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Dear Anna,

I’m stuck in an uncomfortable spot between two people I care about, and I don’t know how to handle it without blowing something up.

My partner and my closest friend recently got into a pretty heated argument. It wasn’t about our relationship or someone crossing some huge moral line — it was more a clash of personalities and ...Read more

Q: My extended family always asks me nosy questions around the holiday season. Is there a way I can tell them not to? And if that doesn’t work, what should I say when they ask? I really don’t want to talk about my love life with them. Thanks!

A: I get it. Even if they have the best intentions, it feels so personal, and often invasive, to be...Read more

Dear Anna,

I’m 24 and recently started seeing a guy I’ve had a crush on for six months. We finally went on two dates and both went incredibly well. He was affectionate, introduced me to his friends, cooked me dinner, even cleared a little space on his bathroom shelf for my toothbrush. It all felt very sweet and intentional, and I left his ...Read more

I got this interesting question recently, and it made me think. And when things make me think, you know I have to write about them!

Q: How do I balance ‘You deserve zero red flags’ with the reality that no one is perfect? Thank you!

A: Those are VERY different things. A red flag, by my definition, is objective: Someone is rude to people. ...Read more

Liz Dunnebacke isn’t dying, but for a recent end-of-life care workshop in New Orleans, she pretended to be.

Dunnebacke lay still atop a folding table that was dressed as a bed, complaining that her legs hurt. Registered nurse Ana Kanellos, rolling up two small white towels, demonstrated how to elevate her ankles to ease the pain.

“ Mom�...Read more

MINNEAPOLIS -- Dressed in “Team Lisa” T-shirts, two friends posing as savvy business-minded “Sharks” ran through a tight presentation of why any potential investor in the audience would be smart to date their friend.

“When you invest in Lisa you invest in your own future,” they said, as part of their “Shark Tank”-themed ...Read more

Dear Anna,

I’m 28 and have been seeing a guy around my age for a few months. We clicked fast in conversation — texting every day and even saying good night, sharing long voice notes, that kind of early-stage excitement — but because of work and conflicting schedules, we’ve only managed a handful of actual dates.

Last week was my ...Read more

Today, let’s look at two different questions from two different clients. As always, if one person asks, I can only assume it is applicable to a larger audience.

And, interestingly enough, you’ll see that these questions are applicable to any gender and any age.

Q: I wanted to have a conversation with (him) about his more long-term goals ...Read more

Marriage rates in the United States have plummeted nearly 60% since 1970, hitting historic lows amid rising divorce risks and financial pitfalls. This decline isn’t primarily a gender war but a finance-based crisis: The specter of divorce as a wealth transfer discourages commitment.

Enter China’s bold 2025 divorce law reforms, effective Feb...Read more

Dear Anna,

I’m a 29-year-old guy and I’ve been with my girlfriend for about a year and a half. We’ve always had what I thought was a solid, committed relationship. We live separately but spend most nights together, talk about future plans, the whole thing. I trusted her completely. Last week, while she was showing me something on her ...Read more

Every day, I get the question, from both clients and friends, “Should I pay for the dating apps?” And when they are referring to the apps, they are referring to the ones like Hinge and Bumble where the basic services are free but there are in-app upgrades. (Sites like Match.com and eHarmony require payment in order to communicate with people...Read more

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