10 Canadian Women Reveal First Date Stories That Will Make You Cringe

Who says Canadian women aren’t adventurous? Joanna learned the hard way that Canadian women dating abroad can suffer the same first-date mishaps as those dating back at home.

“We settled on a place literally next to my apartment — but he insisted on picking me up to walk me there. He arrived in an Audi convertible (which I actually learned was his dad's — not his), we spent 20 minutes driving in circles in Barcelona looking for parking, just so he could look cool. On the date, He proceeded to brag about how his boss has no idea that he plays video games and Facebook all day at work, and he gets away with doing nothing (he thinks this is funny for an ambitious woman like me). Fast forward 1 year, I walk into his office as a new manager…”

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Canadian Reddit user LieutenantCrispy tells us: “I went on a Tinder date with a guy who lived in my area. Since it was a first date and I wanted to make a good impression, I dressed up a little. When I met up with him, he was in flip flops and a zip-up hoodie. In late October. I felt like Beyoncé next to Ed Sheeran. Not a huge deal, but I did feel a little thrown off by his lack of effort.” From there, things only got worse. “When we got to a bar, it was completely up to me to keep the conversation rolling. When it came time to pay for our drinks, he literally did the snap snap thing to the waiter. The only reason he wanted to leave was because a live band was setting up and he said he didn’t like music.” Hold on – who doesn’t like music? “As we’re walking out, he asks if I want to come over as his parents aren’t home this weekend. I started wondering if I had accidentally gone out with a high schooler, but he was definitely 24 years old. He almost followed me home, continually asking if I was sure I didn’t want to come back with him.” Yikes.

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In a bid to get out of her comfort zone, Agnes looked to a dating app. “I was excited to meet this guy from a dating app. He was a tall, dark, handsome ex-cop-turned-lawyer. We agreed to have drinks at a local pub during the week in the late afternoon to keep our first meet casual. Flash-forward to us ordering drinks: I ordered a beer, he got a vodka and soda. I casually started a conversation about drink preferences and asked him his feelings on beer.” According to Agnes, this is when it took a (wrong) turn: “His response was, “Well obviously I like beer, but it just doesn’t seem like an appropriate drink choice for a date OR a girl for that matter”. I made a point of finishing my “inappropriate” beer and left. We never spoke again.”

Kingston resident and Quora contributer Racheal Blair tells a first-date story that has her her date shirtless — with Quizno’s on the itinerary. After demanding Racheal pay for her meal, her date took her to The Brick to kill time before their movie, where he spent the whole time landing on her cheek as she rejected his attempts to kiss her. Think it can’t get worst? Think again. Racheal recounts the end of the (horrible) night: “He drove me home, where we ended up in a minor car crash for my parents to see. No damage was done to his car that day, but I'm certain his ego was bruised.”

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Quora user and Toronto-resident Aarden Hartle wrote about her worst first-date experience, saying in her story summary: “My date showed up late, stoned out of his mind. He got drunk, and demanded I pay for the meal when I wouldn’t sleep with him.” While we’d love to tell you that the full-length story reads more favorably about her Tinder-date – we just can’t do that.

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Vancouver resident Louise was a 54-year-old divorcée looking to get back onto the dating scene. When matchmaking at the hands of her friends didn’t work out, she turned to online dating. Of her (many) cringe-worthy stories, we opted to share this one: “I will never forget the dear man who experienced a psychotic break. In my car. We called it a day and I drove him to his hotel. The next morning, I took him to breakfast. “This is beyond me,” I explained. “I hope you get the help you need.” He nodded, “I totally understand. Thank you for your kindness.” Within the hour, he was on the ferry sailing back to Vancouver.”

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When Hamilton native Mandi agreed to help out a friend by accompanying him to his legal firm’s welcome dinner, she had no idea that the “welcome dinner” would end up as an intimate dinner for two. But before you go thinking this was all a ruse to sweep Mandi off her feet, think again…

“He didn’t bother with the firm’s (welcome dinner) fare, and instead ordered off the menu, and he was quite liberal with the plates and the wine. From there on in it was one word answers. When the check came, he waived it over to the table.

He insisted on accompanying me home on the subway, and asked for his fare. At my door, he asked for fare home!”

Ottawa resident and Quora user Karen Opas recalls her time working as a waitress in a restaurant that often played host to “upscale business lunches” for CEO-types and the like. After two years of serving a businessman some 40 years her senior, Karen finally agreed to go on a date with him.

“We had a lavish dinner in the rooftop ballroom of the Hotel Vancouver. There was a big band orchestra playing and, despite the fact that I didn't know a thing about ballroom dancing, he got me out on the dance floor several times. I was having a great time and so was he,” says Karen. Do you feel a twist coming too? “During the last dance, I decided to try and do the swoop with him in my arms. Did I mention that he was 6' 4? Over a foot taller than me. I dipped him down and then I dropped him. And then I fell on top of him. I broke his collar bone. We spent the rest of the evening sobering up in the Emerg at VGH. He kept coming back to the restaurant, but he never did ask me out again.” Let’s not play the blame-game on this one, shall we?

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Toronto resident Mira learned the hard way that when a match sounds too good to be true — it usually is. “My friend had been badgering me about giving this guy she knew a chance. She said he was a perfect match for me. He sounded pretty great, so eventually I gave in. So we go out, and right away, I can tell that this guy’s personality is nothing like my friend described. It all went downhill when I asked him how he knew my friend. He shrugged and said, “Well, I kept asking her out and she kept saying no. I guess I wore her down because eventually she said she had someone in mind who would be perfect for me. I guess that’s you!” Needless to say, there was no second date, and my friendship fizzled out pretty quickly after that.”

Toronto resident Agnieska shares a first-date story that left her dealing with a gutsy request. “During a day-time date sipping on iced coffees, I told my date a fun story about a few friends and I from the previous night. He was intrigued and kept asking me follow up questions about my friends and stuff. I was excited that he was showing genuine interest. That is, until after a few minutes, when he told me, "Wow, that friend sounds exactly like the type of girl I'd be attracted to — can you set me up?" We’re betting the answer here was a hard no.

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