I agree with you on not being able to come to terms with spending that extra 60 cents, gets me all the time with food purchases and that sort of stuff. The difference is that I wasn't born with a silver spoon in my mouth, it's out a mostly sincere frugality. Who doesn't want the people they meet to like them? That's human nature, you don't want to go around isolating yourself from everybody that you see. As for the milkshake, I would just go out and buy one and enjoy the time spent consuming it. Sometimes you need to get by on the little things.
I have ended up walking to go get a milkshake, but I would say that part of the appeal is that I don't have them very often. I really should try enjoying small things more, I can get caught up in my thoughts pretty easily. As well as being frugal - going to the grocery store is a fun game of what percent/how much money I can save by buying things on sale - even though it's not a particularly large sum of money. If you couldn't tell, I also get caught up in being self-deprecating, guilty, and negative, not so much because I am all those things all the time, but that being the opposite feels disingenuous. It's a bit of a defense mechanism, so to speak, where being preemptively self-deprecating is an attempt to cancel out any sense of ego that comes out, which is an odd thing to combine with a variable amount of self-confidence. All of this stuff comes out when I spend too much time alone, thinking. Thank goodness for music.
Well yes, the more often you do something the less special or unique it seems. Not to mention the health effects of getting a milkshake on a regular basis are not very good! That's something is fun for you, but is necessary for other people, it's good that you even think about it. At least that's how I feel. I have noticed that, and it reminds me very much of a friend that I have here at college. I think that might fit in with you're not wanting to be disliked immediately part, people aren't as warm to somebody who shows an ego. Meanwhile, somebody who can take themselves lightly is usually regarded in a better light. Music is a great thing, isn't it? Hope you enjoy your milkshake!