Will I have to become how my older brother once was?

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My older brother has had more girlfriends than I have and probably ever will. We are only 14 months apart but are completely different individuals. Unlike me, he always had friends come over, threw parties, girls chasing after him, and was high fived for being an alpha male. He was very loud, wild, and knew how to play mainstream society's games. I was stuck in his shadow at school and sometimes even confused for being him. Everything I tried to do from trying to get a girlfriend to starting or joining a rock band failed while he seemed to have everything come to him as if God (I am not religious anymore) blessed him while I was considered the black sheep.

I do realize that despite all his relationships he's also had a divorce, two cancelled marriages, has four kids that take up all his time, and his current marriage is very turbulent but it feels like he could easily go back into the dating scene while I can't even find the entryway to it. However, he's told me that isn't the case and that he would actually trade places with me if he could. I don't think he would want my chronic singlehood, though.

I don't hate myself as an individual. I like that my favorite band is an orthodox one like the Melvins, I prefer anime over reality TV, I prefer reading good books over Facebook posts, and I don't let society's prejudices influence me. I just hate how my individuality hasn't paid off in terms of making my dreams come true.

Divorces and kids are a hassle. Trust me.

You don't want to be in your older brother's shoes. Trust me.

He does tell me he has hardly any time for himself because of his kids. He and his wife also had a cancelled marriage the first time they tried to make a family. Even today, his wife still doesn't like the daughter he had with another woman. She's very hateful and selfish as well as manipulative. I don't feel jealous of their marriage on both a physical level and an emotional level.

I am surprised to here him say he wishes he could trade places with me, though. I am not saddled with his responsibilities but I wouldn't wish my social isolation as well what feels like my permanent inability to get into the dating game. It feels like wanting to play an instrument but you live in a remote isolated area that doesn't have a music store.

Social isolation sucks.

Having to pay alimony sucks even more.

Even if you wanted to become like he was you probably wouldn't be able to. That's just not the kind of personality you have. Don't try to follow after him to get the things you want, create a path that suits you.

As for him wanting to change places with you if he could, well... it's common to think that the grass would be greener on the other side of the fence. He sees your freedom, but not the loneliness it brings while you... see his social life but have no full understanding of the responsibilities and hardships it brings. Don't feel bad about it though; many things are hard to understand if you don't have similiar experiences.

The grass is not always greener on the other side, and certainly not in this case...

It would be impossible to be like him anyways, because you're not him. He's acting in a way that's natural for him, as are you.

One thing that seems more and more apparent in your posts Marknis, is that you assume you're a better person than 99% of people around you. In some ways, you're actually more close minded and judgemental than the people you accuse of such things.

Trust me, between overpopulation and cost, kids are grossly overrated! Go to a Disney on Ice show and see how expensive food and souvenirs are and I guarantee you'll never want to have kids again!

Seems like I would like you better than your brother.

I fell for my boyfriend because he's not trying to put on a show, unlike most guys I've met. He doesn't try to act tough or prove himself "manly" for anyone, which is very nice because I (and many other ladies I know) freaking hate guys like that. I like him because he's kind and genuine and have interesting thoughts about all kinds of things, and demands as much alone-time as I do. And we were both "chronically single" until we found each other.
Also, no such thing as dating was involved. That stuff confuses me. We became friends by accident and then biology did it's thing.

Of course, no one can promise that "one day you'll find a girl who'll love you for who you are" but I can assure you that it won't be easier to put up a show to get a girlfriend. If that happened, she would love you for who she thought you were, and not only would it be exhausting for you to keep that show going, you would probably not even like her very much.

It sucks being isolated, but it sucks even more to be in some sort of fake forced relationship.

Truthfully, I wish I could bypass dating and have a friendship that evolves into a relationship. It's just that so many people around me use the term dating and I see things like internet dating, speed dating, and so forth that it makes me feel like I have to learn "the game" or else I will just continue being alone.

Even making friends feels like a mountain to climb for me. People tend to be absorbed in their cellphones and have an aura that comes off to me as "Don't approach me".

Well, it's definitely easier to get a girlfriend if one learns that game, but I think most can agree on that game being mostly BS. It's why so many relationships fail, because people put up a show in order to impress each other, and then they get disappointed as soon as the masks fall off.
If you were to get a girlfriend by pretending you're someone you're not, you would both get disappointed, because you can't keep that game up forever.
It's of course harder for the weird introverted outsiders to find someone we're compatible with. Maybe because there's fewer of us around, and maybe because we just don't approach each other (that's why my friends are all really extroverted, because I don't make friends - other people make friends with me) but there are certainly other people out there who prefers interesting conversations about anime over partying in a club. They're just way harder to find - because they're at home watching anime.

Every time I read or hear dating advice aimed at men I think 'that wouldn't work on me' so I don't bother reading the stuff aimed at me about men.

Your brother might not really want to swap with you but it sounds like he's envious of some parts of your life. It might be good to pay attention to those parts, as we do all seem to obsess over our negatives and then think everyone else sees us as negatively as we see ourselves.