There’s good-weird and there’s bad-weird, and there’s so much in between, and the highly subjective differences are part of what makes dating culture so fascinating.

In the Toronto Star’s popular relationships column “Dating Diaries,” many of our diarists describe situations in which the already awkward nature of a date is exacerbated by the relative “weirdness” — which is usually well-intentioned, or at least authentic — of their date.

(If you have a story to tell, we want to hear it — details on how you, too, can become a dating diarist at the bottom of the piece.)

“Alyssa” met tall, fit, well-dressed, funny “John” at the gym and was “really happy” when he asked for her number. He invited her to a dance, which Alyssa didn’t think she’d like, but she was excited to go out with him and agreed. Then, she wrote, “A few days before the date, John called me again. He told me not to get too dressed up for the dance — because for part of the evening, I would be helping him serve the guests. I was speechless. I think I eventually responded to this detail with ‘What?!’” The event was being held at a club John belonged to, where members help out at events. Unlike many diarists, Alyssa actively agreed to the situation she found so odd. She wrote that “Even after I decided to give him the benefit of the doubt, I was still flabbergasted.”

Alyssa ended up having a great time — with the other people at the club. “At the end of the night, I told John I was getting a cab. He said that he was going to help clean up for another hour and that if I waited, he could drive me home. Seriously?!”

“Nate” and “Abigail” were having a great time on their date when a fake “rescue” call came from a friend. Abigail said that Nate was “wonderful,” but it went south when Abigail “casually stated that she didn’t believe in some very common medical practices.” Nate wrote that “Abigail’s eyes were almost glazed over, as if she was confident she’d found a fellow traveller, and I voiced no objections. I find there isn’t much use in saying anything when someone is on a roll like this.” He told her he was going to the washroom and, instead, he “approached the hostess, paid the bill for both of us and asked her to tell Abigail I wouldn’t be coming back.” Nate wrote that he “felt the same way that I’m sure many women feel after dating men they meet online: ‘Are there any sane people out there?’”

When “Andy” met “Pamela,” he was dating “very frequently and maybe a bit indiscriminately.” He was looking for someone “with humour, class, education and that je ne sais quoi of I have no idea. Pamela was introduced to me by a mutual friend. She was pretty and a bit nutty, which is almost a prerequisite for me.” Good-nutty, that is. After a successful date at a coffee shop, Andy made a reservation at a nice restaurant, with high expectations.

“Some five minutes into the soup, however, Pamela blindsided me, and interrupted the so-far so-good conversation, by announcing that she had a big secret: she was born with psychic powers. Understandably, I thought at first that she was joking and it took a bit of serious insistence before I figured out that she had meant what she said. I’m a scientist; it was hard for me to go along with this.” When Pamela pulled out a deck of tarot cards, Andy played along. “Humouring her, I pulled out a card, which was the card of the hangman. She told me it was a ‘great start’ and that it meant that I was facing some kind of suffering. I asked her if she was talking about right now, making a joke. She didn’t seem to get it.”

Similarly, “Lulu” was drawn to “Michael” because he was quirky, “maybe even odd.” She wrote that “it made it easier to think about meeting him in person,” because he seemed more real or familiar. They planned to meet for coffee and, on the way, Lulu was “nervous, excited and scared.” Earlier, Michael had texted, “You won’t miss me.” Indeed: he “showed up in an almost full set of actual armour.” Lulu wrote that the other patrons “fell silent as he slowly made his way toward me. Every single person at the cafe was staring at us.” The suit made it difficult to sit down, but Lulu wrote that Michael was “clearly enjoying the attention.” To top it off, “the conversation was completely one-sided, which didn’t help him any.”

The love lesson? Be up front with who you are on your dating profile so the right people respond and, when you’re out, prioritize your date’s comfort and leave the stranger stuff for another time. You never know: maybe they’re even weirder than you.

Want to be a dating diarist? Email datingdiariescontact@gmail.com



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