Life Advice

Ask Anna: Starting over -- dating with confidence after a long break

Life Advice / Dating Advice / Jul 16, 2025

Dear Anna,

I recently got out of a long-term relationship — seven years, monogamous, talked-about-getting-married serious. I’m 34, and this is the first time I’ve been properly single since my mid-20s. It’s been a mix of freeing and terrifying. The dating scene feels like a completely different planet now — apps, situationships, ...Read more

Millennial Life: The Luck of Not Dying Today

Life Advice / My So-Called Millienial Life / Jul 13, 2025

I don't want to write today. There wasn't much to say after watching the horrors scrolling on my phone. Whatever I could try to shape into language feels inadequate against a video that rewires your nervous system.

It showed women and children waiting in line outside a clinic, and then they weren't. They were bombed. There was a bloody white ...Read more

Single File: Think in Many Tenses

Life Advice / Single File / Jul 09, 2025

It's a complicated challenge, this single life. On your own, shunning both dependency and isolation, you adjust after a while and learn to be in the present moment. Sleepless nights have taught you that you should not voyage into the future (what could be) too often or dwell in the past (what might have been). The fancy footwork needed to ...Read more

Ask Anna: I feel like I'm competing with my boyfriend's hobby for attention

Life Advice / Dating Advice / Jul 09, 2025

Dear Anna,

I’ve been with my partner for two years in a rocky but loving relationship. Our main issue is his all-consuming passion for photography. He's on his camera club's volunteer committee, attends meetings every Monday, shoots Wednesday and Thursday evenings plus some Fridays, and spends Saturday and Sunday mornings on photo walks. He ...Read more

Ask Dating Coach Erika: When should you ask about their financial situation?

Life Advice / Dating Advice / Jul 09, 2025

A question I occasionally get (though, not too often since I mainly work with people in the very early stages of meeting and new relationships) is this: “When should I ask the person I’m dating about their finances?”

This has been especially relevant lately in light of the movie "Materialists" out right now about a matchmaker is ...Read more

Millennial Life: Dear America - There's Still Hope for Us

Life Advice / My So-Called Millienial Life / Jul 06, 2025

Dear America: The Fourth of July was hard this year. The flags still waved, the fireworks still cracked across the sky, but it's an empty celebration when Congress voted for millions to lose health care, when people cheer for humans to be eaten by alligators, and where masked people disappear people off the street, the work site, while gardening...Read more

Olivier Morin/AFP/Getty Images North America/TNS

Ask Anna: My partner uses AI for emotional support instead of me

Life Advice / Dating Advice / Jul 03, 2025

Dear Anna,

I've been with my girlfriend for eight months, and I'm starting to feel like I'm competing with her phone for her attention — but not in the way you'd expect. She's become obsessed with AI chatbots. At first I thought it was just a novelty thing, but now when she's stressed about work, upset with her family, or even excited about ...Read more

Single File: Sexual Bill of Rights

Life Advice / Single File / Jul 02, 2025

Sexual expression is part of mental and physical well-being. On that, we agree. And as a single person, you also know how important it is to feel caring and commitment from a partner. The truth is that sexual union has the potential to be spiritual communion. Only when it joins soul mates can it express that high level of togetherness. It is ...Read more

Ask Dating Coach Erika: Was 'Materialists' accurate?

Life Advice / Dating Advice / Jul 02, 2025

As a professional in the dating industry, I received a lot of questions over the last week or so about what I thought about the new movie "Materialists." IMDB describes the movie as, “A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.” But, I was less interested in the plot of the ...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