A question of logical vs. emotional: If you surround yourself with friends who are fun to be with, but make you feel awful and inadequate in certain situations, is it better to end the friendship and be alone or stick it out and deal with those emotions?

neither. you talk to the friends obviously. if they are so fun to be with and are such great friends then they shouldn't be making you feel awful and/or inadequate.
confront&deal with the problem. but never "deal" with emotions.

scribble it down.