Hi Tiger, You were raised a long time ago, so I'm interested that you're still hung up about meeting expectations from that far back in your life. Why have you not yet become independent in your thinking, ethos, daily life habits, from aspects of your upbringing which don't serve you well and make you happy?
Suppose you took an attitude that your and other people's social status doesn't matter? Among my friends are a cashier at the local supermarket and a Lady (titled.) Most are somewhere in between. I love them because we share some interests and values and humour, not because of their social status.
Your loneliness is important. Get out and mix. Don't expect to make good friends or even acquaintances for quite awhile, just focus on being active during the week, in a variety of things you enjoy for their own sake. Try some group things which are feelgood even if they don't create intimacy - such as exercise classes or a choir. Things like book clubs often create close friendships as they get people talking. Likewise art, language and creative writing classes. If there isn't a book group you could advertise to start one up. Just warming yourself up to meet people and feel relaxed and happy and good about yourself when you're around them is the best way to start to overcome the loneliness.