Ask Beastly: How to Find Confidence

A reader has no sex experience and no confidence. Here's my advice.

My name is Alexander Cheves. Lovers call me Beastly. I write about sex. 

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Hey Beastly,

I don't want to take up all your time by asking a bunch of difficult questions in one email hehehe....so I thought I'd start off by asking just a few. What's the best way to meet guys if you are afraid of rejection and insecure (ie. won't use apps or approach people in a bar, club, etc...)?

Hi friend,

Your question is rather long so I've broken it up into sections and given my answers accordingly.

There is no "best way" to meet guys that don't involve some risk of rejection. I empathize with your plight. I am still frustrated by how few ways there are to meet gay men. If you won't use hookup apps or approach guys in a bar, you've cut two major meeting methods I know of, so you will have to get creative.

Why the aversion to hookup apps and bars? Gay bars are our chapels, the places where we have long congregated to find community and friendship. You may want to rethink your refusal to visit them. Everyone is insecure in a gay bar, but that insecurity slowly wanes as you get more experience in them.

Like many young gay men, I was a mess during my first year going out. I drank too much, had poor social skills, and made many mistakes. The seasoned gay men at the bar knew what I was doing — they had seen this same process played out countless times with youngsters over the years. They knew I'd figure out the space and, eventually, I did. They watched me get comfortable and I watched the change happen in me. That is how it happens. 

Regardless of where you try to meet men, you will probably feel insecure, and you will have to face the possibility of rejection. Your insecurities will always be present, as there's no magic formula for making them go away. But don't let them keep you from others. Insecurity and rejection are unavoidable parts of dating and human interaction. Everyone must face them.

I'm ashamed of my lack of experience at being 49 years old. I used to weigh 419 lbs. Between the period of 2001 and 2011 I put on about 200 lbs. I lost the weight between 2011-2013 by working out. I stopped working out last April when I wasn't meeting guys. I just figured it would all happen when I lost the weight because of course gay men are all visual. I didn't count on being so afraid of rejection and insecure because of my lack of experience (not having been with anyone since 2000), I barely remember what it is like or what my sexual role would be (top, bottom, etc..). No one ever spent time with me to show me which one is better or what I'm comfortable with as each person I had sex with was someone I met in a bar when I was drunk, seems to be the only way for me to meet anyone once my social anxiety was lowered.

It's not easy to lose that much weight, so congrats! But it sounds like you now need to take care of some inner stuff, some emotional and mental wounds. There is no imaginary threshold of weight loss or bodily beauty at which point you cross into the welcome area of gay body standards. There is no minimum requirement to reach the approval of gay men. Different men like different things, and no matter how beautiful you look, there will always be some gay men who refuse you. That's just how it goes. The social gay scene is fickle, fleeting, imagist, ableist, and ultimately very punishing and toxic if you gauge your value as a person based on it. There is no border you can cross after which all the work of meeting people and discovering sex is done for you. No matter what you look like, you still have to practice sex to get better at it. It's not automatic or easy for anyone. I know many hot porn stars who are bad at sex.

Take time to set goals that exist solely for you, not for your idea of what gay men want. You need to be good to yourself first, regardless of others and their opinions. You have to see yourself as worth taking care of. In the words of RuPaul: If you can't love yourself, how in the hell are you going to love anyone else? Really sit with those words. They're the truth.

I was a virgin til I was 28 and I stopped having sex when I was 32 not by choice but I guys started meeting each other on AOL instead of in person and quite frankly I'm too uptight to talk about sex, meet guys online because of the above issues.

How does one ease themselves into be sexual when since it involves someone else besides yourself (obviously lol) they have to be interested in you?

I'm afraid no one I'm attracted to is going to be interested honestly since I've gained weight this past year from not working out. I'm trying to get motivated to start going back to the gym, especially since I've been paying for my membership every month since then. Since no one seemed to be interested before after I lost the 235 lbs I told myself just to 'forget it', now rethinking that.

Buddy, you need to do more than rethink that. You need to reappraise your reasons for going to the gym. And reappraise other things too — your life goals, your relationship goals, your sex goals, all of it. The fact is, you have some work ahead if you want to get out of the emotional place you're in. You have to take a leap. I believe therapy and counselling are immensely helpful, and naturally, I suggest seeking a good therapist — everyone needs one. A therapist will likely encourage small actionable goals. They might ask you to discuss your attempts at taking these steps and maybe even write about them, and I think that's a great idea.

Action is how you save yourself. You're seeking magic words that will make everything easier. There are no magic words. If I had them, I'd be a very rich person. 

It's a tough fact, but in love and sex, no one is coming to save you. You can't be uptight, closed off to sex, and unwilling to put yourself in the social arena and then expect your situation to improve. If you want a sex life, you have to fight for it.

There are other ways to be healthy outside of gyms, so if you don't enjoy working out in a gym, stop paying the membership and find some other activity that releases endorphins and gets your heart beating and makes you feel good. Swim or climb trees or go hiking or build sand sculptures on the beach. All these things lead to happiness and health. And remember that no body type will make you completely happy. There are countless miserable gay men with muscled bodies, and every steroid injection and workout does little to make them happier.

Inversely, some of the most confident and sexually inspiring people I know are fat, disabled, neurodivergent, or suffer from mental illness. You must find a way to value your mind and body that exists apart from the cultural standards you perceive as ideal. I know that's easy to say, and most days I struggle to do that (as does everyone). I don't have the body I want, but I've put in the work to love my inner nature — my mind, my tastes, my will — and that "core," what some might call self-esteem, gives me the fuel I need to stay healthy. I want my "outside" to carry and represent positively all the good inner stuff I hold inside.

I've written a piece in The Advocate about rediscovering your sexual self — "24 Ways To Plunge Back Into The Joys Of Gay Sex." Read it.

I'm frustrated, confused and somewhat sad about it. As I think I've mentioned before I think I'll have to move back to Atlanta before anything will change. I don't have any friends where I live up here in ********* so I don't go out. I used to but most everyone else here goes out with friends and I'm just too shy to go up to introduce myself to anyone.  Figure I need a wingman of sorts.

Thanks in advance for your kindness and understanding cos it took a lot of courage for me to tell you my story.

I know it took courage, and I'm glad you did. I want my answers to be sweet but blunt. You need to stop waiting for something to happen — moving to Atlanta, losing weight, and so on. If you're not willing to do the work, you're not really seeking improvement. 

A struggle of mine is "destination addiction." I fantasize that my next place will be the "right" one — the place that changes my life, solves my problems, and makes everything better. On paper, it sounds ridiculous, but I've hopped from city to city doing just that, and each one has been harder than the one before. I'm not saying Atlanta won't be good for you or that you shouldn't move there. But if you struggle with going up to someone at a bar where you are now, you will struggle to do so in Atlanta. The city won't fix your insecurities for you. 

Here's the thing about confidence: most people struggle with it. Confidence is one of the few things I know to which this applies: you fake it until you make it. Make confidence a performance. In doing so, in time, it tends to become real. I don't know how that works, but it's true, at least for me. You have likely met people who overcompensate with strong, loud personalities who seem very confident, and over-performing often is an indicator of crushing insecurity. But that's how those people beat the negative voices in their heads. Performative confidence is a sustained, daily attempt to be confident, to not let anyone see the cracks. Performing confidence may not be the healthiest recommendation, but it's the only one I have and it's what worked for me. You perform until the role feels natural, like reciting a mantra in meditation. You do it over and over until, voila, it does come a bit more naturally and feels a bit less fake. You fake it until you make it.

I performed, faked, and overcompensated for my lack of confidence for years until one day when I realized that I didn't have to perform as much, because, along the way, I found tricks — conversation starters, little social crutches, lines, looks, and so on — to lean into. I still have to perform confidence all the time when my body doesn't look how I want it to look or my sex life is less than stellar. I still have to provide answers to people and speak to strangers and provide nice experiences. Sometimes I have to speak on the radio and in front of audiences, even when I have crushing self-doubts. So I fake it as best as I can, and when the performance works, I get a boost — my fake confidence becomes a little real.

I feel your sadness and I know you are frustrated. Please allow this to be empowering: you are the only one who can save your life. There are many men out there like you — men with little or no sexual experience, who look at their bodies and wish they saw something different. You are far from alone. Many men are looking for a guy like you and are waiting for you to make a move.

Love, Beastly