Dating - when do you just realise it won't happen?

I think it would be silly for me to give you advice since I'm a lot younger than you but as far as I know, there's only one hope for us fat ugliest which is make money. The rest will come by itself. I learned this by chasing girls, and I assume it's the same with chasing guys. Think about it, no one is attracted to us, but EVERYONE IS attracted to money.

 

Ah trust me my friend, as long as the money is there, they ain't going nowhere. Now if you run out, then you have a problem.

 

OK, 2 fast items:
Join the gym and go every day 1hour at least.
Ask a woman to style you up, give you honest advice on your appearance. Can be just an acquaintance.

 

Ugh, I relate.

 

Don't accept you'll never find someone. There is a special someone for everyone on this planet. For some it will be a tougher road than others.

Did you ever ask feedback why they never wanted a second date?

It seems you already reflected why no one is dating you. I didn't have any luck myself, until I got a haircut, lost a lot of weight and now I get a lot of matches on dating apps. Most importantly it gained me a lot of confidence.

Don't give up and work for it. You will find someone in the end.

 

-double-

 

Why not adjust your target if you're close already? It sounds like having a target was a motivation for you, you might as well keep it going until you fit 'gay community standards', if that's something you think will make you happy. If you're happy with keeping the target as it is, then fuck the standards. You'll find someone eventually, and by not falling into the standards bracket you'll avoid the shallow people anyway.

I'd second asking a female or a gay male friend about some style/haircut tips. A few changes can make all the differences. Dress for your age and go for that handsome middle aged guy look. Black is slimming, and darker colours are in right now. Avoid stripes of any kind as they can be unflattering. I always think facial hair and some minor greying can be attractive in guys around your age. It makes them appear to have the wisdom of an older guy but the looks of a slightly younger guy. A haircut and wardrobe that reflects this can do wonders.

Another important thing to remember is to feel good about yourself. When you conquer your insecurities and find bits about yourself that you love it will shine through to other people no matter what. I've never found people interested when I'm looking - you're more likely to find dates when you don't seem to be looking for them as you appear less desperate and as if you have lots of other things going on. And failing everything, be funny. Even at my least confident I've been funny and it's helped me through.

 

I think part of it is confidence. Confidence is sexy and makes people much more attractive than they really are. Have you spoken to a therapist about these issues? It might pay off to find out if there are underlying issues that are getting in the way of a relationship. Just speaking from personal experience - I didn't think much of therapists until I had one, and she really helped me learn a lot about myself and its had a big impact on my life.