5 Best Free Online Advice Columns to Get Help From Experts

The internet has an opinion about everything. But there’s no reason to rely on random strangers to weigh in with their two cents when there are reputed advice columns to get free help from the experts.

Agony aunts and advice writers are some of the oldest columns in publishing. But several famous advice columns are now behind paywalls, like Carolyn Hax of The Washington Post or Philip Galanes of the New York Times. Don’t worry; there are several free advice columns where anyone can seek help for relationships, work life, mental health, or anything else.

1. Dear Prudence (Web): The Internet’s Favorite Advice Column for Social Questions

  • Who Gives the Advice: Jenée Desmond-Harris
  • Frequency of Posts: Daily
  • Topics of Advice: Relationships, Social Interactions, Life
  • Where to Ask for Advice:Ask Prudie

Dear Prudence is one of the oldest and most popular advice columns on the internet. Started by the online magazine Slate back in 1997, there have been different editors writing the column, but they have maintained the same style of witty, helpful, and centered advice.

Dear Prudence generally targets issues around relationships and people, dispensing advice on how to be socially prudent. Do note that the column has been criticized for its left-leaning advice (but that’s a given considering Slate’s political stance) as well as for featuring fake letters (which several long-running advice columns are guilty of).

There are a few articles restricted behind Slate Plus for premium members, but the regular daily column is still free to read. Each article has multiple questions and answers, and it’s free to write in. Every Monday, Dear Prudence also hosts a live chat with readers, but questions have to be submitted beforehand for that.

2. Ask Amy (Web): Widely Syndicated Daily Advice Column

  • Who Gives the Advice: Amy Dickinson
  • Frequency of Posts: Daily
  • Topics of Advice: Everything Personal and Professional
  • Where to Ask for Advice: Email Amy Dickinson or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068

The Chicago Tribune has been running the Ask Amy advice column since 2003, and it’s nationally syndicated in several newspapers. Online, you can read the column for free on the Chicago Tribune’s website, as well as a few other news portals. You must sign up for a free account on most newspaper sites to read older archived posts.

Generally, Dickinson is warm and kind in her advice, but she is also known for her wit and sarcasm, especially when calling out advice-seekers who are clearly in the wrong. Readers note that she has an innate ability to cut through the clutter and get to the heart of the matter, and then give practical and actionable counsel. She is a font of no-nonsense life advice.

3. Ask a Manager (Web): Best Advice Column for Career and Work Advice

  • Who Gives the Advice: Alison Green
  • Frequency of Posts: Multiple Times Daily
  • Topics of Advice: Work Situations and Career Advice
  • Where to Ask for Advice: Email Alison Green

Ask a Manager is one of the best websites for career advice, helmed by experienced management consultant Alison Green. The questions can be from managers and employees about topics such as career advancement, uncooperative coworkers, and dealing with uncomfortable situations at work.

Alison’s advice has been hailed as being sound and realistic by recruiters, managers, and executives across the internet. Ask a Manager also has frequent update posts from advice-seekers, which makes reading particularly fun. Alison also has a collection of her favorite posts, which is a great place to start reading the column.

Alison answers multiple questions daily (all published on her own website) so there’s a good chance of getting a response. She notes that it’s best to try to keep your emails under 600 words.

4. Dr. Nerdlove (Web): Dating and Relationship Advice for Geeks

  • Who Gives the Advice: Harris O’Malley
  • Frequency of Posts: Thrice Weekly
  • Topics of Advice: Dating and Relationships for Geeks
  • Where to Ask for Advice: Ask Dr. Nerdlove

Dating coach Harris O’Malley’s column Dr. Nerdlove went viral when it was published on Kotaku, targeting geeks who struggle with their love life. Unlike several columns, the questions and the answers are both long and detailed, giving advice-seekers the space to lay out their problem clearly, so that the answer can be as nuanced.

The main page has featured posts as well as the most popular articles on the site, which is a good place to start reading. In the sidebar, you’ll also find a way to filter posts by categories like online dating, what not to do, friend zone, etc. You can otherwise head to the advice column and read articles chronologically.

While most of the questions are asked by men, O’Malley does have women geeks writing in for advice often. The column has been criticized both for being chauvinistic as well as too feminist-friendly, which could be interpreted as a sign of someone who doesn’t lean heavily towards any particular ideology.

5. Captain Awkward (Web): The Internet’s Friendliest and Safest Place to Ask for Advice

  • Who Gives the Advice: Jennifer Peepas
  • Frequency of Posts: No Particular Schedule
  • Topics of Advice: Relationships, Communication, Social Interactions
  • Where to Ask for Advice: Ask Captain Awkward

Captain Awkward is jokingly known on the internet as the “patron saint of break-ups,” writing on relationships and communication since 2011. The focus and philosophy of the blog is to be kind and attempt to be a safe space for people troubled by difficult situations.

Peepas is a screenwriter and filmmaker and notes that her expertise is not in the advice itself but instead in helping people frame how they can communicate what they want to say. Her advice style is friendly, practical, lucidly written, and with dollops of humor thrown into every entry.

The column has a large and enthusiastic fan base, who have created forums to discuss Peepas’s articles, glossaries for oft-recurring terms on the site, and even regular meetups. Peepas has created a helpful page for newcomers with her best posts on dating, breakups, friendships, difficult people, and mental health. The tags in the sidebar are also a quick way to find topics you want to read about.

What to Know Before Asking for Advice

Before you start writing in for advice to any of these columnists, you should probably read a few of their posts first. You need to know the philosophy and approach of the advice-giver to figure out who you would take seriously.

Another thing to be aware of is the comments section. People will give feedback, unsolicited or not, and often judge you harshly. It’s pretty much unavoidable. Also, while you might crave anonymity, it’s possible someone will guess your identity even if you mask it with fake names and details.

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