Do you ever let yourself be vulnerable in front of others? Are you open about being insecure? Do you make fun of yourself? Are you able to express self-deprecating humor? I don't know all the details, but just from what you've described, I would suggest you try being really open about how you feel--that you're not interesting, that you pursue things to a high level but are never OK with yourself, etc.--and simultaneously try to find the humor in it. In my experience, people respond to that.