I find it difficult to make friends. I've got some friends and had some in the past but when I analyze how we became friends it’s almost always either via someone else (usually a friend of my husband or brother) or because they made friends with me (and are generally extroverts who love the sound of their own voice). So the actual making a friend bit wasn't my doing if you see what I mean.
I'm quiet and was painfully shy as a teenager but have mostly got past that now. I'm good at making acquaintances and am willing to get out there and meet new people but seem to struggle to make the final leap to friendship. I do make requests to spend time with people but often they are either evasive or never seem to take us beyond the reason we met (e.g. our children).
I've seen reports that moving a lot as a child can affect this ability and this is certainly true of me as I moved 5 times before the age of 13. What crucial social skill have I failed to develop and how can I learn it now?
It’s difficult for someone who doesn't know you to speculate about what’s wrong in your specific situation. You’ve stated that you are shy and often need a “wingman” to bring you out. That sounds like a pretty adaptive strategy and I think you deserve some credit for making those friendships happen! Not everyone is outgoing and comfortable, and hanging out with people who are can help you connect with others is a useful approach.