Hi Sara: I am 57, female, in private practice as a therapist. I am having trouble moving from the 2-D world of internet dating to actual dating. Or maybe I am doing OK. I don’t know. I’ve have had about one date a month from internet dating the last four months and realize I am rusty.

I don’t drink, for many reasons. I do believe in God but am open to dating people of varying faiths, and I realize my anxiety is causing me to overshare. Sometimes when I share that I am a therapist men get wigged out too—as if I am telling them they need therapy. I feel like telling men I am a cheerleader, as that primarily describes my job. People tell me I am smart, beautiful and sweet. Recently I got asked out, and I gave my business card as my phone number. No phone call to make plans to go dancing as we discussed in person. Not sure how to be myself and be a little different and still date. — R (more…)

Dear Sara: My boyfriend and I have been dating for 7 months now. I am 52; he is 55. It started very slow, but he makes me feel very relaxed and cared for when we are together. But the problem is, he is so busy with work, sometimes working without any time off for 3 to 4 weeks straight that I hardly see him.

He is a best friend, he loves me—that’s what he said. But he needs to work a lot and long hours. Meanwhile, my schedule is so different from his that it seems like a long-distance relationship, even though we live 20 minutes from each other. I like independence, but the rare dates we get starts to make me feel unhappy.
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Earlier this year, I spoke with a lovely woman who was struggling with the challenge of being a Single Woman of a Certain Age. She was one of dozens of smart, kind, sensitive and utterly sane women I have met since publishing It’s Not You. She was also, like so many other women I have coached, feeling very isolated. The problem wasn’t simply a matter of not having a romantic partner; it was also that she didn’t have close friends in the same situation.

I wanted to find a way for these women to meet each other, so I recently launched at community forum on my web site and it has been off to a great start. Please take a look and consider joining us!

Dear Sara: I’m a 34-old-girl who never had a proper relationship. l started to feel so lonely, and seeing [people] all around me having someone makes me feel bad about myself. On the other hand, I do like my independent and free life but still want someone next to me. I wonder: Do I ask too much or is it because I don’t know what I want, that’s why I don’t get it? I’m so confused and frustrated and on top of that is that every time I like a guy I get overshy and awkward and I end up sounding like a dumb and silly girl—hate that feeling!! What can I do to stop all of that and be more confident? – C

Dear Sara: I’m in Seattle and dating here is brutal. I’m 41, educated, funny, fairly attractive, and kind/courteous. I’m looking for the real thing. Here’s the problem: I was almost killed in a car wreck two years ago and my ankles and feet were crushed, every single bone, as well as others in my legs and arm. I will always walk with at least one forearm cane, and probably will have two. In a culture where texts aren’t returned because of a wrong shade of lipstick, what can I do? (more…)

I’m so happy to announce the publication of the IT’S NOT YOU audiobook. I originally wanted to read the narration myself; fortunately they hired Nina Alvamar instead. She reads the book just as I would–except MUCH better. Here is a sample from Audiobooks.com.

Dear Sara: I’m 49 years old. I’ve never been married, and have no children. I dated a guy for 15 years, thought we would be married and have kids, and we have been broken up for over 10 years. It took me three years to get over that relationship because he immediately found someone 10 years younger, built like a brick house. [He] moved her in, bought her a car, paid her a salary, and got engaged. I immediately started working out, thinking if I could lose weight, he would want me back because he always told me if I would just lose weight, he would marry me.

I have been a successful business owner for almost twenty years and everyone tells me I’m single because I’m intimidating to men because of that. I’ve only dated about four guys over the last 10 years and all but one seems to have used me for money or sex. … (more…)

Dear Sara: A while back, I had a “come to Jesus” moment with a [single] friend/mentor when she was implying, yet again, that marriage is a sign of spiritual maturity. I argued it was luck. I said, “Tell me one thing a happily married woman (I decided to make it easy for her by excluding the unhappily coupled) knows that I don’t.” She said, “She knows how to show up in the world completely as herself.”

This resonated so deeply with me. Not only do I struggle with intimacy/shame/perfectionism issues, so do all my single friends. It made sense to me that in order to be happy in a relationship you have to be courageous enough to show up as yourself. I really appreciated your mentioning how courageous it is to continuously put yourself out there in dating, but for me, that’s social courage; I know how to present myself favorably to a wide variety of people. I think intimacy is a deeper kind of courage. (more…)

I started binge-listening to The Secular Buddhist podcast last year because the host, Ted Meisner, always has such fascinating guests and offers such a smart take on Buddhism in the modern world. So a few months ago, I summoned my nerve and asked Ted if he’d be interested in talking to me about It’s Not You and the way Buddhist teachings helped me deal with the challenges of being single and of dating. I was thrilled when he invited me on the program.

In the conversation, we talk about how I discovered meditation and Buddhist thought, how it has helped me personally, and how I ended up writing an “inspirational book” even though that phrase makes me a little queasy. You can listen here.