Dear Anna,

I've been with my boyfriend for over six years, and I'm exhausted from constantly attending family gatherings and social events alone while he stays home playing video games. Every wedding, birthday party or holiday celebration, I'm the only one without a partner while everyone else shows up as couples. I've started making excuses ...Read more

I often get questions from friends and potential clients alike: “What are your clients like? How old are they? What kinds of things do they ask you?”

Let me let you in…

My client base is about 70% women and 30% men, ranging in age from mid-20s to mid-70s. But most are in their 30s, 40s and 50s. In general, I believe that women are more ...Read more

Dear Anna,

I’ve been with my boyfriend for three years, and I love him—he’s funny, supportive and kind. Right now, we’re living at my sister’s place while saving for our own apartment. He’s 29 and I’m 27. I work full-time as a freelance writer and make a comfortable living, but his part-time retail job barely covers his own ...Read more

While a lot of the advice I give revolves around how to get the first date, even more important is how to nail that first date.

Let’s take a look at some tips for the all-important first date:

What not to do on a first date:

1. Be late without notice

2. Be excessively late, with or without notice

3. Have your phone out or text ...Read more

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 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

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

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

Frustrated with dating apps, singles are are shelling out for high-end matchmaking.

“We had our biggest month of sales in the history of the company last month, and we’ve been around for 15 years,” Adam Cohen-Aslatei, CEO of the matchmaking service Three Day Rule says. “Our business is not shrinking.”

And he’s not alone. Demand ...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.

Question:

I am convinced that online dating is haunted, based upon my ...Read more

Dear Anna,

I'm a 38-year-old gay man living in a midsize city, and I'm completely exhausted by the dating scene here. It feels like every guy I meet on the apps is only interested in hooking up, and when I suggest actually going on a date or getting to know each other first, they either ghost me or tell me I'm "too serious." I've tried being ...Read more