Dating Diaries: ‘I started getting annoyed that he wasn’t asking me any questions about me — but he did compliment my looks a lot’

For more than 10 years, first-person accounts of the best, worst, weirdest and most interesting dates in Toronto have made the “Dating Diaries” column one of the Toronto Star’s most popular reads and a flip-to-it-first destination in the Saturday paper. (Before the Star, the column ran in Eye Weekly and The Grid, both Star-affiliated weeklies.) Which means, there are a lot of lessons to be gleaned from other people’s bad dates. (We want to hear your dating stories, too — details on how you, too, can become a dating diarist at the bottom of the piece.)

Not all of the dates featured in the Dating Diaries are first dates and not all of them start online, but they all include two people making an effort, with many different results, to connect with each other. With so many Diaries come more than a few lessons about dating and relationships and, with dating in real life on the up again, we thought we’d take a look at some of them.

By far, the No. 1 thing that most daters get wrong on their dates (which is then usually reflected in a low “out of 10” score) is not asking questions. Honestly? Even one question is a good start: over and over, our Diarists report that their date didn’t ask them “a single question.”

Diarist “Georgia” wrote that her date, “Davis,” only talked about himself: “I started getting annoyed at the fact that he wasn’t asking me any questions about me. In fact, he didn’t ask me a single question about myself — not even the basics like where I grew up or went to school — but he did compliment my looks a lot. It should have been the other way around.”

In a Diary about a pair that met at a speed-dating event, “Elizabeth” wrote: “After two hours and not being asked a single question, I said ‘Maybe we should just get the bill’” and her date, “William,” told her what she owed and to “pay up.” It’s probably not a coincidence that “William” failed to hit the mark on two different kinds of generosity. (Offer to split the bill, sure, but “pay up”?!)

It should be simple. If you’re not going to ask questions to demonstrate curiosity or even basic interest, what’s the point of going on the date? The daters who don’t ask questions are usually happy to talk about themselves. “Marnie” wrote that “the wait to be seated and served at the busy sushi restaurant — where we didn’t have a reservation, of course — was approximately 45 minutes. Bob proceeded to talk about his childhood, education, travels and personal interests. He enjoyed talking about himself … a lot. It became clear that he wasn’t going to ask a single question about me.”

Sometimes, a date might just not want to be there, or feel shy, awkward or out of place. “Kelly” wrote about asking her date “Darrell” some questions about his hobbies and says, “He was slouching around and not making eye contact. He didn’t ask me any questions or follow up on anything I was asking. In fact, it seemed like I was the one annoying him.”

Knowing how to volley in a conversation is one of many social skills that has become endangered as formal etiquette fades away and our social focus is absorbed by the internet, in particular social media, and for single people, the churn and gamification of online dating.

It has to be said: most of the no-question-askers who appear anonymously in the Dating Diaries are straight men. This could be because men are not socialized or encouraged to be vulnerable, especially in situations like a first date. It might feel uncomfortable to focus on getting to know their date instead of trying to communicate information about themselves. It might also be that women are often hesitant to state their own needs, so the no-question-askers may not even be aware that they’re creating a conversational void, even if it’s pretty obvious to their date.

The solution? Ask a question. A conversation, especially on a date, should be a rally, not a monologue or an interview. Start with the usual icebreakers, and pay attention to the details your date offers up and go further: How did you get into that industry? What’s the best concert you’ve ever been to? How did you come up with your dog’s name? Or try this one: Am I asking you enough questions?