You've provided a lot of useful information towards coming to possible paths to the goal you've posed.
I've a few more questions mainly around the strictness of your constraints that I hope will clarify the space of reasonable solutions.
I'm also trying to point towards a profile for what you consider the boundaries of an interesting person as well as easy heuristics for filtering to find these people.
Regarding (1):
Can you provide some elaboration around what you mean by an "interesting person?"
What heuristics do you currently use to determine whether a person is interesting?
Generally how long does your evaluation period last?
Regarding (2):
In the past, what kind of traits unify people that know you well and whom you would feel comfortable pulling you out if you were acting strangely?
In the past, have any of these people not stand out in a crowd? If so, do these people share traits that are different from the larger group of people who've known you well above?
Regarding (3):
How strict is this constraint i.e. how far would you be willing and able to travel on a regular (say weekly?) basis for face-to-face social interaction? The answer could be 0...in which case all social counter-parts would have to travel to you.
Is it possible to get into town via public transit such as a bus or train? Do you know anyone (apart from your mom) nearby who might be willing to drive you into town? For those people who are on the margin in your belief of their willingness, have you tried asking them to test the proposition?
How strict a constraint is your psychological problem with breaking routine? Are we talking no behavior modification on your part, and so simplifying the question to finding people who're willing to come to you / alter their behavior for you? Or are you open to exploring routine breaking as a means towards this end?
1) Heuristics: It correlates a LOT with reading LW, and also in general sharing interests and internet-cultural background with me, as well as being generally smart/nice/artistic/a formidable specialist at some specific field.
I don't know what you mean by evaluation process. It's more like a hidden property I collect evidence for or against, so I'll hopefully eventually become fairly certain but new evidence can always change my mind. Also the interestingness of people can change as they learn more or I learn more etc.
It's not rally a very high grade conc... (read more)
An exercise:
Name something that you do not do but should/wish you did/are told you ought, or that you do less than is normally recommended. (For instance, "exercise" or "eat vegetables".)
Make an exhaustive list of your sufficient conditions for avoiding this thing. (If you suspect that your list may be non-exhaustive, mention that in your comment.)
Precommit that: If someone comes up with a way to do the thing which doesn't have any of your listed problems, you will at least try it. It counts if you come up with this response yourself upon making your list.
(Based on: Is That Your True Rejection?)
Edit to add: Kindly stick to the spirit of the exercise; if you have no advice in line with the exercise, this is not the place to offer it. Do not drift into confrontational or abusive demands that people adjust their restrictions to suit your cached suggestion, and do not offer unsolicited other-optimizing.
To alleviate crowding, Armok_GoB has created a second thread for this challenge.