Life Advice

Single File: Cohabitation Quiz

Life Advice / Single File / May 14, 2025

Let's take a summer break from the usual, same-old (yawn) essay format and sprinkle some questions about living together as a lifestyle choice and (quite possibly) rebellion against marriage. My nationwide survey saw it coming, this fast-growing option, but no one could have predicted its overwhelming numbers. As it turns out, this extra-legal ...Read more

I'm the only one asking questions!

Life Advice / Dating Advice / May 14, 2025

In online dating, I often see two competing factors:

1. People genuinely want to meet someone great (or at least they think they do).

2. People are lazy and don’t take the time to do online dating well … or at all.

This conversation happened to a client of mine (the woman in this exchange) on Bumble:

Her: Do you still drink iced coffee ...Read more

Ask Anna: My boyfriend just met my ex-hookup -- now he won't talk to me

Life Advice / Dating Advice / May 14, 2025

Dear Anna,

I was 23 when I finally got my own place. There was this attractive guy who lived down the hall from me and we had some flirty exchanges that eventually led to a hookup. Just a one-time thing, and afterward we'd only exchange quick hellos if we ran into each other. A few months later, I met my current boyfriend, who I've been with ...Read more

Millennial Life: From Ghost Stories to Gatekeeping: Millennials and the New Wave of Book Bans

Life Advice / My So-Called Millienial Life / May 11, 2025

Starting at about second grade, when the novelty of reading about a family of bears started to wear off, I inhaled ghost stories. One of my favorites was "Wait Till Helen Comes" by Mary Downing Hahn. It was about dead kids, dead parents, and, the cherry on top of a trauma sundae, navigating a blended family.

I was lucky as a child. I didn't ...Read more

Single File: Chairman of the Board

Life Advice / Single File / May 07, 2025

Agreed, the month of May is the usual time for tributes to moms' indispensable role. But mine is an off-season paean to those women who -- by some inscrutable twist of fate -- find themselves Chairman of the Board, responsible for every decision in their husbandless household. Why now, and why them? Because while motherhood is sacred in America,...Read more

Sarcasm and online dating: A tough pair

Life Advice / Dating Advice / May 07, 2025

We’ve all been there: Someone we don’t know extremely well—maybe a work colleague or friend of a friend—sends a biting text that immediately causes you to raise your eyebrows. You may ask friends, “Hey...what do you think this means?” Internally, you’re debating whether you should ever talk to this person again ... or if it was ...Read more

Ask Anna: Love after baby -- Mother's Day advice for exhausted new parents

Life Advice / Dating Advice / May 06, 2025

Dear Anna,

My husband and I welcomed our beautiful daughter six months ago, and while we're absolutely in love with her, I feel like my husband and I are just ships passing in the night. Between diaper changes, feedings and sleep deprivation, our relationship has taken a backseat. Date nights seem like a distant memory, and when we do have a ...Read more

Single File: What If or As If?

Life Advice / Single File / Apr 30, 2025

Years ago, during my single-mom-and-widow phase, fear was very much the biggest part of my emotional baggage. A whole family of what-ifs would wake me in the middle of the night and start droning their litany of fear. What if my son never again has a father? What if I get sick and can't care for him? What if that nice man I just met doesn't call...Read more

Straight talk on the small (but often stressful) stuff

Life Advice / Dating Advice / Apr 30, 2025

Whether you're navigating first-date logistics or attempting to decide dating app behavior, dating today comes with a thousand tiny decisions that can leave you second-guessing.

I get these kinds of questions all the time, so here’s a roundup of real scenarios — with my unfiltered takes — on how to handle them. Spoiler: None of these ...Read more

Ask Anna: How to tell your spouse you want a divorce without getting pulled back in

Life Advice / Dating Advice / Apr 30, 2025

Dear Anna,

After 12 years of marriage (17 together), I (38F) am ready to end things with my husband (40M). We've had our ups and downs — early struggles when he was unemployed, ongoing imbalance in household responsibilities and communication issues. While I handle most domestic tasks despite earning more, he contributes minimally and seems ...Read more

Ask Amy: Exiting with some well-worn wisdom

Life Advice / Ask Amy / Jun 30, 2024

Dear Readers: Since announcing my departure from writing this syndicated column, I have heard from scores of people across various platforms, thanking me for more than two decades of offering advice and wishing me well in my “retirement.” I am very touched and grateful for this outpouring of support.

The thing is – I don’t think of ...Read more