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 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

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