Ever wondered what it would be like to date your favourite Canadian city? Of course you haven’t because that would be incredibly weird. But say the characteristics of your favourite city were manifested in a beautiful woman? Still, that’s probably pretty weird. But lets do it anyway. This is my interpretation of what it would be like to date each Canadian city…if they were in fact woman.
Let’s work our way West — East.
You took one look at Vancouver and were like “Yup!” By the way of first impressions she was the dream. The minute you laid eyes on her you felt like you were some line in a corny love song. Her face glowed, her long summer dress swayed as she moved with the music. Vancouver was a stunner who seemingly had everything — the expensive clothes, the perfectly sculpted yoga body, and her amazing and luxurious family-owned summer and winter cabins you could jet off to on the weekends. But behind closed doors, Vancouver’s dark side was quickly revealed. She was pretentious, cliquey, had a hard time accepting your quirky friends, and when she was hungry she became so verbally abusive to the point you could only meet up with her right after she had eaten. Her group of friends were also cold, status-obsessed, and gossipy, to the extent you started catching yourself mocking them by saying “xoxo Gossip Girl” at the end of every single one of their sentences. Vancouver also loved to live the life of riley, which forced you to live well above your means all so you could keep up appearances and live the good life. Also, your sex life was a complete disaster. Sure just looking at her made your dick hard, but it wasn’t enough. She was boring and uninteresting in the bedroom — she only liked to do it in the missionary position and would get crabby if you took too long to cum. Also, she didn’t give blowjobs…like ever. Eventually you started faking your orgasm, then going into the bathroom and turning the fan on and pretending to take a shit just so you could finish yourself off. Finally you couldn’t deal with this basic bitch any longer and so, you started looking for girls with actual personalities. Vancouver wasn’t fazed. Within a couple days of the breakup, she was already batting away legions of men with her Stilettos. You soon found out she started dating the captain of your city’s NHL team right after you. While you only dated for a couple of months and you know the breakup was for the best, you still catch yourself staring at her photo online and bragging to your friends about how the captain of your hockey team is banging your sloppy seconds.
Vancouver is the hottest girl you ever dated.
You met Calgary when she was near blackout at the bar. She took a double shot of Jack, then proceeded to steal your hat and make fun of your shirt. You took her home that night and she rocked your world. She road you rough and made you question your manhood. Your relationship with Calgary was an unusual one, as she was tough in a way that you weren’t used to with prior women. She loved to ride motorbikes, race horses, and snowmobile through the backcountry in the winter. While these activities didn’t interest you, you idolized her for them. But your differences continued — her rural upbringing made her a little bit racist and unaccepting of those who were different than her. You’ll never forget how she went ghost white when she saw her first black person, or how she would violently curse out her window every time she saw a Chinese person drive straight with their blinker on, or make a very indecisive, meandering left. But these racial outbursts were completely abolished for the fact that Calgary let you invite other women into the bedroom with you. Not only that, but going out and selecting women to bring home for the night became one of your favourite activities to do together. This new sexual chapter with Calgary was amazing, up until you guys met Edma one night. Edma also loved to ride motorbikes, go horseback riding, and snowmobile through the backcountry. Soon it became nothing more than you sitting on the sidelines, watching Edma bang your girlfriend with a strap on. Eventually it got to the point that her and Calgary were spending weekends in the Rockies with their horses. This all coincided with her behaviour toward you becoming completely bi-polar. She was hot and cold — she would be present one minute, then the next she would be texting and giggling with Edma, acting as if you weren’t even there. You had no idea what to expect from her, and slowly, her lack of consistency drove you crazy. Finally Calgary came out with it and told you that her and Edma were in love and they were moving out to a farm in the country to raise cattle together.
Calgary is the girl that left you for another girl and used the Brokeback Mountain plotline as a punch line.
You met Saskatoon when you were 15. She was your high school sweetheart. You went to college together and ended up living together through most of it. You had your whole life planned out together. You were “that couple” that everybody figured would be pregnant at your college graduation. BUT! On the eve of your college graduation you had an epiphany and realized you didn’t want the life you’d be working towards with Saskatoon. You still had so many things to do and right now you were en route to an early death. She wanted you to take that job offer that was handed to you right out of business school, move in together, and start creating an “adult life” together. She basically gave you an ultimatum that you put a ring on it or she’s out. But you felt like an animal that had been held in captivity for most of his life and needed to break free. So what did you do? You dumped Saskatoon the day after graduation and fucked your way around the world. You made up for the lost years Saskatoon had dragged you down for (3 years of high school + 4 years of college= 7 lost years of random and meaningless sex), and indulged yourself in cheap rub-and-tugs, hookers in Amsterdam, and endless Scandinavian women down under in Australia. You were finally living it up and had cast aside that anchor that’d been holding you back for years. You were only with Saskatoon because you didn’t know any better. She was that relationship that you fell into before you even know what relationships are, like a kidnapper who captures and brainwashes its victims when they’re young, impressionable, and unable to comprehend reality. Finally, you were rescued. Years later you find out that Saskatoon is already divorced. Apparently she married the next guy after you, gained a bunch of weight, moved into a town with a population less than your graduating class, and had to file a restraining order against her alcoholic husband for domestic abuse.
Saskatoon is the bullet you dodged.
You met Winnipeg on a cold, dark November night. You saw her from across the room and didn’t feel a damn thing, but she came up and started talking to you. At first, you didn’t want anything to do with her, as she was annoyingly plain looking and with style that looked like she was on the set of Little House on the Prairie. But the dark season (winter) was coming and you didn’t have any prospects in the pipeline. So you decided to give her a chance to warm her way into your heart and see if you could grow to like her. She also had a beautiful, cozy basement suite apartment, right near the subway, which made it convenient. Together you both swore off all your friends and let your lives fall apart all so you could be lazy in a relationship that would inevitably melt in the spring. You spent your days cooking in sweatpants, watching entire seasons of shows without showering, and indulged yourself in every delicious treat you could get your chubby hands on. The best part was that Winnipeg was head over heels in love with you – she would give you the best foot rubs, massages, run you baths, and serve you tea in any naughty outfit of your choosing. Winnipeg was the perfect temporary companion. She also gave you a Valentine’s date for the first time in years and made you feel like a sex hero by the way of how loud she moaned and how much she came every time you had sex, as if she was being paid off to stroke your ego. Only problem is that you knew deep down this relationship wasn’t going to last. You were only with her because her appearance matched your circumstances — winter was approaching, she was there, and you didn’t want to hibernate alone. Eventually the spring sprung, the legs came out, and you realized that you’d been living in an igloo with a girl way below your pay grade.
Winnipeg is the hibernation partner you settled for.
You met Toronto at an after hours club. She had a glow stick in her mouth and was wearing a plastic headband. You were in a very “experimental” phase after just recently getting out of a complicated relationship (and would rather people just not ask questions why you were at an after hours club in the first place). At first look, Toronto seemed like nothing more than the type of girl you would buy MDMA off in a sketchy underground bar. She was modestly attractive on a good day, with a little extra meat padding around her sides. But you were kind of in a dark place at the time, so you decided to throw caution (and standards) to the wayside and tried Toronto out. But…boy were you mistaken. Toronto was interesting, energetic, fun to be around, and up for absolutely anything. Sure she may not have been the most attractive girl you’d been with, but she surely put up a fight to be the coolest. The sex was also the most uninhibited and outlandish you’d ever experienced — Toronto was an absolute beast in the sack. She didn’t lie there and just take it. However hard you banged — she banged back twice as hard. Whenever you were about to cum, Toronto would roll over and let you cum on her back. What a ride this relationship was. The only problem is that Toronto was slowly turning your life into a destructive film noir movie. You were experiencing massive mood swings filled with euphoria and rage, sleeping in all afternoon, and trying to live your life as a functioning alcoholic. You finally realized you had to make a change when you woke up in the middle of the night on a Tuesday to the sound of Toronto bumping a line off your bathroom counter. You broke up with her the next day and immediately drove yourself to the doctor’s to get tested. As expected, Toronto gave you Chlamydia. You’ll never forget Toronto. You had never felt more alive than when you were with her (or on you way to an early death). Your relationship with Toronto was completely exhausting and took a good 5 years off your life and led to you taking a hiatus from women all together.
Toronto is the pill-popping party chick that gave you your first STD.
Ottawa was the daughter of a friend of your mom’s. You guys were set-up because you were both single, therefore your parents figured you would perfect for each other (god dam shitty parent dating theory). You were reluctant to go on the date because you knew she would suck. As you predicted, Ottawa was a complete bore. She worked in…uhhhh you can’t even remember what she does because it was that unworthy of remembering. She works for the government or something? No middle management for some food ingredient company. Yes that was it. It even sounds depressing to say, let alone devote your life to. But you had absolutely nothing else going on at the time, were running through a turbulent period of low self-esteem and lack of self worth. So you went along with it and decided to date outside of your type and try something new. You went with her to her wine and cheese parties, her book club group mixers, her animal cruelty rallies, and put up with her crazed feminist outbursts (Yes you guessed it, Ottawa is a feminist). Sure it wasn’t the most exciting time of your life but you were in a practical, and stable relationship that helped keep you out of trouble. Ottawa also smelled fantastic and had the nicest vagina you’d ever seen. If your dream girl was solely based around personal hygiene, then Ottawa was the girl of your dreams. Also she dressed well, took care of herself, went to the gym, and never did anything disgusting, which made her seem all the more pleasant. So you continued to mold and restrain yourself to accommodate Ottawa’s dull persona. You watched the news for once, got into politics, read novels, and started actually paying attention to world issues. For a while there, you were the perfect boyfriend. But of course it didn’t last. One night Ottawa ran into you at the bar when you were blackout drunk with your friends and pissing in the corner of the bar. She tapped you on the shoulder and told you that she couldn’t be with you anymore because she couldn’t risk hurting her future political career. Off she went, right into the arms of some vegan accountant with a unibrow who canned his own produce and wrote a feminist blog.
Ottawa is the girl you look back on and can’t believe you dated.
You met Montreal out front of an ESL school. She was living in your city (country) for a year to learn English. Her dark olive skink, chic bohemian style, and broken English had you smitten within days. The romance was explosive. Filled with passion and adventure, a lot of sex, and very little talking. She was your first foreign girl, which opened you up to whole new relationship dynamic. She would cook you delicious meals while you watched your favourite shows and then give you a blowjob for dessert right there in your living room. God dammit it was fantastic. Montreal was so giving. It was a time of love and learning. Montreal taught you how to properly give a girl cunnilingus, drillling you until you brought her to orgasm every single time within minutes. You felt like you were living in a Woody Allen movie — biking and taking picnics in the park, romantic weekends away, spontaneously fucking in every random location possible, attending numerous art shows, even taking a sculpting class together. Montreal awoke your inner artist and really showed you how to experience true passion and express yourself in ways you’ve never explored. But as the relationship progressed, Montreal began showing some real red flags. She was jealous, possessive, intense, and demanded too much of your time. She would literally snap at you in her native tongue anytime you came close to looking at another girl when you were out, would incessantly text you when you were out wondering what time you were going home, even stealing your phone and checking your messages while you were asleep. You lost all contact with your friends, particularly your female friends and had to become completely devoted to Montreal, and nothing else. One afternoon you lied to Montreal and told her you were going to run some errands when you were really going to catch up with an old girl friend of yours that was just in town for the afternoon. You’re pretty sure she followed you that afternoon because when you got back home everything was gone. Montreal had stolen absolutely every possession of yours, a complete Grinch cleaning. She even took your passport and all of your clothes. All that was lying there was your bare mattress on the floor, with a sticky note on the wall above that read “You’re never going to see or touch my vagina again” Weeks later you see Montreal on the news — she was arrested for fraud and money laundering and setting up fake bank accounts with the Swiss bank — some real Girl With The Dragon Tattoo type con-artist shit.
Montreal is the foreign girl who gave you a summer of sex-education and then stole all your shit.
You met Halifax at a backyard summer barbeque. She was drinking a tall can of Wildcat, wearing plaid, and loading up a hot dog full of around 8 different condiments. You knew immediately that this wasn’t your average chic. That’s because minutes after meeting you she paused, and continued to belch something that sounded like it should have come from some 300 lb. football player. Also, you spent the first half of your relationship thinking she was Irish and trying to understand what the fuck was coming out of her mouth. This problem doubled in significance when she was drunk, and she was drunk A LOT. So a good portion of your relationship was spoken in gibberish. So what? You had a hard time understanding her and she had a tendency to do some very unladylike things, no big deal right? Halifax remained to be one of the most genuine, kind, and wholesome girls you’d ever met. Her family was awesome and welcomed you in to their clan as one of their own. You felt loved, wanted, in a way that you hadn’t even felt with your own family. So you decided to put up with her real “dudey” behaviour, the way she would chug a beer can and proceed to smash it on top of her head, as well as the fact that it seemed like every day was laundry day because she didn’t even own one single pair of sexy underwear. No thongs, G-strings, nothing, just straight up parachute underpants. So you could put up with all this, right? Well, to most guys this girl was a dream girl — she loved football and was athletic, wasn’t high-maintenance or pretentious in the slightest, didn’t need to go out to fancy places and was actually at her happiest having a pint at the local pub with good friends. It was a nice change for you to not have to worry about impressing a girl, and instead you could just relax and be completely yourself. But eventually you couldn’t handle that she always seemed to hang out with guys who were close like brothers, the fact that she could outdrink you on an empty stomach, and the way she would wear Sketchers to important dinners. You broke up with Halifax because you were tired of being in relationship that made you feel like a woman.
Halifax is the tomboy that you couldn’t bring yourself to love.