i find other people's finances SO confusing. there are two moms i hang out with on a regular basis. one is closer in age, we really have a lot more in common in terms of interests etc, but i honestly do not understand how they survive month to month. by all accounts, our income should be higher or pretty much the same as theirs, yet she goes shopping ALL the time, her dd always had really "cool" clothes, as do her and her husband. they go out to eat all the time, live in a pretty fancy neighbourhood, etc. i would love to have her lifestyle and i find her taste in clothes to be excellent, so i know how much she's spending on everything, because i've looked at the price tags. a few years ago, it would never have occurred to me how much of my monthly budget designer jeans, collector sneakers and new tattoos could eat up, but i do now! she doesn't complain about finances the way you describe (i couldn't stand that!) but she does comment on how much money she's spent on clothes quite frequently.
honestly, in the end i find it much more relaxing and fulfilling to hang out with the other mom, who is in a totally different stage of life, not that similar in interests, but who lives her life in the same frugal vein as we do. even though they have their own house, two well-established careers, they still budget similarly to us, and thus we are a lot more compatible when it comes to outings and even just hanging out.
anyway, i'm not being judgmental about these women's spending habits at all... they might have sources of income or expenses i know nothing about, but on a day to day basis, i find it easier to hang out with a woman whose spending is similar to my own than a person who spends very differently, even though personalities and interests would suggest otherwise. what i'm saying is that crunchiness aside, finances are a big part of lifestyle, and have a lot to do with compatibility in friendships.