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