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‘I’m the Last Single One Standing!’

Dear Sara: It happened: The last “single” girl in my friend group got engaged tonight. She and her fiancé had been together for more than two years and live together, so I was expecting it. The other couples in the group all got engaged within the past year (including one ex, for whom I long had unrequited feelings). But now I am truly the only single one left — and do I ever feel like I don’t fit in. I am not dating at the moment — I tried last winter, met a few duds, and decided to take a break since I wasn’t feeling open to it. I would like to be, but I’m just not. Plus, although all of these engaged girls are eager to hear my dating stories, they’ve mostly forgotten how hard it is to be “out there”–or they never really struggled with the dating scene to begin with. I am sad, and I am lonely, and I am tired of first dates. I’d love to be planning my own wedding, but that just makes me sound marriage-obsessed! — E

Dear E: I don’t think you’re marriage-obsessed. I think you’re a human being who wants to spend time with other people who understand you. So that puts you in a pool of about 99 percent of us, I’m guessing. (more…)

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‘I’m Afraid To Get Hurt Again’

Dear Sara: I am scared of dating or trusting a guy again because the last relationship I had almost destroyed me. He broke my heart into pieces. I had never fallen in love like this before. I gave him everything. I almost forgot to leave anything for myself. Now I am scared that if I am going to go back and date again I’m going to get hurt and heartbroken again. I feel like all men are just the same. I don’t trust all men. My ex destroyed all my hopes that someone will love me for who I am and not just use me. Now I don’t know if I can be a good girlfriend. I am scared to try again and take a risk, especially since I have kids and I don’t want to see my kids get hurt by someone they love. – K

Dear K: There is nothing wrong with being afraid to fall in love again—everyone feels that way sometimes. So fear itself is not the problem—it’s just a feeling and it actually won’t hurt you. The problem comes when you allow fear to limit your ability to move forward. That’s why I’m very fond of a quote by Susan Jeffers: “Feel the fear and do it anyway.” (more…)

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‘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…)

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‘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…)

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‘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…)

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‘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…)

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