I recently had a friend tell me about her newest obsession: Caroline Calloway. She said that she started legitimately following her about a month ago after another (now ex) friend “hate followed” her and spent six months gossiping about her. All of that (ex) friend’s venom actually only made my friend intrigued enough to research her herself. Now, she’s a fan. And, as of last night, I am too.


Because I identify with her and I think she’s brave and meaningful.

Yup. I do.

It’s incredibly hard to put into reasoned and discernible sentences the way social media has affected my generation psychologically, and to outline the ways we have adjusted to the shifts in our world in a way that generates empathy from our parent’s and our older cousins’ or siblings’ generations (the Boomers and X). But to make a cultural reference some Boomers (and maybe some of “The X”) might relate to, Caroline Calloway reminds me of Janis Joplin. …But also, a little of Zelda Fitzgerald and Truman Capote.

It’s this (Southern?) aesthetic of sadness, intense (perhaps not always totally authentic?) self-reflection, love of beauty, cautioned empathy, poignant mirth about futility, and genuinely risky openness. Where past generations engaged in forms of self-harm like drug use or greed out of a sense of injustice (and the malaise and depression that follows) perhaps my generation overshares. We protest by telling you things that will make you hate us (because you’re tragically predictable), feel too much or make you deeply question our motives and that will, therefore, allow us to cathartically bleed from our souls. We’re angry but we aren’t supposed to be… We aren’t truly allowed to be. So we shock you with the truth one way or another. And, some of us find each other and relate.

We can’t use sex anymore. We can’t truly use violence (some have tried, but thankfully, many of us don’t want to). And, of course, we don’t want to just die. So…how about being painfully obvious? How about embracing “the weird” and “off-beat”? And what’s more weird and off-beat than being very honest? Bizarrely open? Too “out there” with ourselves and our lives to be “taken seriously”. Also, we long to be heard. Just like many of you did…

Yes. A well-off, very well-bred, Cambridge educated young lady with nice things can be genuinely broke.

Think of all the struggling artists of the past from a wealthy pedigree. They existed (especially in an expensive cultural mecca like NYC). Just because you have family money, connections, a world-class education and etc. doesn’t mean you won’t be occasionally broke if you’re trying to live as an artist. My parents (both Boomers) came from decent enough backgrounds but my art major mother and sensitive, well-educated father didn’t give me as many blessings (until my mid 20’s) financially as they had growing up (they eventually inherited an amount from their parents and grandparents and my father has apologized actually…). It happens.

Unless you come from extreme wealth and inherit at least 20 million you have to work at some point (or sell something). Or, if you want to raise children and stay home, etc., you have to be a part of a team effort with a partner or spouse who works (or has that 20 million).

And it truly is overwhelming to deal with this world of the 2010’s. …There may be some criticisms of Calloway that are more well founded than others (maybe she could be more a little more frugal), and I don’t obviously know her well enough to discern her ultimate truths but…if she’s “for real” then she’s amazing. Her art is too. And to some degree, I think she *is* her art. …It’s not everyone’s cup of tea, but I like it… It’s subversively offensive and beautiful and sincere and hopeful and utterly depressive and moving and humane all at once. It’s very Millennial.

So, think 1920’s, boozy (which translates to today’s thankfully sober but has potential to “get in trouble”), beautiful-flapper-wearing red-lipstick, chewing gum (secretly to annoy very particular people)…listlessly lounging on a chaise. …Although undeniably engaging, she’s gifted to the point where she can appear “ditzy” to the untrained eye.

…She feels deep pain over her older brother’s death in WWI and wonders if anything matters more than true love in all its forms. But, she’s incredibly happy to be alive to reach adulthood (her favorite little cousin died of the flu in childhood)…and so she often feels a sincere joyful thankfulness…but…all of the death, the tumult, the arrogance of the world around her…the simmering (albeit blighted promise) she has, and the need for release, forces her into a state of constant expression. Her life is art. As a brilliant friend in college once described about his view of his own personage (IQ in the 160’s), she is her own “magnum opus”.

It’s not neat, maybe. It’s not always palatable. But it’s (possibly and hopefully) real even if it is more of an (honest) interpretative dance of herself than what you’d see in her most sacred private diary.

Now, I’m not saying I’m in that league as an artist (although I’d love to be a good novelist someday) or am the lady above, but I think I might “get it”. And I am thankful for Caroline’s existence.

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