Dating advice for lonely men

December 9, 2023

Note: This article focuses mainly on heteronormative relationship dynamics. We’re also going to be setting aside casual sex and casual dating, which can be healthy and fun when all participants are working with a shared set of expectations. However, such situations often fail to relieve a deep sense of loneliness and may be ill-advised for chronically lonely men – it does not provide the answers to the problems we want to discuss today.

The posmasc community was founded, in part, to address the needs and insecurities of men in honest, frank terms; to validate these feelings of insecurity and offer genuine compassion and advice on overcoming them. Since its inception, we have addressed a number of issues in our conversations, and one recurring theme that many men who approach us are struggling with is dating, romantic relationships, and loneliness.

This is an issue that feminists can struggle to discuss in terms which are empathetic towards the needs of men. We are a feminist group, and as such the issues we reckon with include things like patriarchy and rape culture, and when dating and male loneliness are raised in light of these issues, the discourse tends to portray men unsympathetically, and with good reason. But it is important to reach for empathy and connect with men’s needs on meaningful terms, because absent the feminist contingent acknowledging that need, more harmful communities will step in to exploit these insecurities in men – incels, pick-up artists, and more.

Today, posmasc, a group of feminist men, is extending a compassionate hand towards our lonely peers. Let’s talk.

Loneliness is a brutal condition, and having our romantic needs go unmet is a fate that causes us a great deal of grief and insecurity. Humans are social, sexual creatures, and we can recognize these things as needs that are being unmet, and acknowledge the grief that comes with that unmet need. Men are encouraged by society to “chin up”, minimize their emotions, and put on a stoic face, but let’s be honest with each other: chronic loneliness is an absolutely soul-crushing feeling which can have severe consequences, including anxiety, depression, and worse. Many men have few outlets for dealing with that. It’s normal to feel upset, overwhelmed, desperate, or without options. It’s normal for it to keep you up at night.

We can acknowledge romantic connections as a need. But we should also ask: whose responsibility is it to meet that need? Many men subconsciously assume that it is the responsibility of women to fulfill this need for them; this is not so. The journey towards conquering loneliness begins with self-improvement and the development of abundance and quality in your social connections, romantic or otherwise, from which strong romantic connections emerge naturally.

There is a tendency to fixate on dating and romantic success with women as a lynchpin of your feelings of loneliness, but this is not healthy. Men with this outlook tend to treat “getting the girl” as a social achievement; as a symbol of their social success, and the solution to all of their problems. However, this is a self-defeating attitude: if you approach women from this perspective you will not have success in dating.

Women are not aliens, famously inscrutable though they often seem. They’re just people, much like yourself, and much like your male friends. Success with your relationships with women does not arrive when you find yourself in bed with them, but when you form a genuine sense of connection and understanding with them. Chronic loneliness in men tends to incorporate some degree of ignorance: lonely men often view women as two-dimensional projections of their personal insecurities around sexual “success”, and struggle to acknowledge women as having independent lives, values, motivations, and needs.

You may have great male friends in your life, with whom you have strong connections and companionship totally absent any romantic context. You may not have similar relationships with women in your life; it’s common for lonely men to view all women as romantic prospects, which inhibits their ability to form genuine connections that don’t depend on romance. Women are not looking for romantic connections in a vacuum; the platonic relationship also needs to be strong, and thus this attitude of putting romance on the table first is self-defeating, and may explain the demographics of your social circle.

Or perhaps you do count women among your friends, but you find yourself in the “friend zone” with them. I wonder: why is it a problem to be in the friend zone? The friend zone sounds great! You might need to take a step back and consider the gratitude you feel for having good friends in your life, regardless of gender, and question whether imposing an unrequited love on them (or lust, let’s be honest with each other) is how you can be a good friend to them in kind. Some women may be interested in you romantically and/or sexually, and others might not; you need to develop the social acumen to tell the difference. Those that are not interested in you romantically may still value your friendship, but are struggling to reject you clearly on romantic terms (or you may be choosing not to hear their words of rejection) out of fear of threatening a friendship that they value with you. If your friends don’t feel that they can say “I don’t want to have sex with you” without threatening your friendship with them, then you are not being a good friend.

It’s important to listen to women in earnest. Try to understand them as people, without imposing expectations of providing romance and sex (and free therapy) for you. Consider consuming media by women, for example: go to your local bookstore and tell the clerk what kind of books you like and that you’d like to find female writers you might be into. Study feminism – women have been telling us what they want for some time now, and listening to what they think is a smart move (and it’s an open secret that feminist men get laid more than incels). Go into this with an earnest interest in the lives and perspectives of women for their own sake, and let the romance come later, and be informed by this journey. Your goal is to go from “I want to fuck women”, to “I want to understand women (so I can fuck them)”, to “I want to understand women”.

This is the advice men want to hear, narrowly focused on how they can achieve success with women. But there’s also something men need to hear, both for themselves and for the sake of their romantic prospects: you need to find yourself as a person. In our fathers’ generation and generations before, prior to women’s liberation movements, we were taught traditional men’s values: be a provider and that’s enough. Unfortunately for us, that’s not enough anymore! Women can provide for themselves and they aren’t looking for men with a high-earning job and nothing else, and many men weren’t prepared for that.

In study after study, survey after survey, the number one trait women value in a romantic partner is confidence. You have probably already heard this. But what does it mean, and how do we get it? In short, confidence is an outward expression of inner peace and self-worth. You are a complex person: you have principles and values and interests and hobbies and passions. Developing these will bring you life fulfillment independently of romance, and moreover, it will make you more interesting and appealing to your romantic prospects. Focus on self-development and self-actualization, and romance will get easier. Women will be much more interested in a man who can show passion for things other than his dating life, and it will offer you common ground from which you can engage with her intellectually.

Let me pose to you the following question: assume your inner self-doubt is true, and in fact you are doomed to never have a girlfriend. Does that mean your life will be devoid of meaning, that it’s not even worth living? If so, that’s the problem you need to address, and this feeling is in fact a strong contributor to your romantic struggles. Find your self-worth. Consider coming to terms with those doubts and seeking out ways to make life worth it in spite of that, and, paradoxically, your dating life will probably improve.

Feelings of loneliness and romantic failure are acute and painful. Each rejection feels worse than the last, and they easily compound to foster a profound sense of deep insecurity and inadequacy. Facing these feelings without the resources to process them in a healthy way can lead to self-defeating behaviors that make the problem even worse. The solution is to stop fixating on romance: focus on finding your intrinsic happiness, and view women not as both the cause of and the solution to your loneliness, but as complex and interesting people in their own right whose lives exist independently of your romantic interest in them.

This can seem really hard! It’s a daunting prospect. I get it, honestly. If it seems insurmountable, you might want to seek professional help in finding the things that make life enjoyable without depending on having a romantic partner. If you’re able to achieve this, you will feel much better. Regardless of whether or not your romantic prospects improve, this sets you up to lead a much more fulfilling life – providing more meaningful friendships and a better sense of your personal worth and meaning from within. And, pragmatically, you stand a much better chance at success in your dating life from this position than one of chronic despondence.

This process of finding your own happiness may sound a bit blasé, and certainly quite difficult – it is hard work. But it is also joyful, and important, and rewarding, and I think that you can do it. When you daydream about yourself, what kind of person do you dream of? Do you want to learn a new language, volunteer at an animal shelter and covertly bury yourself in small puppies in the off hours, do you want to go back to school or change careers – and how can you become the person of your dreams? If you can answer that, you might just find that you’ve become the person of someone else’s dreams, too, but more importantly, you will find the joy within. You might read between the lines of this article and suppose that, in short, I’m telling you to get your shit together. To be honest, you wouldn’t be wrong. But getting your shit together is not about suffering your flaws until they’re gone; it’s about finding your own joy and embracing it. The process of getting your shit together should be exciting and rewarding and, though it might be scary and challenging, not insurmountable by any means.

This article does not present a magic pill you can take; armed with our advice, you are not likely to hop on Tinder and bag a hot date for tomorrow night. This advice is the start of a personal journey in which you will prioritize finding the joy in life without fixating on romance, so that, in time, you can share that joy with someone you love. Good luck – you can do it.

P.S. You know how we suggested seeking out women’s voices? This article from Captain Awkward is a good start, it elaborates on this article’s themes and provided some inspiration for the text.

Are you struggling with loneliness yourself, and looking for a supportive community to talk to? Consider applying to join posmasc.

If, after reading this article, you find yourself still feeling overwhelmed, depressed, or despondent, it might be a sign that you should seek out the advice of a mental health professional. Reach out to us and we’ll try to help you find someone.