Dissecting the Heartfelt and Humorous with Caitlin Andrews

Caitlin Andrews (she/her) is a writer, editor, social media peruser, and undergraduate student who lives in Scotland, but doesn’t really have the perks of a fun accent. She has been previously published in a variety of independent and corporate publications, including Soft Sound Press, Unpublished Magazine, MovieWeb, and most recently Periphery Magazine, where she holds the position of Senior & Managing Editor. 

Cait’s favorite hobbies include reading, writing, dying her hair, smoking cigarettes, quitting cigarettes, bullying her neighbors on the internet, yelling into the sky, debating a legal name change for memorability purposes, and routinely being a smart-ass. Wherever she’s going, it’s probably hell. 

O: When did you begin writing? 

Caitlin Andrews: You know, my nursery wouldn’t let me graduate without knowing my ABCs, so I think it was probably sometime around then. In terms of properly writing, I’d always been an imaginative kid—I vividly remember spending weekends wandering around the Scottish hillside wearing a variety of neurotic-mother-mandated sunscreening hats, and chatting the ear off my parents about the imaginary universes I had created in my brain. None of them were any good (in fact, the first attempt at a novel I wrote aged eight was a blatant knockoff of Harry Potter, starring a little witch girl named Lily Potts), but I was a hyper-anxious child and, at the time, fiction was a great way to obtain some control over being a kid, in attempts of forgetting how much it sucked—a feat I’m still trying to achieve, even now. 

In terms of trying to be halfway funny: when I was nine-ish, we went on a school trip to this activity bunkhouse thing called Comrie Croft (which, for the record, contained far too much hillwalking for a bunch of grouchy middle-class children), and when we got home and were asked to write a short essay about our experiences, I remember thinking about it for a few moments, before writing an opening line where I described myself as a “twat in a beanie hat.” I don’t know if I fully registered “twat” as being a bad word (one of the many consequences of growing up in a house with an Ulsterman and an Australian), but I remember thinking, even if unconsciously, that even a feeble attempt at “being funny” was one of those things I could do to take control over an otherwise unappealing life. Much of this realisation had been prompted by the reality that my beautiful best friend had spent our week away kissing good-looking boys and sneaking off in the middle of the night to play games of Truth or Dare, but I had short hair, and was greasy, and wore stupid cagoules in a time when you were still allowed to hurl abuses at the people you thought were lesbians, so trying to shift my competition a little bit seemed natural; to channel into the energy of, “This is something you can be a bit of a dog while doing, and still succeed! People might like you!”

As for when I began writing well…let me know when it happens, will you?

O: Is there a writer that you look up to, whether it be someone who motivated you to begin writing or someone whose work inspires you today? 

Caitlin Andrews: In terms of recent inspiration, I think Cynthia Heimel, Chuck Klosterman, and Merrill Markoe have probably already influenced my writing to a certain extent. I had a very temporary position at a small magazine as a Sex and Intimacy writer earlier in the year, and during the course of my various internet travels, stumbled across a copy of Sex Tips for Girls by Heimel, which really reinvigorated my passion for both reading and writing (and, much to my gratitude, reminded me that not every book has to be painfully serious). Honestly, prior to that, I hadn’t really read a book in months—there’s something about spending thirteen years in school that can suck the extra-curricular enthusiasm right out of you, but now that I’ve started on this Goodreads Book Challenge of 25 books a year, I’m burning right through them! It’s just about learning what you want to read and, in comparison, the shit you feel like you’re obligated to want to read.

O: If you had to describe your work in three words, what would they be and why? 

Caitlin Andrews: Hmm, I think that probably depends on my target audience—if my very professional grandfather asked me to describe what I wrote about online, words like “raunchy” probably wouldn’t spring to mind so quickly. But, if I had to pick an easy author tagline, I think I’d use words like “Crass, Lighthearted, and Humorous,” just to let people know the kind of content I like to put out into the universe, and that they should dip out for the foreseeable future if they don’t like naughty language.

On an actually vulnerable level, I’d like my work to be perceived as “Effortful, Honest, and Empathetic.” Maybe that’s incredibly self-aggrandizing, a trait my adolescent brain seems to struggle with shedding, but I think at my core, I just want to my work to have some effect on the two people that read it. To especially demonstrate to young women that you can be bad in bed, or have neuroses, or just generally be a bit unappealing to most of mankind and still have some semblance of a future. Life’s not finished just because you started in last place and you’ve spent the rest of the race running backwards; there’s always time to get past this thing of needing to be “the perfect woman” in every sexual or romantic experience (though admittedly, even though I say this, I do still have that recurring thought that whispers, “Yeah, but if someone I’m attracted to reads this, will they think I’m cool for saying it, or will they think I’m less sexy because I try not to care about being sexy?”). At the core of it, I want people to feel better than I do, and if I didn’t have some deep-seated need for connection and understanding, I’d probably be off chasing a desk job that might even pay me money.

O: What is your favorite part of the creative process? 

Caitlin Andrews: Probably not the drinking five cans of Redbull, convincing myself I’m having a heart attack, and then passing out over my laptop and sustaining a major neck injury, though it’s definitely nearing the top of the list. Also probably not convincing myself that I can Bukowski a good article by unsuccessfully trying to drink a bottle of spirit, because I’ll usually end up half-naked, on the floor, and crying about some vague childhood trauma with a blank Google document. 

I’d say the proper best bit is when you’ve taken a week or two away from writing, just long enough for you to start developing this kind of paranoia that you’ll never be able to write again, and then you sit down at your computer and it just flows. That moment when everything you’ve been thinking about recently just pours itself into words, and you can physically see your work shaping up into something not totally terrible. I wish I could bottle that feeling and drink it instead.

O: What is your favorite piece of work so far and why is it your favorite? (Please include a link if you have one, we’d love to include it on the website!) 

Caitlin Andrews: Honestly, my favourite piece of work probably doesn’t exist yet! I spend most of my time writing, editing, drafting, re-drafting, reviewing and then rewriting, but as soon as I make the decision to put a piece anywhere on the internet, I usually feel pretty gross about it. My ultimate goal is to make sure my oldest pieces are my worst, so I can guarantee I’ll feel as embarrassed as an adult about the pieces I write now as I do now about the pieces I wrote when I was fifteen!

But if I had to pick a favorite so far, I think I’d choose “Indiana Jones and The Case of the Apathetic Anal Sex,” mainly because it’s so utterly ridiculous and strange that I think it really reflects my harebrained nature. You don’t realize how jankily your mind bounces from topic to topic until you go from anal sex, to middle-aged divorcees, to Aquaman, to Indiana Jones, to McDonald’s fries, to the Riverside Museum and back again. Also, because if I had written this piece five years ago, it would have been a scandal.

O: Your writing reminds us a ton of Joan Didion—the language is precise, the feelings somehow raw and detached in the same breath—but it’s also so inherently you! Could you talk a bit about how you found your voice as a writer? 

Caitlin Andrews: Joan Didion? Wow! Careful, if you let my head get any bigger I won’t be able to fit through the door frame. Honestly, I think “finding your voice” is just one of those things that happens to you, like magically becoming a super genius at twenty-five when your brain is finished developing (or so I imagineI’m basing my theories off the assumption that having a fully cooked brain is like that novel writing scene from Limitless). At some point, you either get comfortable enough to fully immerse your personality into your writing, or you can, quite literally, die trying. I will say though, academia is a total fuckfest when it comes to writing stuff that actually appeals to people. You get conditioned into prioritising bibliographies and word counts and the exclusion of a first-person pronoun; worst of all expressing an individual opinion not originally presented in a textbook, which means, if you’re a person who has spent a lot of time recently in school or university, you’re probably going to be writing shit for a little while. 

For me personally, I wrote almost exclusively shit for several months. Every time I opened a Google Document, I crushed my personality into a little box and said, “Sit there, nobody cares about you right now,” while writing things that a chimp with a keyboard could replicate. Some of it was successful, and some of it was so totally terrible that I want to weep into my hands at the idea that it could ever be associated with my name, but that’s part of the big learning curve that is getting a bit less bad at something. You just have to keep writing things that suck, acknowledging that they suck, writing things that you don’t think suck, and then four months later realising that they do, in fact, suck. Now do you understand why my work is so vulgar? 

O: Your piece Unhappy Mother’s Day is a stunning and heartbreaking contemplation on familial relationships and what it means to value your own self-worth. How does your writing help you heal and connect with yourself and others?

Caitlin Andrews: That’s a good question, I’ve actually been thinking about this recently! So, as we know, I am as depressive as I am neurotic, and I spend most of my evenings devising cruel and unusual methods of psychologically torturing myself. After a hundred thousand hours’ worth of clinical trials, I’ve discovered that my own personal hell is letting my brain repeatedly poke at all my painful and embarrassing memories, whether it’s the mildly dumb stuff I did in the corner of a classroom aged twelve, or the incredibly dumb stuff I did in the corner of a bedroom aged sixteen (…truly, if we could inject teenagers with my inescapable sexual memories, it would be way more effective at preventing underage sex than abstinence education). However, the discovery of writing has also unearthed two things when it comes to my experience of healing from embarrassment and pain: the first being that I can now use these terrible memories as grist for the literary mill, and the second being the fact that I am embarrassed by some of these memories is actually more embarrassing than the event itself. 

For example—when I was a child, I went to swimming lessons every Tuesday night. During these lessons, I was expected to swim several laps to the end of the pool and back, while my mother read her book and looked down at me from a large windowed balcony. Around half of this time was spent with me choking on piss-and-chlorine filled pool water (which, if you believe the internet’s stance on cyanogen chloride, probably explains why I am constantly nauseated and lethargic) and trying not to pay attention to other kids’ manky plasters knocking about in the pool filter, until one day, I didn’t manage to complete my final lap. Instead, I swam to about the halfway line in the pool, kicked my legs like the seafaring dolphin I knew I could be, swallowed some more pool water and gleefully lifted my head, thinking I had already probably won the lap-race and was about to be crowned the next Michael Phelps in training. Instead, I found myself still in the middle of the pool and staring at the befuddled face of my swimming instructor and the other children, who had actually completed their laps. “You just turned around and did a spin in the middle of the pool,” my mother later announced, in a tone some might consider unmaternally gleeful. “We were all watching.” 

Cosmically, is that story actually that embarrassing? Not really. But did it haunt little childhood me, to the extent I might have just as well taken a poo in the pool and sucker punched little Jimmy in the next lane hard in his little wet face? Absolutely. I spent the next week trying to convince my mother to let me stop taking swimming lessons, which in practice lasted for about as long as it took to arrive at the community centre and get out of the car. I’d have earnestly preferred to drown than think about it. But now that I have the opportunity to divide my life into “publishable” and “unpublishable” content, that story wouldn’t even make the cut, because it’s just not that embarrassing, or really, that interesting. So, as it turns out, the best way to cope with pain and humiliation is by exploiting yourself on the internet. Who knew? (Other than the pals who predicted I’d end up doing porn, I mean.)

O: On a much lighter note, you’ve done a ton of fantastic work reviewing music and film. What about these two mediums is fascinating to you? (And if you have a favorite song/album/film, please do share those with us as well!)

Caitlin Andrews: Honestly, I consume a ton of internet-appointed “male manipulator” content (think: Tarantino, Scorsese, literally anything written by Bret Easton Ellis) and when you consider yourself a feminist, there’s a tiny voice in the back of your head that says, “Hmm, all of this is great, but I can’t freely enjoy it without acknowledging that if it’s got a cool male protagonist, there’s often a woman in the background having a really shit time.” It’s especially difficult to critically dissect a form of content when you find the protagonist attractive, or the production itself is aesthetically pleasing, and I often have to watch something a few times to analyse it beyond looking at the pretty people and pictures. So, I think that probably explains why I write so much content about film at least, because I’m capable of loving really good toxic shit, and I need to find a way to clear my hypocritical liberal conscience!

In terms of music, I’ve got absolutely no skills to actually critically analyse anything, given my lack of ability to play an instrument (other than maybe an E minor chord on guitar, which is about as impressive as it is complex), so I’ll usually just turn to tyrannically bullying the artists I love and hope that makes for interesting content. So far, that list has mostly just included Matty Healy, the poor bastard. But I think it’s important to note I don’t ever really write articles about stuff I’m apathetic towards, so when I do comment on a piece of content, it’s usually because I have some form of appreciation for it!

In terms of my favorite music at the moment, I’ll spill the beans on myself and drop you the first few songs in my On Repeat Spotify playlist: “Me & Mr Jones” by Amy Winehouse, “You Never Can Tell” by Chuck Berry, “Let’s Get It On” by Marvin Gaye, “I Can’t Stand The Rain” by Ann Peebles, “I Fall In Love Too Easily” by Chet Baker, and “I Wanna Get Next To You” by Rose Royce. I guess you could say there’s a theme there.”

O: At Periphery Magazine, you worked as a staff writer for two months before moving up to be their Senior & Managing Editor! Could you talk a bit about how you managed to move vertically within an organization and share any advice you might have for someone who aspires to do the same? 

Caitlin Andrews: Um, be obsessive as hell. For a few months, I just went ham with suggesting things and trying to develop projects, and when it looked like I could work with my lovely editors Katrina Kwok and Madison Case to help bring Periphery to a larger audience, I quit writing for other places in hopes of trying to make it succeed! I don’t subscribe to the idea of “hustle culture” by any means (in that I think you should be allowed to sleep, and watch Netflix, and eat food that doesn’t exclusively come out of a powder pouch without being labelled lazy) but there’s something to be said for picking what you want and earnestly working towards it. 

In terms of advice, I think if you want to move vertically, you just have to follow a few reasonable expectations: be polite, meet your deadlines, be receptive to communication and feedback, and if you’re looking to rise in a position quickly, go above and beyond to demonstrate your commitment to the publication wherever possible. Above all else, be effortful! Wherever you wind up, you’re never going to regret having tried to the best of your ability, and on a personal level, even if my writing career goes to shit, I like to think I’ll still have a collection of essays for my future kids to be embarrassed about.

O: If you could give new artists some advice from what you’ve learned, what would it be?

Caitlin Andrews: In my opinion, every single good piece you’re going to write is going to be vulnerable. Even if it’s humorous or tackles a serious topic in a light-hearted way, it’ll probably cut close to the bone for you emotionally when it’s released, which is why it’s important to start leaving the self-doubt at the door when you start creating whatever you want to create. For me, I get stuck thinking about all sorts of consequences when I write things – what will my mother think? Are some of my former classmates going to stumble across my sex articles from my LinkedIn profile and further solidify my reputation as, justified or otherwise, the class slut? If my current relationship ends, is this content something I’m comfortable with an asshole on Tinder turning into a pick-up line? It might not be possible to completely abandon those worries, but coming to terms with the fact that people probably won’t like you and that you need to be yourself anyway has been a powerful lesson for me, both in writing and in life. 

Also, this might be weird, but if you were a bullied kid, that’s your superpower. There’s no one more observant than a child hellbent on hurting your feelings, so analyse what people tried to kick the shit out of you for, and figure out what characteristic made you special. Cool people suffer, but really cool people turn that suffering into something.”

O: Do you have any upcoming projects that we should look out for? 

Caitlin Andrews: I’m so going to jinx this, but at the moment I’m trying to figure out the beginning stages of building a portfolio on Medium! Last night, I actually quit my freelance job at MovieWeb in hopes of pursuing some more diverse content (mostly of the sex and pop culture variety), which I’m really looking forward to sinking my teeth into over the next few months. There are also a few pieces I’ve nudged towards slightly larger publications, so fingers crossed for that!

Thank you so much to Caitlin for sitting down to chat with us so extensively about both life and work! You can check out more of her work on her website and find her also on LinkedIn and Medium!