This question is divided into 2 parts,the first,and the second.Each part of the question can be answered independently, although the answer to the first can affect the second.
You can never be fully comfortable about yourself. There will always be frustrations that you will have about yourself,for various reasons,and after all we are only human. If God has already put you in this situation in what you are now then there is really no reason why you should keep concentrating on how comfortable you are in this situation.However,if you look at theoretically in the factors that can and should determine one's comfort with oneself,then there are many,many considerations.
The only way to true happiness is through holiness ,and happiness provided by earthly means are only temporary. Fitting in can provide a certain comfort as it provides more opportunities for social relationships,and as such it can provide temporary happiness. However,this is not the only means,and is also not a necessary mean.
The dictionary defines being popular as being liked or admired by many people or a particular person or group.A person who is popular tends to have many supporters,and as such appears to have it's opinions backed by the majority,and this can prove tempting to one who wants to have his/her opinion accepted.However,having a few people to discuss these kinds of matters can refine them before having them thrust into the public.Once information gets out into the public,it can be rather difficult to change,and this can prove embarrassing to whoever starts it.
Personally I don't see any reason that we have to put restrictions on our activities in order to not harm ourselves.For others,though,you can either remove the means or remove the reasons.Removing the reasons that one would hurt oneself is better than removing the means,although more difficult,as when the reasons are removed the means do not need to be considered any further.If the means are removed,the reasons still exist,and the possibility still exists that a person would find an alternative mean to harm oneself.
The opinions and behaviors of the people in this book,are they exaggerated or are they an accurate representation of an American society? Do they apply to us as well?