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    Here's What It's Really Like To Be An Internet Advice Columnist

    Five advice columnists on the letters they'll never forget, whether they give advice to friends/family, how to get them to actually answer your letter, and so much more.

    Who among us doesn't love a good advice column? Each one offers so much: The question itself, which will range from mildly interesting to incredibly relatable to deeply embarrassing to totally banana crackers. The moment when you pause and consider how you'd respond to the LW/OP (letter writer/original poster). Reading the advice and deciding whether or not you agree with it. The second life the post gets in the comments. And then discussing the letter and the advice in group chats and on social media.

    The best modern advice columns are kind, practical, progressive, funny, deeply empathetic, and just righteous enough. They teach all of us — not just the LWs — to do a better job of showing up for each other, and ourselves.

    If you're a fan of advice columns, then you've probably wondered at some point how the advice column sausage gets made. Well, good news: some of the best internet advice columnists — Alison Green of Ask a Manager (who kindly organized this roundtable), Daniel Ortberg of Dear Prudence, Jennifer Peepas of Captain Awkward, Nicole Cliffe of Care and Feeding, Harris O'Malley of Dr. Nerdlove, and Jolie Kerr of Ask a Clean Person — are here to tell you all about it. Read on for their thoughts on fake letters, whether they give advice to friends/family, how to get your letter answered, dog fuckers (and murderers??? I'm so sorry???), and so much more.

    What are the weirdest letters you’ve received?

    Alison/Ask a Manager: One of my favorite weird letters was this one from someone whose co-worker stole his lunch out of the office fridge and ate it. It turned out that my letter writer likes his food really, really spicy, and the lunch thief got sick from how spicy the stolen food was. My letter-writer got accused of trying to intentionally harm him, and HR was being really aggressive with him. Later on, he sent in an update and it turned out that the HR person was having an affair with the guy who stole the lunch, and it all came out in a big wave of drama, and the spicy food lover was vindicated. I had another one from someone whose employee was telling her coworkers that she was casting magical curses on them, and her coworkers were all freaked out. Two of them ended up getting sick right after that, so they were even more concerned. The manager wrote to me asking, how on earth do I handle this?

    Daniel/Dear Prudence: ALISON, I remember that spicy stolen food letter! I think this letter sticks out the most in my memory because we had a (happy!) update — a woman wrote in to ask for help because her boyfriend had stopped buying toilet paper after she’d given him a bidet. Stopped buying it so vehemently that when she asked for a few squares for herself, he offered her a cloth hand towel instead.

    Jennifer/CaptainAwkward: Published? Probably the one from the sexist old guy who was sure all his teenaged employees were secretly fantasizing about him (spoiler: they aren’t) and that everyone who saw them working together was speculating about whether they were involved (spoiler: nope!). Unpublished? A lady forgot her keys or her phone at a friend’s house, so returned 10-15 minutes after she left and found him...involved...with a house pet. She was like “do I have to keep this a secret?” and I was like “you do not have to keep the dogfucker’s secrets” but I also did not want to moderate that comment thread. Now all of you can be haunted as I have been haunted.

    Nicole/Care and Feeding: Oh, gosh, I think a bunch about that Captain Awkward letter! He was so sure that he was in his own little Peyton Place, due entirely to being a real stand-up guy. MY favorite weird question? Definitely the one from the stepmother who thought her grown step kids were silently turning her china figurines slightly out of alignment.

    Jennifer/CaptainAwkward: They were totally fucking with her china cabinet, right? Way to play the long game, stepkids.

    Harris/Dr. NerdLove: Occasionally I’ll get letters from folks who have…idiosyncratic…ideas of how dating and socializing works that occasionally get to the point of being absolutely perpendicular to reality. Like a guy who was more than a little convinced that reading a book in public would result in his getting attacked by roving packs of Twilight-reading jocks that I guess escaped from a screening of Revenge of the Nerds or something.

    Jolie/Ask a Clean Person: The sex questions are always wild. The jizzcliner (yes, a recliner covered in semen) is probably the most infamous of the lot, but I also remember fondly the one from the lady who had really expensive Pratesi sheets that her boyfriend was staining with skidmarks when they were doing the deed. Recently, I got an email that was sent during a bachelor party that involved spray tanner and a drilldo; I had a lot of fun with that one on Twitter and ended up using it for a podcast episode about what to do when you have a cleaning disaster in a rental house or AirBnB.

    Jennifer/CaptainAwkward: Thanks for teaching me what a drilldo was!

    Harris/Dr. NerdLove: And today I have learned something new and terrifying.

    Jolie/Ask a Clean Person: Haha — you are both very welcome! I think people are often surprised at how absolutely WILD cleaning advice can get. I definitely have a great job that never ceases to surprise and delight me, even after all these years.

    Are there any recurring themes in your inbox that surprise you?

    Alison/Ask a Manager: I didn’t originally anticipate how many questions I’d get where the answer would come down to “you need to just talk to the other person and be straightforward.” It applies to so much — from the person who’s annoyed that her coworker is playing music too loudly, to the manager who’s frustrated by an employee’s work habits. But having read thousands of those letters now, I think people do know at some level that the answer is going to be “speak up.” What they’re really asking is, "How do I have this conversation in a way that doesn’t negatively affect the relationship? What does that look like and what does it sound like?"

    Jennifer/Captain Awkward: To build on what Alison said, the “How do I have this difficult conversation with someone without offending them or alienating them (even though there is a laundry list of offensive or problematic stuff they are doing to me)?” is one of the most common questions I get. The other most common question (why I changed my Twitter handle to The Marie Kondo of Breakups) is: “I am really unhappy in my relationship but I do not know how to break up with this person.” We really don’t teach people how to leave each other.

    Daniel/Dear Prudence: Most of the themes I see repeatedly are sad but not surprising — very often, if a family member has been accused of (or oftentimes, even convicted of) assaulting or abusing someone else, the family will close ranks around the abuser. But the one that’s surprised me the most I think is hearing from parents whose grown children are fighting tooth and nail over which sibling is getting the “most” financial assistance when they’ve all already received free rides to college, down payments on their homes, paid-for vacations, and cars. I know on some level that having a great deal of money does not always translate into massive personal happiness, but the idea that someone could receive financial assistance on that scale and still, well into their forties, kick at the idea of another relative getting money in a time of great need is really something else.

    Jennifer/CaptainAwkward: Daniel! The abuse thing is so real! Families really are all about the whole “I know Creepy Uncle did unmentionable things to you as a child, but it’s your wedding, can’t you be the bigger person?” pressure. I really owe the “flames on the side of my face” gif creator some royalties.

    Harris/Dr. NerdLove: On the practical level, a good two-thirds of my job would disappear if people would stop trying to read the tea leaves and either directly ask a person out on a date or tell their partner exactly what they just told me, often the same way they told me.

    Alternately, I get a surprising number of letters about either celebrities or parasocial relationships with YouTube stars, Twitch streamers, cam girls, and so on. Half the time it’s managing dating someone in the public eye, the other half is me trying to explain to someone what a parasocial relationship is and why he doesn’t have a relationship with the cam girl he’s been sending gifts to.

    Jolie/Ask a Clean Person: There's a phenomenon that happens to me from time to time in which, in the span of a few weeks, I'll receive several thematically similar questions for no apparent reason. One time it was gasoline on pants, another time a pound of butter melted into car seats. (I've actually gotten that one *three* times!) It's normal to get similar questions that are pegged to a season, like pine needle cleanup in December, but this is a whole other thing. It's weird and delightful and I have no explanation for it but I hope it never stops happening!

    The other really weird thing that I have no explanation for is why my New York Times readers, in particular, have such a problem cleaning their glass shower doors. The volume of questions from that specific audience is so mind-boggling that I wrote about it in the Smarter Living newsletter...which did nothing to stem the tide of questions.

    Jennifer/CaptainAwkward: I love it when thematically similar questions come in, but it’s always strange when something comes in that I’ve answered many times before (“He does no housework, the sex is bad, you pay for everything, he’s not nice to you, LITERALLY A HOUSEPLANT WOULD GIVE YOU MORE PLEASURE, BREAK UP WITH HIM”). And then I realize, oh, they know their story isn’t different from the others but they want so badly for it to end a different way. And that makes me love them and their obstinate loving hearts, and so I write another breakup manual.

    Harris/Dr. NerdLove: I call those the Sir Mix-A-Lot questions. “Everything’s great, now here comes a huge BUT.” And that “but” is always something or a long string of somethings that invalidates pretty much all of the “good things” that their relationship supposedly has.

    Alison/Ask a Manager: Jolie, didn’t you once tell me that once you started writing for Deadspin and your audience got much more male, you had a dramatic increase in questions about keeping sofas clean? Because men are, apparently, really into their couches? I love that.

    Jolie/Ask a Clean Person: Oh man, the couch thing was so charming! Yeah, the uptick in questions about couch cleaning when I started writing for men was unexpected, but maybe not as unexpected as the fact that, other than that, there really weren't many differences in what men and women were asking about. I loved that! Everyone is gross, hurrah for equality among the sexes.

    Nicole/Care and Feeding: In the parenting advice realm, I’m constantly struck by how every single question is clearly brimming with the asker’s own issues from childhood and their current sense of self. Nothing is casual. There’s seemingly no way to discuss car seat use with your child’s grandparents without tears, because to push back on a dissenting opinion must be the same as rejecting the totality of your ancestors. And I GET IT! Oh, boy, do I get it.

    Have any of you ever gotten the “the problem you think you have is not the problem you actually have” letter?

    Daniel/Dear Prudence: Sometimes, yes. Either it’s because someone is trying very hard to see the best in a person who is treating them very badly — in which case I try to be as gentle as possible, because it can be hard to acknowledge that someone you love is intentionally harming you — and sometimes it’s because someone is acting like a villain in a Reese Witherspoon movie. Those are usually letters where the phrase “you need to radically alter the orientation of your heart” comes up in the reply.

    Nicole/Care and Feeding: All the time. Absolutely. And, sadly, usually in the multigenerational abuse realm. The asked question is “How can I tell my stepdad not to talk about Alex Jones in front of my children?” and the question I need to actually answer is “Is it possible for me to bar my door to a man who physically and emotionally abused me for six years, even if it makes my mother sad?”

    Jennifer/CaptainAwkward: The lengths people will go to minimize the mistreatment they are suffering and pack it all tightly into a side question about the daily commute or how much water to use when cleaning a teapot will never not surprise me, will never not break my heart.

    Harris/Dr. NerdLove: God yes, the people in abusive relationships who haven’t realized that this is not normal, this is not OK are absolutely heart-wrenching.

    I also have an entire subgenre of letters of people who have convinced themselves that all they need to start getting dates are the secret techniques that surely everyone else got growing up, when the real issue is that their attitude (about women, about themselves or both) is horrifying.

    The “It’s not because you’re a nerd, it’s because you’re an asshole” scene in The Social Network is so very, very real.

    Do you ever think a letter might be fake? What do you do when that happens?

    Jennifer/CaptainAwkward: I answered one, once. I treated it like an exercise in empathy. What if we take the people in this story very, very seriously?

    Daniel/Dear Prudence: Every once in a great while, maybe every six months, I’ll get a letter that is very clearly either someone’s sexual fantasy (“I NEVER thought this would happen to me, but my beautiful 19-year-old step-niece, a co-ed, recently invited herself out to my lake house…”) or a thought experiment with a clear axe to grind. I don’t run those. But sure, I get a lot of letters, all of them could be fake! Just last week in the live chat someone asked a question about sibling rivalry and then a commenter said that that was the plot of the show The Venture Bros. Then I got confused for a minute because I had that mixed up with Frisky Dingo, and I have seen Frisky Dingo, and I was pretty sure I’d have recognized the plot of Frisky Dingo if someone had written in about it. I cannot watch every popular TV show, and I cannot fact-check an anonymous letter, so my general approach is that unless something seems super-off, I’ll take it at face value and answer it. Even if those particular brothers are animated, I’ll wager at least one pair of siblings can find something relatable in that situation. And I get paid either way.

    Harris/Dr. NerdLove: I’ve had one letter come in that was an attempt to get me to condemn a victim of GamerGate. That one never got past my inbox. I also had one that was so fantastical and over the top that I questioned whether it was real or not. I answered it anyway, because even if it was fiction, there were enough elements that people could relate to and could use advice on.

    Alison/Ask a Manager: I’ve definitely had some letters where I think “no way is this true.” I don’t run those. (And then I also feel vaguely guilty in case it is true and this person has a terrible problem and I’ve summarily dismissed them.) But I also think people tend to underestimate how much weirdness is really out there. I’m sure I’ve been punked sometimes, though! All advice columnists must be punked now and then, right? Ultimately, though, I don’t worry about it too much; if the answer will be useful to other people, then it’s fine.

    Jolie/Ask a Clean Person: If my fake question spidey sense pings, I'll generally either 1. ignore it, or 2. post a screenshot of the email on Twitter and ask people if they think it's real or fake. That's actually a fun game to play! Twice that I can recall I've run questions that were either clearly fake or…um…questionable. (Sidebar: Both questionable questions involved male genitalia!) In both instances I acknowledged the issues with the questions in my answer and explained why I was using them, like the advice columnist version of showing your math.

    Nicole/Care and Feeding: I got a question I chose not to answer from a mother who claimed to be in a romantic and sexual relationship with her adult son. Was it fake? Maybe! Did I feel that I had constructive advice? I did not. Guys, don’t do that.

    How does being an advice columnist play out in your own life? Does it ever come up in weird ways in your relationships?

    Harris/Dr. NerdLove: I get the relationship equivalent of “does this look infected to you?” at parties when I explain what I do. There’ve also been a few folks I know who’ve written in to the column for advice, occasionally with more detail about their lives than I was ready for. That occasionally makes for some awkward moments afterwards.

    The weirder part for me has been when friends who didn’t know I write my column suddenly find it. And because a lot of my advice comes from my experiences, I’ve had people ask “Wait, is this bit here about me??”

    Jennifer/CaptainAwkward: Sometimes it plays out hilariously, where I’m meeting fans of the blog who expect me to be good and effortless at social interactions, and it’s like “We teach what we need to learn, sorry” so we can end up staring at each other awkwardly for a little while before finally someone talks. My friends and spouse are very supportive, and I probably use them as sounding boards way more than vice versa — “I need mom-friends to weigh in here, is this normal?”

    Daniel/Dear Prudence: None of my friends seem to care much one way or the other. (I have dragged a lot of them on the podcast, though.) Mostly when I meet people and they ask what I do, I say I’m a writer, and the Dear Prudence aspect of my work does not always come up. People generally seem to be mildly interested, but not overwhelmingly so. It’s a fairly low-key aspect of my identity when I’m meeting people socially, I think.

    Alison/Ask a Manager: I sometimes don’t tell people what I do, because everyone has work questions and I don’t always want to spend my massage or dental cleaning answering them. But it’s also an easy way to connect with someone, which is nice. With friends and family, there are times when I’m like “I’m off the clock!” because people think I’ll always be excited to hear their stories about bad bosses.

    The flip side of that, for me at least, is that being an advice columnist can make you fall into advice-giving mode even when it hasn’t been requested. I’m curious to know if the rest of you struggle with that! I sometimes have to be very deliberate about reminding myself, “Hey, this loved one has not actually asked you to try to solve their problem.” That comes up with my husband, mainly.

    Jolie/Ask a Clean Person: I always say I'm like a doctor at cocktail parties, everyone wants to show me their proverbial mole. Except in my case, they want to talk to me about a crazy mess they made, or tell me about their favorite cleaning product or trick, or ask me how to get X stain out of Y thing. I don't actually mind it! I like what I do, and I learn a lot from people who want to gab with me about their cleaning secrets.

    One thing that's a newer issue and is pretty tricky and uncomfortable for me to negotiate is the access that listening to my podcast gives to people I'm dating, because the show is so conversational and I share so much of myself and my life with my listeners. It came up in my most recent relationship — I had to have a "you need to stop listening to old episodes of my podcast, because you're ‘getting to know me’ without me being an active part of it" conversation and everything! So that's kind of weird and I don't really know that there's anything I can do other than manage it when dating someone new.

    Nicole/Care and Feeding: I mostly just get people asking me to ask Danny things on their behalf! I think I get more practical life-coach style questions from people in my life, professional development, etc, and fewer parenting concerns. It’s honestly amazing to me, though, that we have more data points on raising kids now than on essentially anything else that isn’t growing wheat, and we still haven’t figured out what works. Maybe that’s why people don’t ask the question at parties. They know we’re all just throwing mud at the wall to see what sticks, and we still have no idea how best to do it.

    What about imposter syndrome? Do you always feel perfectly qualified to do what you’re doing? Do you ever worry you’re giving the wrong advice?

    Harris/Dr. NerdLove: I deal with imposter syndrome all the time. It’s part of why “Dr. NerdLove is NOT REALLY A DOCTOR” gets repeated over and over again. I’m a loudmouth with a blog; 90% of what I’m trying to do is help people not make the same stupid mistakes I’ve made.

    Jennifer/CaptainAwkward: Oh, hell yes. People are trusting me with their vulnerable stories, and there are stakes to getting it wrong. I try to remind people that advice is just one opinion. If something feels wrong to you, you know your own circumstances best!

    Daniel/Dear Prudence: I tend to think of my perspective as simply one of many. I don’t think people write in thinking that I am an ideal arbiter, or that mine is the last opinion they’ll seek on the subject. I’m less worried about imposter syndrome and more worried about making sure that I’m not playing to an imaginary audience before taking the interests of the advice-seeker to heart – looking to make a joke first, for example, or to “sound deep” or what have you, before I seek to give my best advice on the matter. But I’m not a lawyer, I’m not a doctor, I’m not a social worker or similar sort of professional. My advice is not coming from a place of expertise.

    Alison/Ask a Manager: It’s weird work. I have moments where I’m like “Yes, I have the answer to this problem! I will solve this for you!” and other moments where I’m like “Who on earth am I to wade into this?” And as Jennifer says, the stakes to getting it wrong can be high. I tend to do a lot of caveating — like “if your boss is reasonable, you can say X” or “make sure you adapt this for what you know of your workplace.” But I’d be suspicious of anyone giving advice who felt confident they were right all the time. I think imposter syndrome is a condition of the job.

    Nicole/Care and Feeding: I have the opposite of imposter syndrome. If you offered me an automotive column, I would cheerfully take it, and I didn’t learn to drive until I was 28.

    Alison/Ask a Manager: Ha ha, I was hoping someone would rise to the challenge after I said I’d be suspicious of that. I would read your automotive column, despite having no interest in cars and despite your self-proclaimed lack of expertise. I adore your parenting column and I have no kids.

    How much mail do you get? How do you manage it all? Do you ever send private responses, even when you don’t publish a letter?

    Jennifer/CaptainAwkward: My current backlog is at least 7500+ emails from the last three years that have not become blog posts. I post 10-12 times/month, to give you an idea of proportion. I do sometimes send private responses, but I don’t wanna say that I do or that I will because I don’t want to create the expectation that every single email will be answered or even read. It’s a lot. I can’t wait to see if someone has good strategies for managing their mail. I am a magpie — “ooh, shiny!” — and that’s what gets answered.

    Daniel/Dear Prudence: Oh, gosh. Probably between 40-60 questions a week through the live chat (and that’s filtered/winnowed down by Slate first). Maybe another hundred or two a week through the inbox. Voicemails, too, probably at least a few a week. I almost never send private responses, because if I start doing that, I won’t know when or where to draw the line, and I have other jobs I need to focus on during the week. The good thing about stepping into a pre-existing column is that there were already rules in place — 14 questions for the live chat plus a few live responses, one bonus question for Facebook and another for Slate plus, six questions for the column plus a bonus back-and-forth with Nicole Cliffe for Slate Plus, roughly 5-8 questions per podcast. It’s a fairly efficient system.

    Harris/Dr. NerdLove: I have an absurd backlog spread over both my site and the letters I get for my column at Kotaku, and that’s not counting the people who try to jump the queue by DMing me on Facebook or Instagram. And to be perfectly blunt, a lot of them are variations of questions I’ve answered over and over again and my readers can usually predict what I’d say to them with distressing levels of accuracy.

    I try to keep things manageable by sorting them into “Will definitely answer” vs. “Maybe” folders.

    Jolie/Ask a Clean Person: I'm really diligent about managing my inbox — I read every question when it comes in and immediately file it into my main AaCP folder and, if applicable, into one of the subfolders I have (cars, pets, kids, LAMOB, Braugust, Laundry School, etc.) I try to flag the really good ones but more often than not I just remember they're there and when I'm ready to do a column or podcast episode on a certain topic I'll be like, "Oh yes, go find that Q about the drilldo, that was a fun one!"

    Harris/Dr. NerdLove: Ooh, I like the idea of sorting questions into subfolders by topic! I need to figure out a system for that.

    Jennifer/CaptainAwkward: I even have the folders with categories that a friend created, with great titles like “Can’t Fix Someone Else” or “Roommates” or “Low Intensity,” but the volume is so high I haven’t been good at using them. I need an assistant.

    Alison/Ask a Manager: I have a horrible mail backlog. I get about 60+ questions a day, and I try to at least skim everything new once a day. But I need a better system. I have letters that sit for months before I answer them, and others that I answer the very next day just because the question sparked something for me.

    Nicole/Care and Feeding: NOT NEARLY ENOUGH. I have to steal from the Prudie mailbag! I have also made up two questions from whole cloth. Please send me your questions! I beg you.

    Jennifer/CaptainAwkward: @Nicole: NOTED.

    Are there questions you won’t answer or topics you won’t address? If so, what makes something off-limits for you?

    Jennifer/CaptainAwkward: This is heartbreaking to contemplate, because the mental health and crisis safety net is so very fragile and thin, but I have to sometimes remind people that I am not a crisis hotline. I’m just a lady, and I can’t, like, process your rape with you, or help you get out of your house now if you’re being abused, or talk you through your suicidal episode. I’m not the best person to help you, and also, for my own mental health, I can’t even take that on as a thing I can do. The people writing in are so vulnerable and they definitely deserve all the help in the world! But I’m not set up to give it. On a lighter note, I don’t care if single straight men ever get laid again in this life. Read books by women. Make the world safer for women. Go ask Dr. Nerdlove. Figure it out. Don’t ask me. You will not like my answer.

    Daniel/Dear Prudence: The volume of questions the Dear Prudence inbox gets is such that I couldn’t possibly answer even half of what I get in a week. It’s been around for a pretty long time, and Slate has a pretty big readership, so I’m not really thinking in terms of “What do I want to turn down?” when it comes to the column/live chat/podcast. I tend not to answer questions along the lines of “How do I tell my partner that I want them to lose weight?” But even that’s not a hard and fast rule, if I think the LW could benefit from reconsidering some of the premises of that question.

    Harris/Dr. NerdLove: I’m not going to justify people’s rage at women for not wanting to date them or validate their decision to do something self-destructive or “get back at” someone who theoretically wronged them. I’m always willing to apply the Chair Leg of Truth if a person wants blunt advice as to just where and how they screwed up, but I’m not here to be the guy telling you that you it’s OK to scream at someone who ghosted you, cheated on you or dumped you. It sucks that that happened, my dude, but you’re better off to take the time to heal and move on, not look for ways to get retribution

    Jolie/Ask a Clean Person: I tend to avoid questions that veer more into etiquette/personal relationship territory, like "How do I get my husband to pick up his dirty underpants?" because I don't know your husband and I have no idea what kind of prompting will actually move him to get him to pick up his dirty underpants. Ditto for questions about roommates. I can tell you how to wash dishes, but I don't have much by way of advice for making someone do something they clearly don't want to do or don't think they should have to do.

    Nicole/Care and Feeding: The hardest ones for me is when people are in just horrible crisis, hemmed in by financial strictures, and the answer really needs to be “the world is terrible, I’m so sorry.” Those questions I don’t want to turn into entertainment, and those are people I fold into my prayers at night and try to help offline, and it’s something I sense a lot of us in this job carry in our hearts. The people for whom advice can do nothing.

    Alison/Ask a Manager: I get an uncomfortable number of office bathroom questions, stuff that makes me really squeamish. I have a quota on how many I’ll answer a year. I also tend to avoid answering the ones from parents writing in to try to get advice for their adult children. I don’t know that the kid even wants the advice.

    Nicole/Care and Feeding: I absolutely struggle with the question of trauma. Sometimes there is no way for the letter writer to solve the problem, because the problem is not theirs and they do not have the ability to leave their situation. These are the people I often answer privately.

    Jolie/Ask a Clean Person: Alison, you can send those bathroom Qs to me. I'm happy to take them! It could be like an advice columnist foreign exchange program…

    Alison/Ask a Manager: It’s on. You’re going to regret this.

    If someone wants to write to an advice columnist, are there tips that would help them increase their chances of getting a response (and a useful response)?

    Jennifer/CaptainAwkward: Write a meaningful, descriptive email subject line. I have thousands of emails with the subject line “Question” or “Question for Captain Awkward” that all surely contain important, interesting questions, but when one says “Help me with emotional baggage that is packed in literal boxes” my eye goes right there. Also, learn to love the line break.

    Alison/Ask a Manager: OMG yes, the subject lines. 90% of my inbox has the subject line “Question.”

    Jolie/Ask a Clean Person: Wow I almost NEVER get subject line “Question!” That's too funny, I never really thought about how lucky I am that the queries I get tend to have really descriptive subject lines (a few samples from the past month: "Khakis and Steering Wheels" "Stinking feet sleeping bag" "Red wine puke" "More bleach, new washer, or fleeing the country?")

    The questions that I'm most likely to use in columns or on my show provide detail about the mess in need of cleaning as well as the backstory on how the mess came to be. The human touch — the story behind the mess — is important to me and it's what, I think, makes Ask a Clean Person so good. You can find advice on how to clean up red wine puke in a lot of places, but it's not as easy to find advice columns where people are like, "So hey my boyfriend dumped me and I drank a bottle of red wine while cursing his name and burning his belongings then I puked, how do you get red wine barf out of a white carpet?"

    Harris/Dr. NerdLove: Paragraph breaks. Paragraph breaks, paragraph breaks, paragraph breaks. If my eyes go crossed trying to read a letter, I’m probably going to skip it and pick a different one.

    Jennifer/CaptainAwkward: “Ever since I was a child…” + 5000 more words linking childhood patterns to present-day workplace conflicts = Please go to therapy, bebe. That is what therapy is for. <3

    Harris/Dr. NerdLove: If a columnist has a preferred way to be contacted, please follow that preference. Sending questions to my professional Facebook page (or on occasion my personal one) or other social media accounts isn’t going to get you to the top of the queue.

    Also, I’m not sure if anyone else gets this but putting “please don’t answer this publicly/on your site” in the email tends to mean that the question isn’t going to get answered.

    Nicole/Care and Feeding: Don’t leave out vital information just because you know it will make you look bad. If you say “my husband and I had a huge fight, things were said, there was an incident, and now I cannot be left alone with our child, how do I pursue legal remedies?” I NEED TO KNOW WHAT THE INCIDENT WAS.

    For people who aren't Alison, do you frequently get updates from LWs?

    Harris/Dr. NerdLove: I do on occasion, but never as often as I’d like, especially from folks who’ve written in because they’re in toxic or abusive relationships. But I love, love, love, hearing back from folks and getting updates on how they’re doing.

    Jennifer/CaptainAwkward: Yes! I don’t ask for them, I never want people to feel obligated, but I do love getting them.

    Jolie/Ask a Clean Person: A lot of people give me updates on Twitter about what cleaning products or techniques worked for them, which is so great and very, very helpful for me. Like, they'll ask a question, try what I've suggested and get back to me if it worked or if it didn't work. I generally sign off tweets in which I'm making suggestions by saying "let me know if that works, if not holler and we'll try something else" which I think encourages people to follow up with me.

    Daniel/Dear Prudence: Sometimes! Generally speaking, the people who write in with updates have good news, or at least good news in the sense of “We ended up having to break up, but now I can see it was for the best.”

    Nicole/Care and Feeding: Only once or twice. I assume I’ll hear more when the kids grow up and are either serial killers due to my advice or Supreme Court Justices, or both.

    What question/LWs do you still think and wonder about a lot?

    Harris/Dr. NerdLove: The ones that stick with me tend to be the people on the edge of hopelessness. They’re about to make a bad decision or they feel like they’re stuck in an awful place with no way out. Those are the ones that I want to hear back from the most.

    Daniel/Dear Prudence: The people who have written to me about killing their neighbor’s dogs and are now wondering if they should admit to having done so. I often wonder if they actually do it, and if so what happens next. There have only been a few, I have not heard from many people who have killed their neighbors’ pets. But they stick with you!

    Harris/Dr. NerdLove: That’s the sort of question that would put “ethics of contacting the police” at the top of my Google search list.

    Jolie/Ask a Clean Person: [RAPID BLINKING] DANNY WHAT NOW? You're going to have to tell us a lot more about people writing to you about killing their neighbor's dogs. Under what circumstances are these killings happening?!? Also: I am very glad no one has ever written to me about killing their neighbor's dog, because I would not at all want to be complicit in the cleanup of such an act. (Though: I could help. I WOULD NOT HOWEVER. Team Doggers.)

    Jennifer/CaptainAwkward: La la la I’m going to pretend I didn’t read that about the dogs.

    Alison/Ask a Manager: I think about some of the weirder letters I’ve gotten. I still wonder what happened to the people whose boss was demanding they sign up to donate part of their liver to his brother. And I also worry about people who are in really bad work situations; I had a letter from someone who was being constantly verbally abused by a coworker, and her company knew and just didn’t care. I want her to get out of there and I hope she has.

    Nicole/Care and Feeding: I desperately want to know what happened with this woman who worried her grandsons would stop loving her if they found out she had given a child up for adoption in the Baby Scoop era. She was so wounded and guilty and I wanted to help her so badly.

    Also, I NEED to know how this lady cost her 2-year-old granddaughter not one, but two fingers, and will not sleep until I find out.