the time i accidentally went on a date with a 40-year-old

I know what you’re thinking; how does one “accidentally” go on a date with a 40-year-old? Well, children, I’m about to tell you. So grab your popcorn and gather ’round while I spin this sordid tale…

(Side note: It wasn’t actually that sordid, a word which means, as defined by the dictionary, “involving ignoble actions and motives; arousing moral distaste and contempt” or “dirty or squalid,” depending on context; “sordid tale” just has a nice ring to it.)

Once upon a time, in the dimly lit interiors of one of Toronto’s premier vegan/vegetarian establishments, a tall, semi-good-looking man approached the cash register to order a hot chocolate and a cookie. His age was unclear, especially under the small pot lights that cast a strange orange glow upon the surroundings. He had one of those ambiguous faces that could have belonged to someone anywhere between the ages of 27 and 37.

Behind that cash register, as you can probably guess, was me; pink-haired, probably overdressed, emotionally exhausted from being verbally berated by Uber Eats drivers, and probably fantasizing about the bowl of chick’n tenders we’d try to sweet-talk the kitchen into making us later that night. I recognized the man; he came in fairly regularly, and he had an interesting name, which made it easier to remember. Plus, I’ve found that people are more inclined to tip if you remember their names. I greeted him with a smile of recognition.

“John*, right?” I said when it was time to punch in his name for his order. (*Names have been changed).

“Wow, you remembered!” he said as I ran his card.

“Well, I always remember people with interesting names,” I replied. “John is a really cool name.” I manoeuvred to the other end of the counter to get his cookie.

“And what’s your name?” he asked with a half-smile, walking parallel with me towards the desserts.

“I’m Sam,” I answered, ducking down to grab a paper cookie bag.

“Well, Sam, nice to meet you,” he said. “Hey, this is kind of a weird question, but are you by any chance an artist?”

I laughed. “Um, no, not really. I mean, I like to write, and I have a blog that I suck at posting on where I yell about feminism, but I don’t know if that counts.”

“I’d say that at least somewhat counts,” John replied. “You’re still creating something.”

“Why do you ask?” I handed him his cookie.

“Well, you just kind of look like an artist.”

Which, I mean, I won’t dispute that, with my pink hair, a septum piercing, baby bangs, cat-eye glasses, and bright lipstick. I’d probably think I had creative interests too if I saw me. Then again, I also just described at least 60-70% of Toronto’s female population between the ages of 18-30, so take that as you will. In any case, as someone whose desired aesthetic is “vaguely artsy Toronto hipster who unironically loves Panic! At the Disco,” I was quite pleased.

“I can give you my blog if you want to take a look…” I said hesitantly.

“Sure, that would be awesome,” he replied.

I wrote my blog URL on a piece of receipt paper, we exchanged parting pleasantries, and he went on his way.

I didn’t really put much stock into our interaction; after all, why would he care about the musings of some random restaurant cashier? But, lo and behold, a couple weeks later, I received an Instagram DM notification:

“Hi Sam, it’s John from the restaurant,” the message read. “I checked out your writing; interesting indeed. It’s fair to say, you’ve had some interesting dates. I’d love to hear more of your stories sometime. Glad to have found you on here!”

Butterflies in my stomach, I responded in kind. A real human person, who I’d met in real human life and not from swiping on an app, was interested in me (I mean, probably, because again, generally one doesn’t go around reading the blogs of strangers off the street without some kind of ulterior motive). An actual meet-cute! After a bit of back-and-forth, we agreed on a day to meet up for evening drinks.

The day arrived. I still wasn’t sure how old he was, and I was afraid to ask, but that seemed like a bridge for Future Sam to cross if it came to it. By all accounts, he was a massive step up from the last dude I’d gone on a date with, who, upon my arrival, informed me that he had longboarded to our lunchtime rendezvous at a pho restaurant (call me shallow, but longboarding is not an appropriate way to traverse the streets of Toronto, especially for someone over the age of 19. Please, just bike like a normal person).

From lurking his Instagram, I gathered that John was someone with a career. Someone who wore button-up shirts and decent pants every day. Someone who only donned beanies for warmth purposes and always styled them to cover his ears, rather than perched on top of his head like some kind of bizarre cranial condom. Someone who semi-regularly hung out with Derek from Life with Derek.

I’m sure you can understand my excitement.

All in all, he was a man.

So, it was with cautious optimism that I donned my favourite dress, put on some cute block-heel sandals (because, unlike the fuckboys at da club I was used to interacting with, men aren’t threatened by tall women), and headed out in the mid-spring sunshine to meet John at a local bar. I texted him as I approached the agreed-upon meeting spot.

I saw him exit the establishment. In the bright light of day, his grey-speckled, thinning hairline was obvious. He greeted me by sort-of-but-not-really kissing me on the cheek.

Oh no, I thought. He must be at least 37. No white man born after 1980 greets other humans with awkward cheek-kisses. I tamped down the bubbling feeling of mild panic, and John ushered me inside.

After acquiring our drinks (he was impressed by the “maturity” of my gin and soda), we settled outside to chat. The conversation was largely benign, though I do recall him referring to my status as a millennial on more than one occasion. I refrained from asking his age out of fear of his answer.

We eventually relocated to the second stop of the night: his friend’s art showing in the Distillery District, another activity that felt rather Adult™.

However, that illusion was shattered when he began drinking tequila mixed with white wine because the event’s alcohol selection was limited. Not to mention, the “friend” whose show it was was definitely a good 10+ years younger than him, as were all the attendees. I did a couple tequila shots for good measure.

Needless to say, we hopped in the Uber after the event quite a bit less sober than when we’d arrived.

In our tipsy state, we began recounting some of our previous dating ventures; I told him about Mr. Longboard and my handful of other less-than-stellar dating experiences. He decided to share the following story:

“Once, I went out with a woman, and she came home with me at the end of the night.” He had an impish grin on his face, his knee grazing mine in the backseat of the car. “As soon as we got in the door, she started kissing me pretty forcefully, and she started asking me to choke her and spank her. Isn’t that nuts?”

“Haha, yeah,” I said, a little unsure of how to respond to such a story from a strange man I’d spent less than two collective hours with. “I mean, to each their own, but that’s definitely a little aggressive for a first date.”

“It was kinda hot, I’m not gonna lie,” he said cheekily. “But it was definitely interesting.”

Interesting, indeed.

The Uber dropped us near where we’d begun our night; it was around 9:30pm, and since neither of our stops had included much food beyond hors-d’oeuvres, we both agreed a late night bite was in order. He led us into a rustic-chic Asian-fusion bar that looked like the sort of place I wouldn’t ever suggest unless someone with significantly more money than me offered to treat me to dinner.

We settled into our table and selected a couple plates for sharing, accompanied by a pair of exotic-sounding cocktails.

The ensuing conversation was innocuous enough that, combined with my alcohol-addled brain, I don’t really remember most of it. But, eventually, the subject I’d been furtively avoiding reared its head.

“How old are you, anyway?” he asked, raising an eyebrow.

“24,” I replied.

“Oh, really!”

“Why, how old did you think I was?” I inquired.

“I definitely thought you were more like 27, 28,” he said.

I was quite sure that was a lie, considering both my blog and my Instagram profile pretty clearly listed my age as 24, but whatever. It was time for me to find out the answer to the question I’d been fearing all night.

“Um, how old are you?” I said nervously, my voice unnaturally high.

“Well, I’m actually 40.”

My heart dropped. It was even worse than I feared.

“I understand if that makes you uncomfortable,” he said, having clearly seen through my attempts to swallow my horror.

In fact, it made me very, very uncomfortable. I launched into my spiel about my deep distrust of older men, especially those who explicitly seek out significantly younger women, and how I’m uninterested in dating anyone outside my personal age range, that is, five years older and one year younger (give or take of course, but 16 years was definitely way outside that allowance). How age rarely equals maturity, and about what I jokingly refer to as my “reverse daddy issues” (instead of an absentee father causing me to seek out authoritative father-like male partners, my extremely un-absentee father has resulted in an aversion to domineering men). How older men often seek out younger women because they think they can control them better, and dangle the coveted title of Mature For Your Age over their heads, ready to snatch it away at a moment’s notice if their younger partners dare to display any sign of a backbone.

Really, I could go on forever about my extreme and long-standing distaste for older men. But I tried my best to paraphrase, all the while keeping a faux-coy smile on my face meant to covey, “Don’t worry, I don’t think you’re creepy” (even though I definitely did).

“I totally understand where you’re coming from,” said John, when I’d finished my speech. “Personally, I just find myself attracted to youthful energy. My last girlfriend was 27.”

(Side note: I would like to take a minute to define the difference between men seeking relationships with significantly younger women and ending up in one. I am not inherently against relationships with age gaps, so long as both people are consenting adults. It is perfectly fathomable that two age-disparate people could organically meet, eg. through work, the gym, a class, etc., develop a bond, and naturally progress to a romantic relationship. This is very different from a man purposely looking for a younger partner.)

“Oh, yeah, that’s cool,” I replied, even though it wasn’t cool at all, as this put him firmly in that odious category of Older Men Who Actively Seek To Date Younger Women. “I think I’m also a little more wary of men fetishizing youth because I’m already fetishized a lot for being Asian.”

“Really?” he said. “I had no idea you were Asian.”

“Yeah,” I said. “Just half, though. My dad’s Korean.”

“Well, you don’t really look Asian to me, so I guess it can’t be that bad!”

Internally rolling my eyes at the caucasity (Caucasian + audacity) of this statement, I thought of the countless men who’d asked me, “What are you?” within minutes of first meeting me as if I was some kind of species of exotic bird, not to mention the “yellow fever” and “I’ve never been with an Asian girl” comments that I was all too familiar with.

“I think it’s really important to be open to new experiences,” he said, voice low, reaching across the table to stroke my arm.

I surreptitiously moved my hands to my drink, away from his touch. I was decidedly tipsy; enough that I wasn’t thinking as straight as I would have been ordinarily, but not so much that I wouldn’t be able to stick to my convictions if it came to it. “I will admit,” I said wryly, “it felt good to know I was going on a date with a ‘man’. I’ve definitely only really been out with ‘boys’.”

Which was true. In addition to Mr. I’m-27-And-Use-A-Longboard-As-My-Primary-Form-Of-Transportation, I’d also been out with a dude whose ideal first date location was apparently Subway, and another who’d inexplicably bought grapes and Coke in glass bottles to have as a snack while we drove around town and loitered at random parks (nothing against grapes or Coke in glass bottles, but just…why?).

In any case, it felt undeniably grown-up to put on a pretty dress and heels and meet a man at a bar, go to an art gallery opening, and finish the night in a swanky ill-lit Asian-fusion lounge where none of the cocktails contained Sourpuss liqueur.

Any fuzzy feelings I was having about the evening promptly evaporated when he opened his mouth again.

“That dress looks really sexy on you,” he purred. “You definitely have the body to carry it off.”

I immediately felt my fallopian tubes squeeze themselves shut to prevent any eggs from escaping my ovaries, lest I somehow accidentally fornicate and subsequently conceive any offspring with this man. I truly believe that the word “sexy” is, ironically, one of the least sexy words in the English language.

Ever the wordsmith, I replied with something along the lines of “Haha, um, thanks.”

“Anyway, I hope you’ve had a good time tonight, and that I haven’t proven any of your anxieties.”

“I did have a nice time,” I said, which was partly true. I’d been on worse dates, though I’d hazard to say that my enjoyment of the evening was more based on what it was conceptually rather than John himself. I’d gotten drunk for free, seen some art, eaten some tasty food, and hadn’t been seriously molested, which is always a win. On the surface, there wasn’t much to complain about.

I was, however, already planning how to dodge a goodnight kiss if such an obstacle were to present itself.

“I’ll leave it up to you if you’d ever like to do this again sometime,” he said.

“Yeah, definitely,” I responded noncommittally. I obviously had no intention of ever contacting him, but I feel like “Fuck no am I ever going out with you again you weirdo old man creep!!!!!” would have been a little overkill. “I should be getting home though, I do have to work in the morning!”

“Of course,” he said. “Gotta get your beauty sleep!”

He settled the tab (neither my pride nor my bank account extended enough to warrant paying any part of the $100 bill, and hey, he was a Man™ with a Career™) and escorted me down the street. He offered to get me a cab, but I insisted that I was fine to take the streetcar. He waited with me until the streetcar arrived, and when it did, I turned to him and said, “Thanks again for a lovely evening!”

“You’re more than welcome,” he said in that low syrupy voice. He reached for a hug, which I accepted. Before I knew it, his face was in front of mine and he was going in for a kiss; I kissed him back with even less passion than if he were a relative, lips pursed, eyes open, body stiff. Thankfully, it was little more than a peck. “Let me know when you’ve gotten home safely.”

And with that, I scurried onto the streetcar.

When I arrived home, tipsy me felt it polite to make good on his request. I texted him that I had indeed gotten home without incident and thanked him for the evening, again reiterating that I’d had a nice time.

I had a lot of fun tonight too, came his reply. I would like to see you again soon, unabashedly. And you looked really hot tonight [insert blush here].

Y’know we millennials have these hot new things called emoji, I goaded playfully, adding said emoji for emphasis.

Tough crowd is allz I’ll say, he said, accompanied by a group of emoji of his own.

When I awoke the next morning, the sparkle of alcohol having been replaced by the vague fogginess of a mild hangover, I read the last texts I’d exchanged with John and felt a squirm of ickiness, both at him and myself. “You looked really hot tonight [insert blush here]”??? And I replied with flirtatious teasing and cheeky emoji??????? Sober me would have replied with, “Haha, thanks” at most.

I thought about the mounting sense of unease that pervaded the previous night, and the strange act I’d put on. The cool girl, benevolent and consistently unruffled by the unexpected, coy and flirtatious, metaphorically fluttering a Victorian fan across my face. Why had I behaved like this? Why had I felt the need to keep up this facade and see the night through, despite the fact that, if I’m being honest, I began feeling partway through the night that I’d much rather be at home watching RuPaul’s Drag Race and passing around a family-sized bag of No Name-brand dill pickle chips with my roommates?

I waited so long to write about this for a couple reasons; first and foremost, because he jokingly mentioned at one point that he hoped he didn’t become a blog post (whoopsies). But now that I’m no longer at risk of running into him on the street, and now that my Canadian number is out of service, I’ve taken the liberty of blocking him on Instagram, so unless he decides to seek out my blog of his own accord, I should hopefully be safe from any awkward confrontations.

Secondly, I can’t help but look back at the whole experience without feeling that my feelings of revulsion seem like a vast overreaction when I consider the actual events of the night. Really, what had John done, besides be old, tell an inappropriate story about a prior date, and give me a really awkward compliment? I’ve had far worse experiences with men and will likely have more, but this interaction has stood out to me in the year since it transpired.

I had some difficulty sorting out my feelings about my night with John until a certain short story was published in the December 2017 issue of the New Yorker. For the uninitiated, the story to which I am referring is “Cat Person” by Kristen Roupenian (which you can read here). A quick summary for those who don’t feel like reading it: College sophomore Margot develops a textual relationship with 34-year-old Robert which eventually culminates in them spending an evening together. Margot is a bit of a narcissist, and Robert is a bit of a weirdo who ultimately turns out to be a huge dick. While the story itself isn’t without problematic aspects and the prose, in my humble and unseasoned opinion, is merely serviceable, “Cat Person” struck a chord with millions of women across the Web upon its release, leading to a wide discussion about enthusiastic consent, the male ego, and women’s socialized responsibility to cater to that ego, all in the context of our post-Weinstein world.

There were two specific points about “Cat Person” that struck me personally. Firstly, had the story been told from Robert’s or even an objective third party’s point of view, we likely would never have known that Margot isn’t all that jazzed about the encounter. While the reader knows that every step she takes is preceded by a considerable amount of self-steeling and self-convincing, to anyone outside of her brain, she would seem to be an active, willing participant. She insists that they go for a drink; she suggests that they leave the bar and takes his hand, leading him out, then proposes his house as the destination; she actively straddles him twice during their encounter; she takes her own shirt off and unhooks her own bra. Yes, she was tipsy, but that was also of her own volition (and in the context of “battling her will into submission”). Robert didn’t deceive or pressure her into drinking more.

Similarly, there’s almost no way an outside observer would have ever suspected that I wasn’t 100% A-OK with everything that was going down. I laughed, I flirted, I agreed to second and third rounds. I too readily played the part of willing participant.

I think the problem is nicely summed up by the following passage:

“[T]he thought of what it would take to stop what she had set in motion was overwhelming; it would require an amount of tact and gentleness that she felt was impossible to summon. It wasn’t that she was scared he would try to force her to do something against her will but that insisting that they stop now, after everything she’d done to push this forward, would make her seem spoiled and capricious, as if she’d ordered something at a restaurant and then, once the food arrived, had changed her mind and sent it back.”

Time and again, we’re shown examples of women trivializing their own feelings for the sake of not seeming “difficult” or “stuck up” or “bitchy” or other similarly unflattering adjectives. True to my procrastinatory nature, I put off asking John how old he was until the end of the evening; though I was pretty sure from the beginning that he was much older than I was comfortable with, the lack of confirmation made it easier to see the evening through. If I had been truly comfortable and confident in the situation, I would have asked how old he was immediately after his weird old-person-cheek-kiss, said, “Sorry, but you’re too old for me. Sayonara, Gramps,” and bounced right outta there. Of course, like Margot, I didn’t feel necessarily threatened by John, but the fact remains that I ignored my gut feelings and pushed forward purely for the sake of saving face. There was not a single piece of me in any point of the night that considered I might be interested in pursuing a second date, even if he hadn’t done anything off-putting. I was riding the wave to completion almost entirely out of politeness. Point being, we shouldn’t have to “battle [our] will[s] into submission.” We should feel comfortable expressing our feelings outright.

The second point concerns my aforementioned distrust of older men. There’s a distinct parallel to be observed between John and Robert, exemplified in the following exchange, which happens near the end of the story immediately following Margot and Robert sleeping together:

“‘How old are you, exactly?’ she asked him.

‘I’m thirty-four,’ he said. ‘Is that a problem?’

She could sense him in the dark beside her vibrating with fear.

‘No,’ she said. ‘It’s fine.’

‘Good,’ he said. ‘It was something I wanted to bring up with you, but I didn’t know how you’d take it.'”

It’s no coincidence that both John and Robert waited until the end of the respective dates to discuss age. And of course “Cat Person” is a work of fiction and Margot and Robert aren’t real people, but writers are required by trade to be deliberate with their words and short story writers perhaps even more so. Including this scenario wasn’t accidental.

The thing is, most older men know, at least subconsciously, that significantly younger women probably don’t want to date them. I don’t think it was a fluke that John waited to bring up the subject of age until the end of the date, and following his age with the disclaimer that he would “understand if it made me uncomfortable” implies that he knew it was a real possibility. Even if he hadn’t been lying when he said that he thought I was 27, 13 years is still a significant enough gap that most wouldn’t take it lightly. That’s an entire teenager.

While I won’t deny that the reverse exists (to a much lesser degree), older men’s attraction to younger women is an undeniable pattern. In fact, men will even lie about their ages on dating sites in hopes of snagging a younger catch. It’s sad, really; men shave years off to hit on younger women, and women shave years off simply to be seen as desirable for age-appropriate men because said men are too busy chasing college girls.

It’s true that sometimes the reason men desire younger women is pure sexism (you know, because men age like fine wine while women become increasingly shrivelled hags). However, sometimes the motives are much more sinister. Sometimes, older men want a younger, less experienced partner because she might be more likely to put up with their bullshit because she hasn’t yet learned better. Or perhaps they relish the prospect of manipulating and grooming their younger partner into being exactly the woman they want her to be. Or maybe they get off on the prospect of being automatically regarded as wiser due to age, as being thought of as a protective and father-like figure, rather than as an equal partner in a balanced relationship. In the end, large age gaps only serve to widen the inherent imbalance of social power between men and women.

To John’s credit, he made good on his promise to leave the ball in my court and never tried to contact me again. Unfortunately, he eventually got a job a mere two blocks away from where I worked, meaning that we occasionally frequented the same areas. I’ve encountered him three times since that fateful night.

Once, I passed him on the street, my breath held; thankfully, he didn’t seem to notice me.

The second time, I spotted him outside his building as I was making my way to work, causing me to immediately shove my face into my phone with much greater fervency than any normal person would. Unfortunately, he didn’t seem to get the message, because he got my attention and insisted on walking with me. I managed to casually mention the existence of my girlfriend at the time, though because he’s old, I can’t be certain if he understood that I meant “girlfriend” in the romantic sense or if he just thought I was referring to a friend who was a girl, as people my mother’s age are wont to do. Upon my escape, I immediately collapsed into the arms of my coworkers, laughing shakily.

The final time was his first reappearance at the restaurant since our date. I cursed my misfortune of being on shift at the time of his visit, nervously rang through his fries while maintaining my weird high fake-cool voice, and giggled nervously with my friends the second the door closed behind him (I had, of course, debriefed the original encounter with them).

I sincerely hope I never encounter him again. My awkward, nervous heart can’t take it, and I can’t help but feel mildly offended by my own behaviour and the oddly chill demeanour I seem to adopt whenever I see him, so contrary to the millions of tiny snakes that seem to take up residence in my internal organs.

To be fair, if John were to ever come across this account and subsequent analysis of our evening together, I truly think he’d be remorseful for causing me such discomfort. I don’t think he was acting out of malicious intent. I think such scenarios are merely more evidence of the various ingrained notions those socialized as men tend to exhibit. As I have spoken about before, if we truly want to mend the many wounds in our fucked up world, self-reflection and self-improvement is a necessity.

I suppose my ultimate question to older dudes who purposely seek out younger women is this: What could I, someone whose 2018 New Year’s resolution was to obtain as many velour tracksuits as possible, possibly have to offer a person who has not only started his career but is solidly in the midst of it? I mean, besides the obvious? If it’s a matter of being “young at heart” or whatever, why not find an appropriately-aged woman who is also “young at heart”? Truly, when you think about it, there is absolutely no good non-gross, non-sexist/ageist reason.

In conclusion, I’m really not trying to claim that I was left deeply traumatized by this incident. I suppose it’s not much different from any awkward dating situation that ended less-than-pleasantly. I just chalk it up to a learning experience, and hey, I (eventually) got a blog post out of it.

I will say, though, that my love for my favourite dress has been marred slightly, for every time I put it on, I think about a man who seemed more likely to be friends with my parents than my date calling me “sexy”. So please, gentlemen, if you take anything away from my endeavour, I urge you to never, ever tell a woman (especially one you just met) that she’s sexy. There are a million other adjectives with which to compliment someone, and all of them are patently less vomitrocious than “sexy”.


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