‘He Heard From His Ex. Now We’re Both Confused.’

Dear Sara: I started dating someone in the beginning of November. Everything was going great, [until] he called to tell me he heard from an ex. [He said it] messed with his head, that possibly down the line we could open back up communication again. I have been continually hurt by men, and I started dating him because he was the opposite of what I normally go for and he made me laugh. After his comment about possibly texting one day, I just hung up, later sending a message that I was blindsided … (more…)


‘I’m Afraid to Get Back Out There’

Dear Sara: I have been divorced for a little over 6 years now. My daughter wants me to start dating again, which I’m very fearful of doing. I have had a few relationships since my divorce, but the last relationship left me broken and fearful of ever getting back out in the dating world again.

My relationship with this guy was on-again off-again. I fell pretty hard for him, and to be honest it was a horrible relationship. I was alienated from my family and friends, which you could say I allowed to happen only because I was so deeply in love that I couldn’t see past him. (more…)

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‘Should I Try to Get Him Back?’

Dear Sara: About a month ago, my boyfriend of two years broke up with me (I’m 30 and he is 31). It came as a heartbreaking surprise. I’ve been in several serious relationships, and this one seemed like a wonderful fit—loving, easy, drama-free. He took most of the steps to advance the relationship in the first year or so, and we had continued to deepen our bond since then.  

He couldn’t really give a satisfying explanation for ending things, and seemed confused himself. We were living in a temporary apartment together (he recently moved to my city after finishing grad school) and were about to get a more permanent place, but he said that [he] was having doubts about the city we live in, the job he has, or what kind of lifestyle he wants, and that he needed some time on his own (single) to figure things out—which I suppose means he had doubts about the relationship, too. He’s also going to start therapy to try to work through some of these issues.


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‘How Do I Re-Enter the Dating World?’

Dear Sara: I just read your article about conquering the fear of rejection and continuing to put oneself out there. My question: How do I know whether my status is a stigma against putting myself ‘out there’? Why is a female widow viewed as unavailable?

I am a widow, and almost every [time] I get into a conversation with a man, I get asked the question, why haven’t I found someone yet? I try to carefully explain that it has taken me time to grieve and to accept going forward with my life after my husband of 29 years passed, but regardless of how politely and positively I explain my past, there is an awkwardness that creeps into the conversation that makes me feel like the man is pulling back, like there are red flags going off. Please advise your thoughts and opinions on how a widow restarts a journey towards a new relationship. — Thank you, P

Dear P: It’s puzzling that the men you’ve met so far want to know why you haven’t found someone yet. Obviously, you did find someone and you clearly were able to have a strong, lasting relationship with him. Far from working against you, it seems to me that should work for you. (more…)


‘I Have No Relationship Experience’

Dear Sara: Growing up, I lived a very sheltered life: Most things were simply given to me, in return for a level of conformity that followed certain expectations. Throughout high school, I was essentially prohibited from being in a relationship (along with strict avoidance of drinking and partying—yeah, those were fun years) as I was led to believe that it would impede on my education and career prospects. I’m 24 now, about to finally graduate with a career in law enforcement just on the horizon, yet another reason why I abstained from a lot when I was younger.

In all that time, I have never been in a committed relationship with someone. I mean, I haven’t even made it to holding hands with a woman. There’s just this deeply ingrained apprehension that prevents me from being romantic, and as hard as I try to “put myself out there,” I feel like they get an easy read on my lack of confidence and inexperience. Now, don’t get me wrong, most of my friends are actually female, but that’s about as far as it ever gets.  (more…)


‘Nice Guys Make Me Want To Run’

Dear Sara: My therapist was telling me that there is a certain pattern in my relationships and that I should rather go for the nice guy to become happy with a man. She tells me that my loving feelings for a man are a sign of “active patterns.” She told me “take the nice guy and you´ll see that after a while you will feel some kind of ‘belonging together,’ and this is what real love is all about.”

If this is what real love is all about, I’d rather remain single! I already tried with nice guys twice in my life. I was rather running away than having feelings of “belonging together.” What do you think? — K

Dear K: I both agree and disagree with your therapist. On one hand, I’m absolutely in favor of choosing nice people to date. Because what’s the alternative: people who aren’t nice? (more…)

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‘I’m Tired of Being Rejected’

Dear Sara: I am a 29-year-old single male with social awkwardness, and I’m depressed because I’m getting nowhere with women. I have met some women online, and I’m lucky to get a second date with just one of them. I take it personally, like it’s me, and have had a psychic tell me it’s because I have bad mantras so I therefore have had a doomed love life. I really want commitment, but want to know what I’m doing wrong. I don’t want any more rejection. I’m sick of being alone and depressed. Help me. — R

Dear R: First, please don’t listen to the words of a self-described psychic who tells you something so mean and disempowering. I can’t believe anyone who truly has spiritual depth or insight would say anything like that.

This psychic sounds like a fraud, and my guess is she perpetuates this particular kind of deception by reaffirming beliefs customers already have. (more…)

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Hey, Let’s Save Democracy: A Plea

Single people often get the message, either directly or indirectly, that their lives are somehow less substantial or more selfish than other people’s. When I was single, this used to bug me, but at a certain point I decided that, rather than arguing, I’d just make sure they were wrong. If I dedicated myself to causes larger than myself, then other people could dismiss me all they liked. I would know the truth.

So I started volunteering. And one of the most fulfilling experiences I ever had happened twelve years ago this weekend, (more…)


When Therapists Date

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…)

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‘My Boyfriend Is Always Busy!’

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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Join the community!

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!



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‘I Don’t Understand Why She Left’

Dear Sara: Two and a half years ago, I met a woman online (I was 43 and she was 33 and an alcoholic, sober for 3 years), and we hit it off right away. She was witty and smart. We communicated really well, and we had great physical chemistry. After a few weeks, she said it was important for me to meet her friends and family so that she could get their opinion of me, so she took me to several events to meet everyone. They all loved me and some commented that they had never seen her so happy. She would say. “This is too good to be true!” She said she had never had a healthy relationship; I told her, “It should be this good in the beginning!”


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‘I Love My Freedom, But I Also Want a Relationship’

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 C: There is a myth in our culture that there are two different kinds of people—those who wish to merge their lives with another’s, and those who wish to be independent and free. While there certainly are people who exist on each end of that spectrum, most of us fall somewhere in the middle. We want a special person to share our life with, and we want to be able to do our own thing. We want someone to talk to, and we want time to think. We want to be able to dash off at a moment’s notice, and we want someone sweet waiting for us at home. (more…)

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Dating With a Disability: ‘Should I Just Give Up?’

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…)

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