‘I’m Pretty When I Cry’: Female Suffering, Emotional Authenticity and the Digital Age

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“I’m grateful all the time / I’m sexy and I’m kind / I’m pretty when I cry.” Olivia Rodrigo sings breathily, with a sarcasm so sickly-sweet it borders on threatening. These lyrics, taken from feminine-rage anthem all-american bitch, have been swept up by young women across the internet seeing their own experiences through her eyes. For a certain demographic, TikTok’s For You page is now rife with wide eyed stares and grins made up of gritted teeth, deeply resonating with and celebrating Rodrigo’s honest frustration, finding some form of release.

The song itself is an Avril Lavigne style pop-rock banger for the social media generation, fuelled by clippable, caption-ready anti-affirmations mocking the often oppressive landscape of girlhood. These closing lines though, as liberating as they may first feel and can be, also form part of an undeniable tension rife throughout the feminine experience to expose an ugly truth: Most, if not all, of us have wanted to look hot when we cry. 

The aestheticisation of women’s sadness is nothing new: Literature, cinema and art throughout history has documented female tears through a pervasive focus on beauty. In recent times, Lana Del Rey pioneered a sad-girl aesthetic long before Rodrigo’s time. Her own track “Pretty When You Cry” was an anthem of an era, entire Tumblr blogs dedicated to mapping this specifically female coded sadness through smudged kohl eyeliner and Vogue slims. Sinisterly, some claim that crying on camera can be considered a “new kind of porn”. Whether it’s Roy Lichtenstein’s The Crying Girl or Megan Fox’s well glossed lips, pouting in the mirror as glassy tears threaten to spill from her eyes in Jennifer’s Body - sadness is sexy. 

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But who’s tragic heroine are we? Rodrigo suggests that there’s a specific kind of painful expectation driven by the male gaze and patriarchy for hotness at all times that we’re sick of, determined to fight against. Back in 2014, however, artist Audrey Wollen coined the term “sad girl theory”, positing female suffering as an act of resistance. Like Rodrigo, she claws against claustrophobic emotional placidity to seek something raw, something real. Unlike Rodrigo, sadness becomes a route out of these confines, rather than the very structure that upholds them. 

“Seen on the feeds of It Girls like Bella Hadid, the crying selfie positions itself as a disruptive form of online authenticity.”

Seen on the feeds of It Girls like Bella Hadid, the crying selfie positions itself as a disruptive form of online authenticity. Much like Wollen’s view of female sadness and patriarchy, cry-posters often view the practice as being in protest to the overly curated highlight reel of social media. The reality, though, is that everything online, much like real life, is performance. In a world where there is no such thing as authenticity, who among us is really posting our truest of cries? Our snotty, puffy eyed, crumbs-in-the-bed wails? 

In a recent Substack post, artist Molly Soda recounts her own crying content on the internet - now a decade old. There’s a marked difference between her near three minute video, sobbing to Death Cab For Cutie, mascara streaming down her cheeks, and the photo dumps we see today but, in spirit, they remain along the same vein. Soda, in an earlier internet and as an artist fascinated by the online sphere, is markedly more frantic, aw, but nonetheless, also concerned with notions of hotness. As Soda puts it: “This scepticism of (mostly) girls documenting their sadness feels emblematic of our approach to how we view being online in the first place. Is it real, is it fake, is it attention-seeking? Who cares? Authenticity is an aesthetic, and I’d like to think we are all aware by now that we’re posting for attention, no matter the content.”

Whilst we may not all have posted sexy tears on main, most of us are guilty of taking the occasional pic for the group chat, or even so much as looking in the mirror as we cry - the post-weep glow is now considered as a near-universal truth. According to social media, crying make-up is in. It’s not exactly sinister but, equally, neither this or the crying selfie are the liberating forces of authenticity they pedal themselves to be.

None of this is to say that vulnerability is not a worthy cause. Embracing our feelings, whether it’s through a softness toward ourselves or indulging in some form of unhinged, borderline feral, display of emotion, is a valid pursuit. As our own voyeur or otherwise, it is, admittedly, sort of entertaining. Who are any of us to deny ourselves the pleasure of looking or, more importantly, feeling a bit sexy when we’re crying? 

In researching this phenomena, I stumbled across this TikTok that exemplified the point near-perfectly. The creator cuts the audio off, ironically just before Rodrigo’s frustrations around crying rear their head. “I’m grateful all the time” she lip-syncs, describing her catching a glimpse of her “long lashes, full lips, and rosy cheeks from crying”. She doesn’t, like Rodrigo, fight back at the suggestion of hotness, rather plays right into the eyes of her internal voyeur. 

The sad girl will always be entangled in a twisted fantasy of beauty, but what remains to be questioned is the limitations it places on our self-perception. Looking pretty when we cry may, upon first glance, make us feel better about our tears, but it also does little more than function as a convenient distraction. In media and art, it can feel like the real, raw humanity of girlhood is granted the capacity for value or meaning - like they’re finally taking us seriously. What the digital space does, however, is blur the boundaries between art and reality in our own lives. 

Through the crying selfie, we become the muse, misguidedly believing in our own depth whilst simultaneously denying it. Our emotions are emptied out and flattened to become just another signifier of a certain kind of girlhood; sensitivity and softness become plump lips and glassy eyes. It’s not a sin to indulge, to wish to feel beautiful and celebrate the moments that we do, but it is vital that we question why. The sad girl trope is perhaps something that will never go out of style but, ultimately, it reinforces the cruel notion that, under the male gaze, nothing really matters, as long as we look hot whilst we’re doing it.

Words: Alice Brown