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Dear Anna,

I’ve been dating my boyfriend for almost a year, and for the most part, things are great — we’re even talking about moving in together. But recently, during a conversation about past relationships, he admitted he doesn’t find me physically “beautiful.” He said he thinks I’m pretty and loves my personality, intelligence ...Read more

I understand how frustrating dating can feel sometimes, especially when you feel like you’ve been putting yourself out there over and over again. Feelings of frustration are valid.

My first question is this: Are you putting yourself out there in a productive way? Are you on two dating sites? (My recommendation is two, and if that feels ...Read more

Dear Anna,

I've been dating my boyfriend for two months, and while he's incredibly kind and caring, I'm struggling with something that's making me feel insecure. He regularly makes comments like “we should go to the gym together” or “when are you going to start going to the gym?” He works out multiple times a week, follows fitness ...Read more

It happens all the time. You match with someone online. You ask a thoughtful question about their profile, and they respond… with no questions about you back. You try again with a question. They respond with no questions back. Now what?

I want to introduce a concept called 2QS, or Two Questions and a Statement.

Here’s how it works: Give ...Read more

Dear Anna,

I’m a late-bloomer lesbian — came out at 40, two years ago — and was lucky to have a gentle, affirming first relationship that made me feel safe and seen. She was kind and patient, and our physical connection felt beautifully balanced. Recently, though, I dated someone local who was much more experienced and, frankly, kind of ...Read more

As a dating coach, I often get questions about the first date — the length, the venue, the method of parting … you name it. I thought I’d share a few gems this week:

Question: So I've been texting back and forth with this girl for a while now (kept having conflicting schedules), and we're finally getting to meet this Thursday. Can you ...Read more

EMPIRE, Colo. — The Owls were ready to climb after spending a mid-July morning at a small fishing pond in the Rocky Mountains.

“My hands still smell like fish,” one of the Owls — an 11-year-old named Jackson Dana — said. He’d caught two that morning.

Jackson, fitted with a helmet and harness, ran off to the wall, but his twin Kacy ...Read more

Back in 2019 (and for some reason it graced my mind today), the actress Emma Watson brought attention to singledom, not simply by saying that she is happily single but by naming herself as “self-partnered.” It not only acknowledges the fact that being single is a choice, which many people seem to forget, but it’s a valid one at that.

Too ...Read more

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

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