Dating is not easy man.
Let me tell you this. Women marry up (hypergamy). This is like the freshman girls only dating the senior guys in hight school all over again.

Think about this for a sec. How come those 50 something overweight dudes get to date (and marry) those freaking hot 20 something ?

The chicks are marrying up. Now you told us that you got a good job. Sorry pal, not good enough. You got be making millones a year to score that.

The truth is that 30+ and/or plus size women is your league right now. Whether you like or not.
And if you marry them, you will be happy and have a happy family.

And I'm serious. Because for the alternative you got change who you are.

But you don't feel like it dating them, right? How can you date women that you feel it's on your level ?
You gotta fake it man. I know this is not really a popular answer, thats why I'm using a throw away account.

This is the old fake until you make it.
And faking it's not easy man, and takes time. And money.

And here it goes my awful advice.
You got learn how to be a player, and there is no school or blog that teaches you that. I'm not talking about you should become those kind of instagram douchebags. But you got develop some game. Be comfortable being the center of attention. It doesn't matter if you got six packs. It really doesn't.

Here is my really awful advice.
You got spend some money with those $500 escorts. I'm not saying you should sleep with them. But it's your money, and they are there to spend time with you. And you got learn how to deal with freaking hot women.

Can you imagine, you having a steak and lobster with a 5'11" hot brunette in a nice restaurant. And that she is in a date with you because you payed her to.
Just let that sink in for a second. You walking from the parking lot into the restaurant with a escort and people will be checking you folks out.
WRONG. You should drop your car with a valet. And you better be on a niceish car. And have champagne. You are putting a show man. And you should have fun. You may easily spend $1000 on this.

I know this is awful. And in a way is. But you are teaching yourself a few things. How to deal with attention. How to make the girl you dating feel special. And that counts a lot. Just the way you walk will change.
In this kind of scenes everyone will be looking at you. You gonna be the center of attention and you are used to it. And you will learn how to be comfortable with it. And you should like it. Because most women love attention. Why do you think they spend so much time getting pretty for a date ?

Let me tell me a story. I'm a divorced 35 yo brazilian coder. I live in Miami this days.

There is a restaurant at 9th and Irvine in san francisco called Park Chow I used to go a lot soon after I got divorced. It's a cafe/restaurant and I would sit outside and be drinking some white wine and reading a book on the weekends afternoon alone. Around 5pm or so over the summer the place would be crowded and there would be a waiting list. Whenever I saw a group of girls adding their name to the waiting list I would offer to share the table. And that would happen a couple of times a month. They were mostly tourist looking to have a good time.

And that is the kind of game i'm telling you should learn from dating the escorts. How to play the playboy.

This is getting to long and I bet folks in here will no agree with me.