Why Can’t I Meet Anyone And Why Do I Always Feel Alone?

why can't I meet anyone

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

 When a woman emailed me these two questions: 1) Why can’t I meet anyone? and 2) Why do I always feel alone? I had to dig deeper. So, I asked her some questions. I asked about her past, her relationship history, how she met the guys, what the circumstances were, etc.


After hearing some details about her dating life, what I found out was, the answers to her questions are simple: her. In other words, this woman is her own worst enemy, and she is the reason she can’t meet anyone. She is the reason why she always feels alone. Before you think I’m too judgmental, let me explain.


Katz and Stefani Family Law Attorneys


I want to preface what I am about to write by saying I realize that finding love can be very difficult, and that there are so many undesirable men (and women) out there with baggage and issues that go beyond complicated. Dating can be frustrating, exhausting, scary and time-consuming, with a rollercoaster of highs and lows that can lead someone to feelings of extreme disappointment and hopelessness.


But, there are certain people who self-sabotage their chance at real love and a fulfilling, meaningful relationship. Some of the things they do include:

1. Dating married men or men who are in a relationship with someone else.



2. Dating only men who treat them badly.

3. Dating men with problems—alcoholism, drugs, gambling, sex addiction, etc.

4. Dating men who are emotionally unavailable.

5. Refusing to date “nice guys,” and being turned off by men who treat them well or who truly care for them.


Let’s take my reader. She told me that she has been dating a man on and off for the past year who says he is getting divorced. But, he still lives at home, and has taken no legal steps to get divorced. He says it is because the kids are not ready, and he has to sort out some things.


So, one of a few things is going on here. First, he could be completely lying and could have no intention of leaving his wife. The wife might have no idea about his affair. Or, maybe he and the wife are having problems and talking about divorce. Or, he could be telling the truth. But, how healthy can this relationship really be? How do we know how long it’s going to be before he takes action? Is she supposed to trust him and just keep waiting? Also, after he decides to move out and separate, isn’t he going to need some time to adjust from that and heal? He has a whole divorce ahead of him.

Here’s the thing. Doesn’t this woman deserve to be in a relationship where she isn’t a secret? Doesn’t she deserve more of him and his time? Doesn’t she deserve to get the best of what he has to offer? And clearly, whether he is cheating or telling the truth, he can’t give her (or anyone) a healthy, nurturing, happy relationship. All he has to offer is sneaking around, secrets, and kids at home who don’t know their dad is occasionally hanging out with some other woman.

I would be willing to bet my readers sits home every weekend and only sees him for hook ups or a quick drink or lunch or dinner. Then, he goes home to his “family” and she has to go home to no one (she doesn’t have kids) and feel sad and empty and lonely that she doesn’t have all of him. How good is this scenario for someone’s self-esteem? I would think all this situation would do is cause someone frustration, resentment, disappointment and self-loathing. The joy is fleeting.

Before this woman dated this married guy, she was dating an alcoholic, who hit her a few times. She kept getting back together with him and then they would break up again when he became drunk and mean and abusive and sometimes violent.




Before him, she dated a guy who was single, but who cheated on her repeatedly. She found a pair of woman’s underwear in his apartment that was not hers. They broke up for 3 months and then reconciled. She then came to his place and saw a woman leaving. They broke up again, but then got back together. The guy would tell her she was insecure and paranoid, and she would give him another chance.

When people deep down know they are in a relationship that is bad for them, but they stay in it or keep getting back together with the person, all it does is spiral into this bad cycle of ups and downs, disappointment, resentment, anger and self-loathing.

It seems this woman is attracted to toxic relationships for whatever reason. Possibilities include: low self-esteem, a bad childhood that led her to mimic behavior that she saw, no self-love, her subconscious desire to stay single, or her fear of intimacy that can stem from a variety of reasons.

She then shared that she was dating this one guy for a little while but he was “too into me.” She also turned down dates with men for reasons that included a guy being too tall, a guy being too short and a guy who didn’t smoke. (she is a smoker.)

I think this woman, and anyone else who finds themselves asking “Why can’t I meet someone?” and “Why do I always feel alone?” would benefit by exploring with a therapist what the deep-seeded reasons might be.

There is no denying that finding the right person can be challenging. There are countless factors we can’t control, such as fate, timing, and being in the right place at the right time. But, we CAN control the choices we make as to who we spend our time with, who we get involved with, and who we let into our hearts. And if we are making poor choices, then we are hurting ourselves, oftentimes without even realizing it, not only because we are with the wrong person, but because we aren’t free–physically or emotionally, to find the right person.

There is nothing better than a romantic relationship in which you let yourself love and be loved by someone who treats you well, who can give you what you need, and who makes you happy—ALL the time. Love and vulnerability can be scary, but there is no better feeling than knowing your love is unconditional and authentic. That is when you will never, ever feel alone.

Like this article? Check out, “Loneliness: It Might Be The Worst Pain Someone Can Feel”


Buy novels by Jackie Pilossoph



Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

2 Responses to “Why Can’t I Meet Anyone And Why Do I Always Feel Alone?”

  1. Don M.

    Jackie — a good post. Sometimes a good look in the mirror, can help. I didn’t like what I saw, I also saw how I contributed to my divorce. It wasn’t pretty. But I worked on it.


    • Jackie Pilossoph

      That’s great! Many people don’t have the self-awareness to admit fault in any way. that is healthy. good for you!! I wish you all the best.


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