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Do I Want Kids? Part 1: Mental Health

Kate Sloan

Am I too crazy to have kids?

This question haunts me. I’m embarrassed at how often it flits through my head. When I get sucked down into the whirlpool of depression or anxiety, those moods pose a question which only serves to perpetuate them: Are you too fucked-up to ever get the things you want? And of course, in the throes of sadness and fear, “yes” is the only answer I can fathom.

There are times when my mental health is so bad that I can barely take care of myself – food, sleep, hygiene – so it’s scary to imagine trying to take care of someone else at those times. How can you be responsible for another human being if you’re crying too hard to get up off the floor, or if the world beyond your bed feels too scary to contemplate?

I’ve heard many a horror story from people whose parents raised them in a maelstrom of mental illness. Children of the severely depressed can be neglected; children of the deeply anxious can absorb compulsive fears; children of people with personality disorders can grow up hurt and confused, unable to truly trust anyone. Of course, these stories aren’t universal, and I probably know just as many people whose parents struggled with mental illness and who nonetheless turned out fine, but it’s hard to tune out these narratives when you’re scared they could come true for you.

I’d like to think my co-parent would be a relatively sane, grounded person, to help balance me out. (As much as I admire folks who raise kids solo, that doesn’t seem emotionally or financially tenable for me.) But then you risk creating an off-kilter family dynamic where one person is over-relied upon to prop up everyone else, psychologically and logistically, and that’s not fair at all. Maybe this is an area where polyamory could be an advantage: a solid support network of de facto other parents could take some pressure off. They do say it takes a village to raise a child, after all. The results of a legal paternity test can tell you a lot, but they’re not the whole picture, and a parent or guardian obviously doesn’t have to be genetically or legally related to a kid to assist in raising that kid.

Even supposing that I could overcome my own craziness enough to take care of a child – and/or rely on the help of other, steadier humans – I would still worry about transmitting that craziness to my kid. Some varieties of DNA test can predict whether a person might develop certain mental illnesses, but even if I went the adoption route, I’d still be concerned my negative thought patterns and tendency to overreact to emotional stimuli would get passed on to my little one through sheer osmosis. I would have to be careful and deliberate in the ways I chose to behave around them, and the values and habits I let them pick up – though I suppose that’s true for any parent. You probably want to clean up your act around someone you’re raising, to some extent, whether by quitting smoking or cutting back on profane language or, yes, consciously dialling back your “crazy” behaviors if you can. Hell, doing this might even help me feel less crazy, too.

That said, I don’t think it’s all bad for a mentally ill person to raise a child. Hell, both my parents struggle with depression and anxiety, and if anything, it just made them more empathetic when I started to notice my own psychological symptoms. I’ve also learned about cognitive-behavioral therapy and dialectical behavior therapy while getting treated for my mental illnesses, and these are useful frameworks for anyone seeking to moderate and process their feelings. I could teach these systems to my kid(s), and maybe then they would have an easier time with childhood’s classically outsized emotions, like sadness, rage, and restlessness. Increased emotional literacy is one of the major silver linings I’ve found in my struggles with depression and anxiety, so I may as well try to impart it on my spawn.

It’s also worth noting that depression and anxiety don’t necessarily preclude you from being loving and supportive; you may just show your love and support in different ways than a neurotypical person, depending on how your symptoms manifest. I can still be there for loved ones when I’m having a rough time. It definitely looks different than my emotional support does when I’m feeling better – there’s fewer words of wisdom and more sitting in silence and solidarity – but it’s still a form of love. As the brilliant Carly Boyce pointed out in a suicide intervention workshop of hers that I attended, sometimes a person in distress doesn’t need you to pull them out of that distress – they just need you to keep them company until the feeling passes. As someone well-versed in distress, I could certainly do that for my kid.

So, am I too crazy to have kids? I don’t know. I don’t think it’s off the table entirely. I think, in order to feel comfortable taking that step, I would first have to feel stable in my medication regimen, brush up on my CBT and DBT skills, and have a relatively settled, dependable social support structure. But once those things were in place, I might just become a hyper-empathetic – if chronically frazzled – mom.

 

This 3-part series on parenthood was generously sponsored by the folks at TestMeDNA.com. As always, all writing and opinions are my own.

How I Became a Full-Time Sex Writer

Kate Sloan

Friends, this blog is SEVEN YEARS OLD today, and that feels absolutely wild to me. I was not always the delightfully busy, proverbial-phone-ringing-off-the-hook sex writer you see before you. Even people who seem like they sorta “have their lives together” had to start somewhere. I’ve read my hero Alexandra Franzen’s post “A chronology of my life as a professional writer” many times seeking answers and comfort, at times when it seemed like the writer thing just wasn’t going to work out… and so it feels like good scribe karma for me to explain, in a similar fashion, how I got to where I am now. As the youths are saying on Twitter nowadays: Buckle up.

2000 or thereabouts. I am a voracious bookworm, a semi-closeted nerd, a precocious weirdo at age 8. I spend hours chronicling my days in my Little Mermaid journal – and, secretly, penning erotica in my ornate Anne of Green Gables journal. Later, I will rip all the filthiest pages out in a bout of shame – but for now, the anatomically ill-informed trysts on those pages fill me with joy.

2006. I’m knee-deep in a musical theatre obsession, and believe, genuinely believe, I will be a Broadway performer someday. I devour all the books I can find on the subject – Audition, Making It on Broadway – and go to voice lessons and memorize monologues and make lists of my dream roles. One night, at a family party, during a discussion of all the kids’ various ambitions, my wise older cousin turns to me and says, “I think Kate will grow up to be a writer.” I laugh, because she’s wrong: clearly I’m going to be singing and dancing on Manhattan stages instead. Right?

2009. My (hot, British) English teacher pulls me out of science class to tell me my recent essay for him was exemplary and that he wants to use it in future lessons. My glee cannot be quantified. That same year, I win first prize in a student poetry contest, and I get to read my extremely gay poem onstage in front of a bunch of literary types. They give me a $100 bookstore gift card which I promptly spend on a lot of Bukowski.

2010. I take a Writer’s Craft class where I get to explore various different forms, ranging from Shakespearian verse to sitcom scripts. Later, one of my favorite teachers lets me take a one-on-one literature/creative writing class with her, tailored to my tastes and goals as a reader and a writer. She assigns me twisted fairytales, feminist essays, Angels in America. I write a play about romance, non-monogamy, and gender confusion, and they do a staged reading of it at my school’s Fringe Festival. I cry a lot in the aftermath, having heard my words in other people’s voices and been utterly lit up by it.

2011. That same teacher recommends me to Shameless magazine as someone they should profile, and they do. It’s my first appearance in a magazine, albeit not a byline. The article captures my frazzled artistic life at the time: improv, painting, poetry. I’m still not settled on the “writer” identity, though I’m getting there.

Early 2012. I take a year off between high school and university, trying to figure out what the hell I want to study. One night, at my commencement, I’m mesmerized by the ASL interpreter onstage, and ponder whether I should go to school for ASL translation, something I’ve often idly thought I might enjoy. But then I realize it would probably be best if I studied something I already know I enjoy and am good at… like… writing. Something clicks. I race home that night and write in my notebook: “MAYBE I SHOULD GO TO JOURNALISM SCHOOL??”

March 2012. I apply to a shitty retail job at a sex shop. I do some Googling about sex toys to make sure I know my shit incase they call me in for an interview – but they don’t. However, in the process, I discover sex toy reviewers like Epiphora and Lilly, and I think, “Hey, I could do that.” I start a Tumblr-hosted blog. I name it Girly Juice. “Could be a fun summer project,” I note in my journal.

April 2012. The owner of a website called Sex Toys Canada reaches out to inquire about a partnership. I’m still new to the sex toy reviewing game, so I eagerly negotiate a deal whereby I will get $140 in store credit each month in exchange for writing 2 articles for the company blog. I acquire my first “free” toys, including an Eroscillator, and feel like a business genius. (Over a year later, I will renegotiate and get them to start paying me in actual money. Only $50 an article, but still.)

September 2012. I start classes at Ryerson University’s School of Journalism. It’s hard – especially “streeters,” where you have to interview random people on the street for a story, the bane of my socially anxious existence – but I feel invigorated and inspired by the smart writers who surround me and the wonderful work I get to read every day.

2013. I get an unpaid internship writing and editing articles for a dating newsletter aimed at middle-aged women. A recommendation letter from my supervisor at the end of the summer says that I have “excellent written and verbal communication skills, [am] extremely organized, can work independently, and [am] able to effectively multi-task to ensure that all projects are completed in a timely manner.” I try to parlay the internship into a paying position, but they don’t go for it – probably, in retrospect, because their economic model hinged on not needing to pay people like me.

2014. I’m invited to write some pieces for on-campus publications, the Eyeopener and the Ryerson Folio; far from limiting me, my sex “beat” just makes people think of me first when they need a sex story written. A J-school colleague of mine interviews me for a story she’s writing for Herizons magazine about labiaplasty. In seeking out the mag so I can read the story, I realize they’d be a great fit for lots of the stuff I like to write about. I pitch the editor a feature story about toxic sex toys, and she loves it. My friends and family rejoice supportively about my magazine debut, a heavily-reported story called “The Greening of Sex Toys.”

2015. I attend a sex bloggers’ retreat called #DildoHoliday, and teach a workshop on generating content ideas and staying on task, since I am, according to one of the retreat organizers, “the queen of productivity.” Throughout the year, I’m interviewed for the University of Toronto campus newspaper, the Offleash podcast, Kinkly’s Sex Blogger of the Month feature, and Sex City Radio. Everyone seems suddenly interested in this weird sex writer girl.

Early 2016. I do my final-semester internship at the Plaid Zebra, where they let me write about sexual health, social psychology, and dick tuxedos. It gives me a taste of what it might be like to be a full-time staffer at a publication – and I discover that I think I’d rather freelance. I take a gig writing monthly articles for a sex toy shop’s blog, to supplement my growing income from blogging and journalism.

July 2016. I pitch an essay to the Establishment about dating faux-feminist men. They accept it, I write it, and… it goes viral. For several days, I basically cower in my bed, overwhelmed by the onslaught of tweets and trolls and threats. I wonder, many times, if the sex-writer life is really for me. I conclude that it is.

Early 2017. I work a sex toy retail job, briefly, before they fire me for no real reason. At first I panic about how I’m going to make ends meet, but then somehow the sponsored post requests and freelance story assignments pour in at exactly the right moment. The sex and relationships editor of Glamour reaches out via DM to say she loves my blog and would welcome any story pitches from me. I write for her – and Teen Vogue, and the Establishment, and Daily Xtra. I dutifully update my portfolio every time a new piece goes up. The Daily Mail writes about what a slut I am, and I’m terrified it’ll incite the trolls again, but it doesn’t, not really.

June 2017. I start my new dayjob as a social media writer for a firm that works with adult-industry clients. It’s 10-15 hours of solitary, largely self-directed work per week. The steady work allows me to relax and not worry so much about whether my more creative work will be able to support me. I stop shopping for button-downs and pencil skirts in a gesture of supplication to some future office-job self; I accept that maybe I am just A Person Who Works From Home Now, and that therefore it’s okay for me to buy star-print leggings and sparkly T-shirts instead.

Early 2018. A Spanish newspaper calls me “the Canadian Bridget Jones.” At my boyfriend’s urging, I pitch a story to a dream publication of mine, Cosmo, and they say yes. When it goes up, my perfect brother tweets, “My sister is now a Cosmopolitan-featured writer!” and I don’t quite believe it until I see his words.

Late 2018. I win an award from the Association of LGBT Journalists. I get nominated for Best Blogger in NOW magazine’s Readers’ Choice Awards. I write big meaty reported pieces for The Walrus and an op-ed for Herizons. I sell several sponsored posts a month, and do odd jobs copywriting and ghostwriting for various sex shops, dating sites, porn sites, and adult content creators. I do my best to follow Alex Franzen’s advice: underpromise and overdeliver. Then I’m invited to teach a sex writing class at the Naked Heart Festival and it validates me, affirms me. This is really my career. Wow.

2019. Herizons offers me a column; I accept. I do more copywriting and ghostwriting and social media writing. I pitch, and write, and network, and brainstorm. The sex writer life, to my delight, goes on.

 

Big takeaways, if I had to choose a few:

  1. Even if your heart is in a particular genre of writing, consider branching out into other areas. I wouldn’t be able to do my fun, creative blogging and essay-writing if it wasn’t supported at least some of the time by social media work, promotional copywriting, etc. – not to mention, going outside your comfort zone helps stretch your creative muscles.
  2. Pitch, pitch, pitch, and pitch some more. Pitch publications you would love to write for, not just ones you think would “let you” write for them. Aim high!
  3. Getting paid for your writing – particularly blogging – can be a slow, long haul. Don’t expect anything to happen overnight. It is more than okay to supplement your income with a dayjob along the way, and even once you become more established. We all gotta eat.
  4. Trolls, h8erz, and rejection letters from editors can all feel much bigger and more important than compliments, fan letters, accolades, and achievements – but they’re not. Do your best to let setbacks fade into your history; they don’t have to define you, as a writer or as a person.

Thanks for being here! It’s been a pleasure spending seven years with you – or however long you’ve been around. ❤️

Obsessed & Distressed: Reflections on Rabid Love

Kate Sloan

I learned what love felt like from someone I couldn’t bring myself to love.

She was a close friend in high school whose harmless puppy-love toward me darkened into something deeper over our sophomore year. Try as I might, and try though I did, I couldn’t conjure the caliber of crush in return that she shone on me like fervent floodlights. Love can’t be forced, and she knew that, but I’m sure it made her sad anyway. I’m sure it also made her sad that we had a sexual relationship for over a year that remained only one-sidedly romantic. Look, tenth-graders don’t always make the most rational decisions.

I’ve spent ten years processing that relationship, and I guess she probably has too. We’ve made amends for the ways we fucked up, each trying to squeeze the other into an ill-fitting box. But what’s stuck with me most from that relationship was how obsessed with me she was.

(A note worth noting: this post will throw around the words “obsessed” and “obsessive” in their colloquial senses, and not the sense used in mental health diagnostics – although I and at least some of the people I’m describing have mental illnesses that feature some degree of invasive thought-loops one could consider obsessions.)

My tenth-grade paramour wrote me long emails and romantic poems. She kept up with my foibles on Facebook and Twitter, both relatively new and uncommonly-adopted technologies at that time. She mined me for minute trivia, plumbing my lore like I was my own cinematic universe. After a while, she knew everything from my favorite flavors of ice cream to my top 5 favorite Regina Spektor songs to my darkest fears. When our English teacher gave our class carte blanche to do a deep-dive on a topic of our choosing for our final project, she did her project on… me. Those documents are still tucked away in my Google Drive somewhere, curious little remnants of a love that once was.

It is, of course, flattering to be someone’s top priority and main focus – assuming this attention doesn’t frighten you or make you uncomfortable. But I think the reason her love comforted me was that it felt familiar. My crushes had always taken on a similarly obsessive tone: when I pined over pseudo-celebrities of the local comedy or theatre scene, I Googled them late into the night, memorized their answers to interview questions, gave them more real estate in my brain than perhaps they deserved. So when I felt that similarly laser-focused love being aimed at me, I recognized it for the love that it was. Though she was the first person ever to fall in love with me, it wasn’t hard for me to believe or accept; I knew what it was because it looked how I expected it to look. It looked like how I would love someone, if I ever did.

Almost a decade later, the shadow of that old love filtered through my consciousness again – because I fell in love with someone who wasn’t obsessed with me. And it hurt.

I wonder, in retrospect, if I was drawn to him because he was everything I’ve never been able to be: chill, cool, aloof. Aside from initiating our relationship by asking me out on Twitter, his expressions of enthusiasm toward me were scant. Maybe that just made me want him more. (Is this a lesson we all have to learn at some point? That the chase is fun but also exhausting? I hope I’m done learning that one.)

I felt – to partly dilute a word that maybe I shouldn’t be diluting – gaslighted. He told me over and over again that he liked me, loved me, wanted to be with me, but his behavior was comparatively devoid of evidence he wanted me around. He’d ignore my texts for hours at a time, neglect to keep his promises, back out of plans at the last minute, and pull away coldly when I wanted closeness and warmth. I don’t know that he was doing this intentionally, as the “gaslighting” label would suggest – but the net effect was, regardless, a sense of emotional whiplash. I kept reminding myself to listen to his words, because they no doubt were truer than my anxiety-warped perception of his actions – but actions, as you well know, tend to speak louder. His were drowning out his words.

I brought this to his attention only once, and came to regret it. We were looping the same argument we’d been having for basically our entire relationship: I resented that he wouldn’t give me the assurances I felt I needed, and he resented that I needed them. Grasping at straws, I tried to explain: “It’s hard for me to recognize love as love when the person isn’t kind of obsessed with me, because when I like someone, I want to know everything about them, I want to see them as much as possible, and I think about them almost all the time.”

Some part of me hoped he would counter with what I wanted to hear: that he did think about me constantly, that he was obsessed with me; how could I not have noticed? Instead, he replied, “I don’t really get obsessed with people. I never have. That’s just not how I operate.”

Wise and level-headed people in my life, like my therapist and my best friend, would probably tell me to just accept a lower level of attention and devotion from partners. Just because someone doesn’t pine over you nonstop, they might tell me, doesn’t mean they’re blasé about you. If you broaden your view of what love can look like, you expand your ability to be loved, to feel loved.

That’s true, I guess. But I wanted love I didn’t have to do cognitive backflips to understand. I wanted love that was more joy, less compromise. I wanted love that mirrored my own, that matched me in my wild zeal. So when that boy broke up with me, although I was crushed, part of me was relieved. It felt more peaceful, more pleasant, to know for sure that no one loved me romantically, than to beg for scraps of affection that never quite felt like enough.

When I met my now-boyfriend, then-Twitter-crush, one of the first things he told me about himself is that he’s obsessive. I thrilled at the possibility of familiarity.

It didn’t take long for me to discover how right he was, how core this quality is to who he is. Intrepid Googling and curious research have left him well-informed on a broad range of topics. He can tell you the top 5 best cocktail bars in any neighborhood in New York, off the top of his head. He geeks out about etymology, psychology, philosophy. Once, during a conversation over drinks about whether or not our D/s dynamic is technically 24/7, he said, “That reminds me of this quote from SM 101…” and pulled it up on his phone in seconds. I swooned.

As we got to know each other, he’d casually reference old videos of mine, tweets, blog posts. He got embarrassed each time I called him out on it, backpedaling and blushing audibly over the phone, but my screeches of “How do you know that?!” were never accusatory – only excited. For me, combing through a crush’s internet presence is par for the course; it had been years since anyone had made me feel spotlighted that way in return.

He commissioned me a custom perfume based on a list of preferences he cobbled together from research. He devoured my sex toy reviews so he’d know what I like to be fucked with, and worked his way through my podcast so he’d know how I like to be fucked. When he sends me flowers or brings me treats, his selections are educated guesses – or sometimes, exactly the right thing.

The more I think about it, the more I doubt that “obsessive” is the right word. The essence of romance, and indeed of love, is focusing on your paramour: giving them your attention, putting effort into them, demonstrating your enthusiasm for them over and over. That sharp passion is what was missing from so many of my past relationships, which is why it feels especially good in this latest one. I spent years making desperate excuses for aloof partners, twisting their apathy until it looked like love. I settled over and over for paltry affection that barely warmed my skin, let alone my insides. I gave up on thinking of myself as someone worthy of obsession, even as I continued to furtively memorize my crushes’ likes and dislikes by the dim glow of my laptop in the dead of night.

I’m so happy now to be loved in the way I’ve always craved, and so happy to have discovered that love doesn’t have to be a compromise at its core. Sometimes it can just be exactly what you want.

Love Through a Voyeuristic Lens

Kate Sloan

In the age of the internet, it’s normal for our private lives to play out in public. In just a few clicks, you can peek into a beauty influencer’s medicine cabinet, peruse a sex toy blogger’s prized collection (hi), or visit voyeur house private cams where you can watch the life of real people. Not everyone is thrilled about all this openness and exhibitionism, but it’s undeniably part of our culture now.

So, as a sex writer and certifiable member of the Oversharers Club, it surprised me how private I was about my current relationship in its infancy. I talked about it in oblique terms on Twitter, and mentioned to a few friends that I’d been texting with a promising new dude who lived in New York, but for the most part, I wanted to hold those cards close to my chest. Our courtship happened primarily late at night via FaceTime and iMessage, encrypted end-to-end, cordoned off from the rest of our lives. It felt weird to bring it out into the open by talking about it too much – like someone throwing open the door of a darkened closet during a heated game of Seven Minutes in Heaven.

But because this private intimacy was shared between only me and my new crush, it felt almost like it didn’t really exist – like it could be a mirage, a hallucination, a midnight fever-dream. It brought me back to my early days on the internet, when I’d build elaborate romances with strangers in IRC chats and then just go to school the next day like nothing had happened, like nothing had changed. Even as we escalated to using weightier words for each other – partner, boyfriend and girlfriend – still, part of me felt like: here is my “real life,” and here is this relationship, and scarcely the twain shall meet.

So it was quite a jolt the first time my new love – mb – came to visit me in Toronto. Seeing him in familiar locales, like my bedroom, my parents’ living room, and the coffee shop I go to every week, was as jarring as a bad green-screen sequence in a low-budget movie. How could such a cute, sweet person, who had taken on an almost mythical quality in my mind, exist in the world at all, let alone in my life? I felt like Rob Gordon, the antihero of High Fidelity, when he looks up his long-lost college girlfriend: “She’s in the fucking phone book! She should be living on Neptune. She’s an extraterrestrial, a ghost, a myth, not a person in a phone book!”

He met my family. He met my friends. I took him to my birthday party. But none of it quite felt real – until, shortly after leaving the party, I got a text from my friend Suz, who had left at the same time as us. “Okay, so, creepiest thing I have ever done,” she wrote, “but when we departed at the subway, I could see y’all from the other side. You both looked so in love, so I took some creepy stealth pics for you.”

mb and I giggled over the photos, crowing “We’re so cute!” and zooming in to examine our amorous body language. Something clicked. Seeing my relationship from the outside allowed me to believe in it from the inside. I felt validated: Yes, he really exists; yes, he really is that cute; yes, he really loves me! Some part of me had been continually nervous that he would evaporate somehow, that I would wake up from the dream or forget to save my game, and he would be gone. But there he was, in a handful of .jpegs, flirting with me on a Toronto subway platform, irrefutable.

Feeling observed in a feeling can make that feeling all the more palpable. Maggie Nelson writes about it in Bluets: “We sometimes weep in front of a mirror not to inflame self-pity, but because we want to feel witnessed in our despair.” Beauty vloggers know this, as do reality TV stars, theatre actors, Instagram influencers, exhibitionists and voyeurs. Like Schrodinger’s cat, sometimes it is the very act of seeing that heralds the seen object into existence. My relationship would have been real with or without spectators, of course – but my rock-solid, comfortable, life-affirming belief in that relationship? Maybe not so much.

 

This post was sponsored. As always, all writing and opinions are my own. Thank you to Suz for the photos; we love them!

Date Diaries: Towers, Oysters, & Amorous Nights

Kate Sloan

Hi! Welcome to something new I’m trying, Date Diaries, a feature where I’ll write about dates I go on. I’m revisiting a week I spent with my partner in Toronto back in December, for our first anniversary…

On mb’s first night back in town, I went to meet him at the airport, which has become a tradition for us. We have a protocol whereby I have to ask him, prior to his takeoff, what he’d like me to bring him at the airport – food, gum, coffee, whatever – and then meet him in the arrivals area. It’s exciting, getting to see him at the earliest possible moment, rather than waiting for him to Uber to my apartment like I used to.

On this day – December 12th – I subwayed across town to Pearson Airport in the west end from a psychiatrist appointment in the east end, trying to read my Kindle on the train but failing because I was too excited to concentrate. Once we found each other in arrivals, we took a car back to my place, ~reconnected~ with some sex-‘n’-kink, and then were faced with the question of where to go for dinner.

This always happens. Usually he gets in late, because air travel is a chaotic nightmare, and by the time we’re settled and ready to eat, many restaurants have closed their kitchens. So it’s become a tradition of sorts for us to go to Bar Isabel on those first Toronto nights, because their kitchen is open until at least midnight (bless them, bless them all). It’s one of the best-reviewed restaurants in the city, and for good reason: the ambiance is chill and romantic, the tapas-style menu is impeccable, the cocktails are swell, and the servers are top-notch.

As the clock ticked over to 12:00AM of the next day – December 13th, our anniversary – I tweeted about how happy I was to have spent a year with such a wonderful person, and we toasted to our relationship, our love, and our future. Aww.

What I wore: I was feeling romantic so I put on the dress I was wearing the day that we met, one year previous. It’s a black and red floral-print fit-and-flare dress I got at H&M god knows how many years ago. I also wore my collar, of course.

What we ordered: We usually get the punch when we go to Bar Isabel; I think this time we got the “fancy punch,” which contains liquors, citruses, teas, herbs, and bubbly wine (they change up the specific ingredients on a night-to-night basis), because we were celebrating! We ate oysters, bread, manchego cheese, shishito peppers, and grilled octopus. Divine.

My boyf is an over-the-top romantic, making him a good match for someone like me who is sentimental as fuck and also likes to write about dates she goes on (hiii). For our anniversary, he surprised me by taking me to one of the fanciest and most tourist-y places you can go for dinner in Toronto: the 360 Restaurant at the top of the CN Tower. As we were walking to the elevator that would take us up to the restaurant, we were bustled into a photography area where they snapped some cheesy pictures of us in front of a green screen – hence the adorable watermarked monstrosity you see above.

The whole conceit of the 360 Restaurant is that you get the best possible view of Toronto, and the entire restaurant rotates slowly, so you get to see all the way around over the course of your meal. I hadn’t been up there since my mom took me to an opening-night party for The Lion King back when she was working as an entertainment reporter more than a decade ago, so it was cool to go back, especially with someone I love so much.

After dinner, we checked out the famous glass floor and then cabbed to Civil Liberties for a nightcap before heading home. Ideal date night!

What I wore: Sir told me weeks beforehand that if I planned on buying a new dress for our anniversary, he wanted it to be blue and shiny/sparkly in some way – which, honestly, knowing me, it would’ve been anyway. I trawled the local mall all day, trying on several unsatisfactory contenders, before finally landing on this $17 pale blue velvet spaghetti-strap dress from Forever 21. I wore it with black tights, my collar, a black cashmere cardigan, and the gorgeous blue Coach bag mb had just given me as an anniversary gift. The suit he’s wearing, by the way, is the same one he wore on our second date; aww.

What we ordered: We split a dozen oysters and I thiiink I had roasted salmon with risotto on the side. And, as per usual, we drank excellent cocktails, though I can’t remember what they were. I was pretty focused on the cute boy across the table from me!

Sir introduced me to La Banane and it’s become one of our favorite Toronto dinner spots. The food and service are both absolutely incredible. I feel like a queen every time we go here.

After dinner, we rounded out our evening by going to see Hook-Up at the Bad Dog Theatre (their hilarious and often quite romantic runaway hit) and stopping by Civil Liberties again for more cocktails. Three of our very favorite things in one night – amazing!

What I wore: This dress is one of Sir’s faves in my wardrobe so he chose it for our fancy night out; it’s a form-fitting, low-cut, navy velvet dress with an asymmetric hem. I bought it at Forever 21 when I briefly had a sugar daddy, envisioning wearing it on elegant dates with him, though that plan never came to pass! This time I paired it with black tights, a black cashmere cardigan, my collar, and my new Coach bag again.

What we ordered: Our appetizers were oysters again (we’re so predictable) and seared foie gras with hazelnuts and a little cup of wine on the side. I had their duck breast entrée (soooo tender and good) and Sir had the Eurobass. My fave cocktail here is the Penicillin; I don’t normally like smoky Scotch but this drink blends it with lemon, ginger, and honey, making it much more palatable. Toward the end of the meal, the restaurant staff had to re-seat us to make room for a big group that was coming in, and they sent over two glasses of amaro on the house for our trouble (my first time ever trying amaro!). Sooo fuckin’ classy.

Been on any date you’ve especially loved lately?