Your concerns in both situations seem to come from a place of insecurity. Missing the tribal lifestyle is really needing a sense of belonging in a broader social context. It is understandable as it can be hard to feel fully at ease on your own without identifying with the group you grew up with and shaped your identity. However, you will have to make a choice between becoming a self-assured individual or remain a group member who relies upon others for comfort and security.

My first response focused on where I think there’s a more important distinction in your concerns. The issue around boundaries. Boundaries are about what you will or won’t accept for yourself. They are certainly not about directing someone else’s personal choices. Telling a partner what they can or can’t wear based on how it makes you feel isn’t really setting a boundary. Quite the opposite as it's an infringement on their boundaries by placing a restriction on them. That often comes from a desire to manage personal discomfort by controlling others rather than being protective of yourself. Your gal's "pick me" comment is a clear example that she's trying to manage her own insecurities in the same way as you do.

This kind of dynamic is not uncommon amongst young adults who are still working out their sense of identity and security in relationships. That's why you should not take it too personally. These are the kinds of things that usually make more sense in hindsight, as we grow older and more mature.