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…)?
There isn’t a best way. I’m still frustrated at the few ways there are to meet guys. If you won’t use hookup apps or approach guys in a bar, you have to get creative, because you’ve nixed two major social venues for gay men.
Regardless where you try to meet men, you will face the possibility of rejection. Your insecurities will always be lurking, looking over your shoulder, whispering in your ear. Don’t let them keep you from doing what you need to do.
Insecurity and rejection are unavoidable parts of the sex and dating game. Everyone has to face them. You can’t live without facing them.
Well, you can, but that’s a life without others. To meet men, you must put yourself in the arena. No one is going to come to you. You have to do work.
Guys may come to you part of the way. If you put a picture on Scruff, they will send you messages and pics, which may be the ego boost you need to get through your day. But messages and pics don’t fix loneliness, as much as we try to make them suffice. They are not enough. You must meet someone in person.
When you do, he may refuse you, reject you, or flake out. Or he might be interested. The only way to fail is to do nothing.
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 I applaud you for making yourself healthier. While that’s a big accomplishment, it sounds like you did it for the wrong reasons.
Here’s a confession. I don’t go to the gym entirely for guys. That may be what it looks like, and that’s partly true — like every gay man, I want to look good, and I feel pressure to fit a mold of attractiveness. But if I don’t go to the gym, I won’t sleep.
I don’t vent stress well. I need to exhaust myself — otherwise I’ll lie awake running through my litany of tasks and assignments. I need to get out of my head for two hours. I keep my stress and anxiety running a degree under “panic mode.” The gym affords me two hours to stop thinking and focus on my body.
I gym for me, not others. If I did it solely for outside validation, for the fickle approval of gay men, eventually I’d quit. External motivation is not enough to keep pushing yourself when you’re tired and would rather be doing something else.
Take some time to set goals that exist for you, not for gay men. You need to be good to yourself regardless of their opinions. You have to see yourself as worth taking care of. Regardless who is in your life or your bed, we live and die alone. We face ourselves as single entities. Others come and go, but your relationship to self is lifelong.
This is why you must put yourself in the sex/dating arena. You have a need for others, one we all share. It’s why you must figure out, awkwardly and uncomfortably, what kind of sex you like and how you can get it. Because you have a need that is your job to address.
The concept of sex and dating as self-care, self-maintenance, is fundamental to my philosophy and is something that often gets overlooked in the language of relationships — language that often frames the whole thing as something done for others, a service you provide, a set of needs you must meet.
Wrong. We are selfish creatures playing a selfish game. Selfishness on a human care level is not the demonized flaw you think it is. Selfishness generates goodwill and benign reciprocity and healthy, polyamorous pairings and confident sluts. You’ll never get anywhere until you accept the concept of your own sex, your own intimacy, as a job you must undertake, something you must initiate. A therapist, escort, or sex coach may help (and all three are recommended) but you have to seek them. It’s in your hands.
That first step is finding the courage to put yourself in a sex/dating arena in which you might feel uncomfortable. Unfortunately, only a few are afforded to you, so you must pick one. It may be Grindr, Scruff, some other app or website, a community support group, a gay-heavy gym, a gay hotspot, or something, but you must pick one.
Note: I didn’t list “gay bars,” because it sounds like bars aren’t helping you. Stay out of them for a while. They’ve taught you two falsehoods: That all gay men are superficial, and that you need alcohol to be intimate.
Gay men are more than how we see them at bars. Remember that. Also, consider going sober for a year, especially if this is the year you want to see changes.
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.
Don’t just rethink that. Reappraise your whole reasons for working out. My above response addresses your motivations for the gym.
If you’re going to be a gym guy, do it for you. If you don’t enjoy the gym, stop paying the membership, and find some other activity that releases endorphins and gets your heart beating faster and moves your body and makes you feel good. All those things lead to happiness and health.
Take it from someone who talks to many people about sex: Few people are comfortable talking about it. Most are not. But you have to get comfortable talking about it a teensy bit if it’s something you want in your life.
Humans can’t read minds. You don’t have to be a sexpert or know the intricate ins and outs of fisting or how different lubes work. But you do have to at least be able to say what you want, what you like, and what turns you on.
I’ve written a piece 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 did, and I’m grateful you did. I’m worried my answers seem harsh. I also apologize for how long it took me to write this reply. It’s been a busy few months.
I want my answers to be sweet but stern. I want you to know how serious it is that you take a step in a good direction and focus on sex as self-care — life depends on it. Loneliness kills people.
One of my personal struggles is “destination addiction.” I fantasize that my next location, my next job, my next date, and my next gym will be the one that fits — the one that changes my life, eases my problems, and makes everything come together. On paper, it sounds silly, but I can’t tell you how many nights I’ve driven home certain than the next place will be “the one.”
We all want a savior, whether that’s a new city, a new partner, or a man hung on a cross. I’m not saying Atlanta won’t be a good move or that you shouldn’t do it. But if you struggle going up to someone and saying “hi” where you are, you’re going to struggle doing that in ATL.
I know you’re sad. I feel your sadness, and I know how frustrated you are. I know how crushing it is to think you’re not enough, that you’re somehow lacking. I’ve been there.
You need to give people more autonomy than you are. Just as you must acknowledge your own power, you must acknowledge the power of others. People don’t behave the way you assume they will. They will surprise you. Don’t write their actions. Don’t assume they’ll turn you away or lose interest just because you lack experience. Don’t assume everyone’s a pro, and you’re the lone beginner  — you’re not. Don’t assume everyone wants a gym body. They don’t. I can point you in the direction of many men who prefer natural bodies and chubby boys.
It’s tempting to assume you know how people will see you. If people were that easy to predict, there would be no mystery in the world, no guesswork in sex, no riddles to figure out. It’d be a horrible world to live in. The guesswork and the uncertainty make the magic of human connection beautiful and rewarding when it happens. It’s a science you’ll never master, an art you’ll never perfect. Thank goodness for that.
There are many, many men out there like you — men with little to no sexual experience, who see themselves and their bodies and their experience and are toeing despair. Don’t despair.
You have work to do. Read the article I linked to. Do what it says. Start seeing your body, your confidence, and your sex life as an epic adventure, a journey you haven’t started. It may take longer than a year. It may take longer than two years. But you’ll get there.
Much is in store for you, but you have to take the first step out the door.

Writer, blogger, illustrator, kinkster.

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