The 22 Advice Columns & Podcasts We're Addicted to in 2019
A big part of the reason Han and Matt "Know It All" is because there are a handful of phenomenally keen personalities in the world of advice-giving who had inspired the podcast (and advice column, Ask a Helping Han) that we used to do (check out Han and Matt Know It All on iTunes).
Click here if you'd prefer to browse this in an index view with a simplified list of columns presented alongside the descriptions, and download our opml file to import the full list of advice columns that Han and Matt follow straight to your Feedly dashboard.
How to Ask: Contact Ask a Manager
Who to Ask: Alison Green
Specialties: Workplace, Career, Boundaries, Discrimination, Interpersonal
One of our Favorites: I Walked in on Employees Having Sex — And I Think There’s a Sex Club in My Office
Why We Read Ask a Manager
Han: Ask a Manager is the perfect mix of entertainment and spot-on career advice. Alison Green's expertise as a hiring manager is a great resource—reading her advice has been an invaluable career tool for me, and I have no qualms counting the time I spend reading this site as "professional development." Come for the no-nonsense career advice, stay for the insanity, however: nothing can make you feel better about the dysfunctions of your own workplace like reading a roundup of the year's worst bosses from AAM! Alison's balance of pragmatism and willingness to express shock and horror when something is far outside of the realm of acceptable makes her required reading for anyone who has a job, full stop.
How to Ask: Contact
Who to Ask: Lindsay King-Miller
Specialties: LGBTQIA, Dating, Coming Out, Sexuality, Relationships
One of our Favorites: How Can You Tell if You’re Not Straight?
Why We Read Ask a Queer Chick
Matt: Like Ask Bear, Ask a Queer Chick has returned to us in late 2017 to become (thankfully!) eligible for this list. In our present dystopian hellscape, Lindsay King-Miller is more valuable than ever and reminds us that the fight for human rights and social justice still needs all hands on deck. A common theme in Lindsay's questions speaks to feelings of not belonging to the queer community—fears of being regarded as fraudulent for taking on queer labels if you've not passed a non-existent litmus test—and she handles this subject matter with such compassion and a resolute principle of inclusivity, her words reaching out to pull the reader into an embrace that says "I see you and I accept you." Lindsay also has a rare distinction among others on this list of having an audience that tends to skew younger, but there's nevertheless an "all ages" application for many of her answers particularly as older generations are only now finally finding the words to describe the feelings (of their sexuality, of their gender) that they've been repressing for decades. Bless Lindsay.
How to Ask: Contact Ask Amy
Who to Ask: Amy Dickinson
One of our Favorites: Co-Worker's Emotional Affair Interferes With Perfect Marriage
Guest Appearance: Hannah and Matt Call Amy Dickinson
Why We Read Ask Amy
Matt: We've been long-time fans of Amy Dickinson, having first discovered her many years ago from listening to NPR's Wait Wait, Don't Tell Me. In particular, her many scandalized interjections which channeled all of us listeners made her a valuable touchstone and voice of sanity for my early appreciation of the show. That incisive wit, expert brevity, and proficiency at getting straight to the disturbing heart of the matters at hand really shines in her advice column in which she shows us each and every day why she's one of the greatest at the advice-giving game.
How to Ask: Contact Ask APW
Who to Ask: Liz Moorhead
One of our Favorites: Am I a Bad Friend If I Can’t Afford a $15,000 Bridesmaid Dress?
Why We Read Ask APW
Han: I started reading A Practical Wedding when I was planning my own wedding back in 2012, but the relationship advice from Ask APW spans the whole range of life, from pre-engagement to post-marriage. Team Practical takes on all the things that we're taught we aren't supposed to talk about: the costs of weddings (and attending them), difficult family dynamics, handling queer identities in a heteronormative social contract, navigating the hard questions that come with a marriage (finances, children, emotional labor), and beyond. They also have a fabulous interactive commenting community who are always willing to share their stories and experiences, their support and advice, and their righteous anger when needed.
How to Ask: Contact
Who to Ask: S. Bear Bergman
One of our Favorites: How Do I Talk to My Partner About Nonmonogamy?
Patreon: Ask Bear
Why We Read Ask Bear
Matt: Ask Bear is back after a long hiatus! A self-described fellow 'busybody know-it-all,' Bergman puts his awesome power to use not only with thoughtful essays tackling complex questions around gender identity and sexuality, but he also has been known to volunteer his time on Yik Yak to answer questions for teens and young twenty somethings who may otherwise be in dangerous LGBTQIA-phobic environments. Ask Bear is doing tremendously important work destigmatizing and supporting the queer community and their experiences—and advice-giving is just one slice of that activist pie. Check out S. Bear Bergman's homepage to learn about their multiple efforts in support of the community.
How to Ask: Contact
Who to Ask: Harris O'Malley
One of our Favorites: My Girlfriend Wants To Try Sex With Another Woman
Guest Appearance(s): Hannah and Matt Romance Dr. NerdLove
Why We Read Ask Dr. NerdLove
Matt: As a longtime nerd / man / reader of Kotaku, Ask Dr. NerdLove has long been on my radar, years and years before my obsession with the medium really took flight. That may in fact be part of what makes O'Malley such a rare gem and an irreplaceable fixture in the advice genre; he's been serving a market of readers and listeners who—demographically speaking—are often the source of letter writers' woes rather than the ones asking the questions and typically seek out advice columns in much smaller numbers than their AFAB counterparts. In spite of (or perhaps because of) that, O'Malley navigates questions From the Other Side with a determined empathy to often express, in effect, "As a man, I used to believe this very shitty thing, too, so I get it—but cut it out." That's the flip side of O'Malley's advice: some question askers require very tough love, and Ask Dr. NerdLove is a masterful dispenser of tough-but-vital pills to swallow. The cherry on top of this pill cocktail is that O'Malley goes the extra mile with occasional deep dive "post mortems" featuring a kind of real-time reaction approach to some of the more over-the-top scenarios. See this instant-classic, for example: "Post Mortem: Why Do Women Have All The Advantages In Dating?"
How to Ask: Ask Gigi, DSM
Who to Ask: Gigi Engle, Mike Fishbein
One of our Favorites: Why Don't Women Ever Want To Date Nice Guys?
Guest Appearance: Hannah and Matt Flirt With Guests
Why We Read Ask Gigi & Dirty Sexy Monogamy
Matt: While some advice columnists labor to exclude personal details and anecdotes to instead be the pointedly objective every(wo)man, Gigi Engle does not shy away from taking on the role of the concerned auntie who knows a thing or two that you are absolutely going to be hearing about—sexy and unflattering details and all. Her candor plays especially well in audio form, and the unfettered intimacy and sex-positivity that has come to define Engle's brand is a framework that Han and I both strongly appreciate and aspire to. Update: Although 'Dirty Sexy Monogamy' is no longer with us, I still hold a fondness for it and will keep it on this 2017 list for pod-sterity (credit to "Random Fan-Person" for the pun!). Engle nevertheless can be found all over the internet wherever sex education is needed (it's needed everywhere).
How to Ask: Contact Asking for a Friend
Who to Ask: Liza Featherstone
One of our Favorites: How Do I Stop Harassment Without Involving the Police in a Gentrifying Neighborhood?
Guest Appearance: Hannah and Matt Befriend Liza Featherstone
Why We Read Asking for a Friend
Matt: Growing up, you were probably taught that it was impolite to talk to others about certain topics: salaries, sex, religion—politics. 'Politeness' be damned, Liza Featherstone consistently has some of my favorite questions each week, and much of that is owed to her taking on some of the more extremely-complicated-but-very-relatable troubles that arise from having stark political differences with those in your life whom you may have no means of escape. Her outstanding grasp of intersectionality is on full display, making her one of my favorite writers on the internet period.
How to Ask: Contact Ask Polly
Who to Ask: Heather Havrilesky
One of our Favorites: What Does Love Feel Like?
Guest Appearance: Hannah and Matt Relay Ask Polly
Why We Read Ask Polly
Matt: Heather Havrilesky is expertly sincere in a way that invites you into an intimate embrace with her every sentence, which reveal so much personal anguish and triumph. She possesses a few other notable distinctions, including 1) having the longest written answers of anyone else on this list on average, a testament to her passionate drive to leave no dark corner unexplored in tackling very emotionally complex interpersonal issues, and 2) being a loyal envoy of the word "fuck." Indeed, Havrilesky has many fucks to give, and we should all count ourselves very luck for this bountiful fuck harvest.
How to Ask: Contact Captain Awkward
Who to Ask: Jennifer Peepas
One of our Favorites: Weak Female Lead
Why We Read Captain Awkward
Han: Oh, Captain Awkward. You are the sweet, understanding slightly older cousin with better social skills and endless patience that every weird kid could have used growing up. Jennifer takes on the questions of folks who are questioning themselves, their worlds, and their relationships with tact and love. While she will occasionally let someone know that they're being a complete idiot, she will still rein in the comments sections when they bandwagon on someone too heavily. This site will lead you to some of the weirder questions on the internet—and some of the most nonjudgmental answers that the askers could have hoped for. Funny, compassionate, and endlessly knowledgable, Captain Awkward is always a good read.
How to Ask: Contact Carolyn Hax
Who to Ask: Carolyn Hax
One of our Favorites: When to Start Talking to Our Sons About Rape and Consent
Why We Read Carolyn Hax
Matt: There is at least one very good reason why Hax's innumerable columns produce hundreds upon hundreds of comments and why her weekly chat sessions are brimming with dedicated fans: Hax has been in the advice game for over 20 years, so she's lapped other Malcolm Gladwell acolytes and could in fact be the greatest advice columnist of them all. The sheer volume of questions she covers and has covered—and the consistently unique yet somehow widely relatable nature of those questions—is staggering, and her answers are so concise and enviably astute. As an added bonus, her columns are paired with ex-husband and “relationship cartoonist” Nick Galifianakis's delightfully perceptive comics. There's so much to be in love with here.
How to Ask: Contact
Who to Ask: Courtney C.W. Guerra
Book(s): Is This Working?
One of our Favorites: How Do I Respect My Coworker’s Gender (and My Own)?
Why We Read Dear Businesslady
Han: We're such Ask A Manager devotees that it's hard to believe there would be space in our hearts for more than one job-themed advice columnist. Dear Businesslady, however, is career advice of a different flavor. Courtney Guerra, who wrote for the sadly shuttered The Toast before her monthly(ish) column at The Billfold, composes thoughtful personal essays around some of the timeless questions of working people everywhere - from how to change careers to how to start one in the first place—as well as dipping in to more cutting edge topics such as how to handle transitioning gender identities in a hostile workplace. We love her deep dives and her empathy, and highly recommend adding her to your reading rotation!
How to Ask: Contact
Who to Ask: Raechel Anne Jolie
One of our Favorites: Straight-Passing Queer Blues
Why We Read Dear Comrade Femme
Matt: At the intersectional feminist heart of Dear Comrade Femme is the one-of-a-kind Raechel Anne Jolie, creating something akin to poetry. After I've read Raechel's words, I feel uplifted. Inspired. Loved. Seen. I feel immense gratitude for the beautiful essays that Raechel pens in response to challenging questions from an audience I'm very much a part of who needs the care and nuance of a professor, a feminist, a yogi, a cat mom—a wonderful human whose every word and deed is in the service of making the world a better place. Despite the complexities inherent in the subject matter, Raechel includes citations and links to define many of the ideas that are otherwise commonplace in feminist discourse, making her column as much of a comfort read for like-minded readers as it is a spectacular resource for newcomers. Therefore, I'd recommend Dear Comrade Femme to... anyone and everyone.
How to Ask: Contact
Who to Ask: Kiki
One of our Favorites: Two Is a Couple, Three Is a Crowd
Why We Read Dear Kiki
Matt: Dear Kiki can accurately be described as a hidden gem; this advice column (found only in Iowa City's local magazine Little Village Mag) was completely unknown to me until a listener requested that we discuss the hilarious and disturbing 'I Can't Get My Mind Off of the Speaker of the House,' and I've been hooked ever since. Updates are regrettably sparse, however, and limited to monthly magazine releases, which simply is not enough Kiki. A big part of her appeal to me is that she suffers no fools as she deftly deconstructs fascinating relationship and sex quandaries and delivers some memorable, geeky one-liners like the following: "The thing is, you can do whatever your kinky minds dream of, but with great sex comes great responsibility." Every "little village" deserves a village agony aunt as willing to delve into the tangled mess of modern relationship troubles as Kiki.
How to Ask: Contact Dear Prudence
Who to Ask: Daniel Mallory Ortberg
One of our Favorites: My Boyfriend Has a Tattoo Rating Every Woman He’s Slept With
Why We Read Dear Prudence
Han: Dear Prudence has been a weekly read for me for years and years, long before Daniel Mallory Ortberg took over. However, Daniel's ascension to the throne has been an endless delight. The questions you will encounter here tend to be fairly run of the mill in general, but Daniel's charm, quirk, wordplay, and open-mindedness are delightful and refreshing. Though I don't always agree with the advice, I always agree with the manner in which it is related, with that distinctly "Ortberg" voice that so many of us came to love at The Toast, his previous web project. While I deeply miss the ladies who brunch and the sardonically put-upon women in art historical paintings, I am glad that I still have somewhere to absorb phrases like "Schrödinger's Lesbian."
Who to Ask: Kristin
One of our Favorites: My Mom Says I'm Not Gay. Is She Right?
Why We Read Kristin Russo
Han: I discovered Kristin through the Buffy fan podcast "Buffering the Vampire Slayer," which she hosts with her wife, Jenny Owen Youngs. However, her work on Everyone Is Gay and My Kid Is Gay (which are host to many other fantastic advice givers) is what earns her a place on this list! Kristin's advice for LGBTQ young people and their families is common sense, sympathetic, and sorely needed.
How to Ask: Contact Miss Conduct
Who to Ask: Robin Abrahams
One of our Favorites: Help! A Bernie Bro is Invading My Facebook Wall!
Why We Read Miss Conduct
Matt: Robin Abrahams has a PhD in Psychology and she's not afraid to use it. Where she shines brightest among the advice giver stars is with her patient considerations of the multiple conflicting points of views of the question askers and the subjects of those askers. But no one could be a celebrated veteran in the advice column world with thoughtful psych evaluations alone, and it's those moments when Abrahams lowers her proverbial glasses and drops a deadpan zinger (and a series of very politely-worded insults) that make her entertaining as well as helpful and live up to her column's namesake.
How to Ask: Contact My Brother, My Brother and Me
Who to Ask: Justin McElroy, Travis McElroy, Griffin McElroy
One of our Favorites: The Anxiety-Free Cruise
Why We Listen To My Brother, My Brother and Me
Matt: "The McElroy brothers are not experts, and their advice should never be followed." This is the paradoxical warning preceding every episode of the MBMBaM podcast. So what makes someone an advice-giving expert, anyway, if not producing hundreds of advice-giving episodes (however goofy) and landing a TV show? The brothers may not have crafted their resumes to tell the story of "Professional Advice Givers," but they've absolutely labored to be better, more understanding, more loving, more hilarious, more inclusive, more "yes"-to-everything human beings in a way that they lead their enormous fan base by laudable example. I love these sweet sweet boys and everything that they touch. (Note: the MBMBaM show had previously been on Seeso, a site that has since joined the content marketing platform graveyard. RIP.)
How to Ask: Post on r/relationships
Who to Ask: Redditors
Why We Read r/relationships
Matt: Reddit's Relationships forum has two very distinct advantages to your traditional advice column: 1) Anyone can play the role of advice giver, and those answers are voted on and the best advice can rise to the top, and 2) the question asker can interact with the question answerers, providing additional details and even updates on developments in the story, so there's typically less ambiguity or misinterpretations. Another distinction is that the demographic range covers so many unique groups of people and a wider range of relationship topics than what you'd likely see one advice columnist cover. This is one of my personal favorite sources.
How to Ask: Contact Social Q's
Who to Ask: Philip Galanes
One of our Favorites: Why Can’t My BFF and My New Boyfriend Get Along?
Why We Read Social Q'S
Matt: In my experience, the most common flavor of advice question boils down to this: "I already know what I'm supposed to do, but is there a way I can do this less awkwardly, maybe?" To that end, Philip Galanes's niche of 'lighthearted advice about awkward social situations' in fact gets to the heart of nearly all advice questions in an attempt to diffuse the awkward; the many situations he tackles are ones that I may not have precisely found myself in yet but am likely to, and reading Social Q's makes me feel like I have hundreds of special-occasion aces hidden up my sleeve for whatever may arise.
How to Ask: Contact
Who to Ask: Urban Diplomat
One of our Favorites: Is It Wrong to Invest in Environmentally Questionable Companies?
Why We Read Urban Diplomat
Matt: As its name would imply, Urban Diplomat specializes in matters that are instantly recognizable to anyone with obnoxious(ly close) neighbors, commuter headaches, multi-cultural clashes, workplaces whose proudest feature is their kegerator, and all of the inevitable drama that comes from depending upon roommates because your Rent Is Too Damn High™. If not for the occasional moments of Canadian parlance, I'd be convinced that Urban Diplomat is a neighbor riding the same subway train with me every morning for all of the column's NYC parallels. But I recommend Urban Diplomat not only to big city dwellers to nod along to but to anyone looking for concise, consistently astute answers to many modern day quandaries and nuggets like this: "Friends don’t let friends get fed by the trolls."
How to Ask: Contact
Who to Ask: Autostraddle Team
One of our Favorites: Being Ghosted Says More About the Ghoster and Less About the Ghostee, So
Why We Read Y'all Need Help
Matt: Most online advice columns fit comfortably into a standard blog format. Y'all Need Help, on the other hand, does not like to be put into a box (thank you very much). On occasion, you may get your responses entirely in Instagram Stories chock full of stickers and emoji. On other occasions, personal photographs with silly contextual text overlaid on top of them are interspersed among the advice given. The more playful tone of Y'all Need Help perfectly suits Auto Straddle, and you should definitely be reading the other posts tagged "advice" to be both spectacularly informed and entertained (starting with the essential guide to life: Everybody Publicly and Shamelessly Flirt With Each Other Right Now).
But don't just take our word for it; others have done a great job of shining a well-deserved spotlight on the above advice columnists and beyond, including those from yesteryear. Here are a few we'd like to shout out:
5 Internet Advice Columnists Who Give Better Advice Than Your Mother by Crissonna Tennison
The New Generation Of Agony Aunts Transforming The Advice Column by Claire Fallon
Mallory Ortberg’s Favorite Advice Columns by Mallory Ortberg
The 10 Best Advice Columns Online Today by Rachel Rayner
The 5 Best Female Advice Columnists on the Internet by Kait Fowlie
In closing, here's Heather Havrilesky auguring what would become the inevitable advice column about advice columns just to keep them all straight: