Home Health I asked him a lot of questions. But he didn’t ask anything...

I asked him a lot of questions. But he didn’t ask anything about me: Dating Diaries


Erica is a 33-year-old brand manager who lives in Bloor West Village. She says, “I love dresses, skirts, flared jeans and bohemian shirts. I would say that I am really good at dressing up an otherwise casual look.” She says she is “intelligent, positive, affectionate, easygoing, inquisitive and always ready for an adventure.” Erica likes to do yoga and dance and is hoping to foster a dog. “Before COVID, I usually suggested active dates, like drinks at an arcade or a ping-pong bar. I find this gives me a better idea of the personality of my date, like if they’re fun or competitive.”

Over the past several years, I’ve gone on a lot of dates, but few of the guys left a lasting impression. Not interesting, not good listeners, not empathetic, not great personalities. I’ve had success on dating apps, but men don’t always take it seriously. It takes two weeks for them to plan a date, or they show a general lack of interest in getting to know me. Those dates don’t often hit the mark.

I met Aidan on an app. I was interested in him because he was attractive and seemed really sweet. We exchanged numbers and continued our original app conversation over text. At one point, Aidan asked if I wanted to speak on the phone instead, because it was easier than texting long messages. I thought that his suggestion was refreshing. I don’t know many men who like to talk on the phone.

We picked a park so as to be careful with COVID. I learned that Aidan would be commuting about an hour to meet me. I was impressed and felt flattered.

When I first met Aidan, I thought that he actually looked better in real life. I was not expecting him to have such a great physique. He was wearing a nice sweater with dark jeans. We decided to walk around and try to find a patio.

Aidan seemed like a really kind and genuine guy, but I noticed that he didn’t ask me many questions about myself. I would ask him a question, he would answer and elaborate, but wouldn’t direct a question back to me. I would basically divulge information about myself without being asked. It got progressively colder and we were both shivering. We hugged goodbye. I left feeling like I wanted a bit more time with him. I messaged him that night and asked if he would like to go out again, and he agreed.

We decided to brainstorm ideas for a possible indoor date because it was getting so cold outside. I thought an art exhibit would be a good idea and he agreed.

The exhibit we went to was well-organized and designed for safety. I was relieved from that perspective. However, as I suspected from the first date, Aidan was not really an inquisitive person. We stood in silence beside each other at the exhibit. I was really trying not to carry the entire conversation, to see if he would ask me questions, but he just didn’t. I was cringing on the inside. It probably didn’t help the conversation that we were both wearing masks, and didn’t have the opportunity to experience and discuss the art in a normal way.

We walked around outside for a bit after, looking for somewhere to have a drink, and found a patio with a heater. The conversation was fine, but there were stretches of silence that Aidan didn’t attempt to fill and I felt panicked to talk. At one point I asked him a question and took a long sip of my drink to allow him a moment to pose the question back to me. It was crickets … Silence. I was shocked that he couldn’t ask me, “How about yourself?” Or even bring something new to the table. I realized that he didn’t know who I lived with, what I studied at school, what I do for work, what I’m looking for in a relationship or where I’m from, while I knew all of that about him.

Aidan was not conceited, the way some guys who don’t ask questions and are all about “them” are, but maybe he was immature or clueless. Either way, I am unwilling to babysit someone I’m supposed to be dating.

We left the patio and I hugged Aidan goodbye. I had no intention of seeing him again.

Erica rates her date (out of 10): 2

Meet someone cute at a pre-COVID company holiday party? First date on skates? New Year’s Eve proposal? Send your seasonal dating stories to [email protected]

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