Life Advice

Ask Anna: How do I ask out someone without it getting weird?

Life Advice / Dating Advice / Mar 18, 2026

Dear Anna,

I could use your help. I rent a parking space during the workweek from a very charming woman who lives in the building across from my office. A coworker connected us through the doorman when I was looking for a space.

From the first time we spoke, there was a … familiarity. She asked if we’d met before. She’s always been kind ...Read more

Millennial Life: The Philosophy of Hope and Destiny

Life Advice / My So-Called Millienial Life / Mar 15, 2026

I'm the one who ends up getting the emails when no one else answers. This time, it was suckering me into taking a board role because the original email request was responded to by crickets. Of course I'd help.

The woman who had filled the role was winding down, not out of desire, but just from the weight of days that turned into decades. She's ...Read more

Ask Anna: He says it's not cheating -- but he's still on dating apps

Life Advice / Dating Advice / Mar 11, 2026

Dear Anna,

My boyfriend and I have been together for a little over two years. We live together with his two boys and my son. About a year ago, I found out he had been cheating on me. He was messaging women on dating apps and Craigslist, and he was also talking to and possibly hooking up with trans women. I found emails and texts with several ...Read more

Single File: Community as Connection

Life Advice / Single File / Mar 11, 2026

Linking yourself to the community is the next step in widening your circle of connectedness. By joining a voluntary organization or international agency (whichever seems more important to you and seems to need you more), by manning a hotline for a battered women's shelter or by helping to organize an international fast day to raise awareness of ...Read more

Ask Dating Coach Erika: Can I take a break from my relationship?

Life Advice / Dating Advice / Mar 11, 2026

Another day, another set of dating questions. Have any of these been on your mind lately?

Q: Is it OK to ask for/take a break from the relationship I’m in if I am feeling stressed out by it?

A: If your relationship is making you feel stressed out, taking a break will not get to the bottom of it.

This is really where you have to do some ...Read more

Millennial Life: Seeing It All Together

Life Advice / My So-Called Millienial Life / Mar 08, 2026

Something I have lamented as a parent is that the cultural touchstones of episodic television were not something my kids would experience. Streaming changed the rhythm of watching TV, especially when shows arrive all at once and people watch them at different speeds. The sense that millions of people might be sitting down at the same time to ...Read more

Single File: Children as Connection (Part 2)

Life Advice / Single File / Mar 04, 2026

Yes, your children can be a link to life outside parenthood. But how?

--At their religious school, be part of the services. Join the ladies auxiliary. Volunteer to host a meeting of the parents at your home. (Put those singles nights on hold for a while; taking part in your children's lives is much more gratifying.) Your kids will be proud of ...Read more

Ask Dating Coach Erika: How do I heal after a sudden breakup?

Life Advice / Dating Advice / Mar 04, 2026

We have another batch of dating and relationship questions today. Get ready!

Q: How do I heal after a sudden breakup? I feel no desire to ever date again.

A: What you're feeling right now is completely normal. It feels like your heart is literally broken. You feel like you never want to date again. Don't try to override that feeling. It's part...Read more

Ask Anna: She used to have lots of sex -- why not with me?

Life Advice / Dating Advice / Mar 04, 2026

Dear Anna,

My girlfriend and I have been together for a while, and we have a genuinely loving, solid relationship. The one real struggle is our sex life. This isn’t a case of the mythical “lesbian dead bed,” because we’ve never had a lot of sex. From the beginning, she’s had reasons for not being in the mood — weight gain, stress, ...Read more

Millennial Life: Old School Could Be the Future

Life Advice / My So-Called Millienial Life / Mar 01, 2026

One coffee shop has become, through habit, an extension of my office. Today's meeting was with a field representative of a state congressional delegate. He wanted to share opportunities that might be available at a federal level. I spied a name written on the opposite side of the notebook where he was writing and told him I knew that person too,...Read more

Ask Anna: My boyfriend keeps prioritizing other women -- what do I do?

Life Advice / Dating Advice / Feb 25, 2026

Dear Anna,

I’m 32 and my boyfriend of three years constantly prioritizes other women over me in small but consistent ways, and it’s driving me crazy. He’s a generally nice guy — the kind who prides himself on being helpful and chivalrous — but somehow I’m never the one receiving that treatment. A few recent examples: We were at the ...Read more

Single File: Children as Connection (Part 1)

Life Advice / Single File / Feb 25, 2026

Skip today's column if you're looking for startling new techniques guaranteed to benefit the children of mateless mothers like you. As much as I feel a special tenderness for young people who grow up with a single parent (my own son, Scott, was only 4 when he became part of a two-person family), what we're interested in right now is you. ...Read more

Ask Dating Coach Erika: How many dating apps should I be on?

Life Advice / Dating Advice / Feb 25, 2026

We’ve all heard the sayings “less is more” and “quality over quantity,” and in many ways, those phrases apply to the world of online dating, at least in terms of how many dating apps you should use. But with all the platforms available, it’s common for single people to be using more than one app at the same time… in fact, I ...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