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.


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