well together, but I don’t know if this friendship will work out. Does a successful friendship require pure equality between two people? Or is there some way to make this work?

A: I don’t know if a successful friendship requires total equality, but it does require, at the bare minimum, a mutual enjoyment of each other’s company. Staying in contact with someone you actively fear and dislike because you’re worried he’ll do something dangerous without your influence is less of a friendship and more of a hostage situation. It’s completely up to you how much time you spend with him. If you find you can work out well together and set reasonable boundaries with him outside of the gym without too much stress, that’s great. But if he’s constantly demanding more of your time and trust, you don’t have to become his keeper out of a misplaced sense of guilt.

Q. Re: Dumb Emails: It sounds more likely that this person may be printing out allegedly dumb emails sent to a group of people of which he or she was a direct recipient (or got a forwarded copy). The person then printed out a copy of the message (without any identifying recipient’s name). Still inappropriate, but not necessarily an invasion of privacy or IT security.

A: That’s possible, although it’s not clear from the original letter whether he or she thinks that’s the case. What’s oddest about the situation to me is that the emails in question are from more than a year ago. If nothing else, it’s a very odd way to try to alert someone that he or she is forwarding emails too casually and thoughtlessly.

Click here to read Part 2 of this week’s chat.