When it comes to affairs of the heart, we are all beginners. Some of us, however, at least speak with authority. Introducing Shon Faye, author of The Transgender Issue (2021) and the forthcoming Love in Exile (2025), whose advice caught our eye. Contact her at DearShonVogue@gmail.com for your own chance at enlightenment.
Dear Shon,
My life is mostly going well. I’ve got a lot of friends I care about, a good job, a great relationship with my family, lots of passions and hobbies, and decent fitness. But when it comes to sex and relationships, I’m just a complete disaster. And my anxieties because of this are making this even worse.
At 26, I’ve never had a relationship. Every attempt I’ve made to form any connection with a woman has resulted in rejection. I’ve had a tiny amount of hookups but nothing more. And it’s honestly tearing me apart. I know a large part of it is because I’m very unattractive, but I also fear that by not having any experience in relationships, I’m clueless as to how to ever start one.
Sometimes I feel like I’m better off just not dating at all. I enjoy other parts of life most of the time. But when I come home at night, I just feel constant loneliness and desperation. Sometimes I feel like I’ve missed out on my 20s and will be alone my whole life. I want to move on from the single life and connect with someone, but the fear of going through yet more rejection puts me off trying to get myself out there.
Lonely Heart
Dear Lonely Heart,
It often strikes me how much modern dating advice and guidance about how to regulate one’s emotions in the face of an ever-changing and challenging romantic landscape tends to be addressed, at least implicitly, to women. Yet research conducted in the UK found that 60% of men have felt insecure when it comes to dating, with fear of rejection, their age, and their appearance being the three key factors. (I noticed your letter mentions all three.) I am telling you this to emphasize that you’re not alone—so many other guys feel similar to you. But you may feel very alone because of how little men talk about this stuff. There’s a sense of shame or embarrassment for men in expressing the insecurities they feel because of how gender stereotypes emphasize that ease and confidence with women should be an automatic part of masculinity. It’s far less stigmatized for women to speak about low self-esteem or a longing for connection than it is for men, yet evidence suggests younger men are lonelier than they have ever been.
I think it was brave for you to write to me so honestly about your struggles with confidence, rejection, and loneliness because, in response to the social stigma against men who try and talk about this, online movements of extreme misogynists play on young men’s fears. It’s clear a healthier conversation about men’s insecurities and fears of rejection is needed, one that does not seek to blame women, and it takes guys like you being willing to speak up.
First of all, I want to remind you that 26 is very young. We’re sold a myth that everyone begins a pattern of serial monogamy in their teens and will have racked up a few relationships by their mid-20s, but this simply isn’t true. I know plenty of people who have not had a relationship at 26. I know some who haven’t at 36! This has nothing to do with their value as people but is more likely due to them having prioritized work, experienced health issues (including mental health), or simply not met the right person. Many people who have had lots of relationships by age 26 feel similarly unworthy because they see so many failed relationships as a sign that they’re not good enough to have lasting love. There’s always a stick you can find to beat yourself with, if you’re so inclined. My point is that you need to untether your sense of your own value from your personal dating history. Another warning: If you do tear yourself apart with feelings of worthlessness now, I can guarantee those feelings will follow you into any relationship and may well sabotage it.
I can’t tell you whether you’ll meet a woman you’ll be able to form a connection with because no one can predict something that is so largely dependent on luck. What I can tell you is that the belief that you’re lacking something, and a connection with a woman will fix it, is not serving you. You describe yourself as “very unattractive.” I have no idea what you look like, but the fact you have friends and family members you care about, hobbies, passions, and a fitness regime suggests that writing yourself off this way might be a bit hasty. Many women are looking for more than conventional good looks. But you have got to work on the desperation you describe because desperation is often palpable and deeply off-putting.
Some bad news: Rejection is part of dating for everyone. You need to accept that it happens to the best of us. I’m afraid if you do want a connection with another person, it’s your responsibility to learn ways of coping and bouncing back with your self-image intact when the other person doesn’t return your attention. If you grow too afraid of rejection, either you’re not going to put yourself out there enough to make connections or you’re going to become resentful and bitter (which women will pick up on and avoid).
You need to work out what works best for you in terms of meeting people. If dating apps, with their emphasis on photos and a few words on a profile, intensify anxiety, then maybe you need to get off the apps. Do your hobbies and passions bring you into contact with new people? Get involved with new activities to meet people and tell yourself you will pursue personal fulfillment rather than the fantasy of a relationship. Focus on becoming a well-rounded person rather than finding a partner. Do you have women friends who you connect with on a platonic level? Getting to know women without any sexual aspirations is something too few men think to do, and it turns women into strange mythical creatures in their heads. Getting to know and value women outside of dating will enrich your life, but it will also help you feel more at ease when approaching women romantically.
If you do want to ask someone out on a date, remember to keep it light, and if you get a no, remain gracious. If there’s one thing I want you to remember, it’s that a woman declining when you ask her out is much more likely to be about what’s going on with her than about you. She may not be in a place to date, she may be getting over someone, she may be involved with someone else, or she may simply not be the right match for you. Try to reframe a no as a good thing: You were clear about your intentions (which is a very attractive trait!), and her no has saved you time and energy. It may take time and a little effort, but this sort of perspective shift can help to take the sting out of rejection and help to separate your ego from other people’s responses.
If you are still struggling with feelings of loneliness and low self-esteem even after trying some of the suggestions above, then I would recommend counseling to look at deeper issues that may be keeping you trapped in a cycle of negative thinking. Learning to be kinder to yourself will be an investment with solid returns for your well-being, whether you’re single or dating, after all.
