How can I create a new friendship with someone who I’ve known for a long time but have never been close to?
Try to get to know them better. Ask them more intimate questions. When you feel a connection with them, just acknowledge it and say how nice it is. You can always say something like, “This is really nice, we should hang out more often,” and when they agree actually take them up on it and make an actual plan. In order to kind of get in there and get past whatever the wall is that you guys haven’t broken through, you really need to penetrate, and open it up, and ask more stuff, and acknowledge that you like it and that you’re enjoying it. So, in sum, try to get to know them better. Ask them questions to initiate deeper conversation. Acknowledge that it’s nice to connect, and initiate another time to hang out. “Hey this was fun, let’s do it again, what day, what time. Okay, I’ll see you then.”