He made me feel special, but left out one big detail

The daters: Brooke and

Charles

Brooke says: “At the time of the date, I had been taking a much-needed break after my previous relationship, which ended messily.” She adds, “I am now very selective about potential partners. I went through a phase of ‘open to whatever,’ where I ended up meeting some kooky people who treated me quite poorly. I now believe in quality over quantity.” Brooke wants “to connect with someone on a deeper level” and is looking for someone “who is genuine, and compassionate. I want someone who can challenge me intellectually and emotionally. I really enjoy thought-provoking conversations, and don’t mind dating someone with a very different perspective.”

How we met: Online

Where we went: A golf club

It all started with an experiment with a friend. We were both going through dry spells, not meeting anyone interesting, and decided to expand our age range online all the way to 60 just to see what would happen. I was in my late 20s at that point. Charles’ profile caught my eye. There was something intriguing about his warm smile. He was in his 50s and had a corporate job. I felt excited about the possibility of meeting someone who was so different from my previous dates.

“He took the initiative”

We had a surprising amount in common, despite the age gap, and there was a depth to our first interactions. He took the initiative and suggested we go out for dinner. It was a pleasant surprise, because usually I was the one making the first move.

Charles invited me to have dinner at his golf club, which intrigued me because it was so different than any other first date spot I had ever been to. He suggested we meet at his house and he would drive us there. I was coming from downtown. When I finally got off the TTC, his quiet suburban neighbourhood felt like a different world.

Charles shook my hand and complimented my outfit. He was chatty and witty. He guided me into a sports car. He kept pointing out different features. Gushing over the car was a bit of a turnoff; it seemed goofy.

I was curious about whether he had a family, as it seemed like a strange place for a bachelor to live. I wasn’t confident enough to ask that question and I was pretty quiet during the car ride.

“I felt a bit out of place”

The club was breathtaking, with rolling green hills against the setting sun. Charles had a charming way of making me feel attended to. He asked about my life, friends, roommate and even my way of dressing. I don’t think I’ve ever been on a date where he was so focused on me.

Despite all that, I felt a bit out of place. No one there really felt like a peer except for some of the staff. Almost all of the other diners were much older than me, and I felt like the odd one out. There were also moments when the generational differences between me and Charles became apparent, especially around politics.

I liked that Charles didn’t have an opinion about every single thing. I don’t mean to say he wasn’t opinionated — he was — but he was not afraid to say “I don’t know much about that. Tell me more.” His humility and curiosity fascinated me.

“Our peaceful moment was interrupted”

After dinner, Charles invited me back to his place for a nightcap. He poured us both a glass of wine. I felt like I was having an exciting, intimate conversation with a close friend. However, our peaceful moment was interrupted when his daughter walked in, catching both of us off-guard. I had no inkling that Charles even had kids.

I felt unsettled. As Charles introduced us, I could sense his own flustered state, trying to explain the situation to both his daughter and me. She was in university and was just stopping by to pick up some things.

“I just wish the details had come up earlier”

After his daughter left, we talked a bit longer but when I finished my drink, I checked the TTC schedule and got ready to leave. Later, over text, he opened up to me. He had been divorced for about a year. I could sense the love he had for his family, but I just wish the details had come up earlier. I’ve been on dates with people who had kids and it was always communicated early on. Most people put it in their profile. I didn’t understand how he could obscure such a big part of his life.

We continued to text a bit but things fizzled out. I took something with me from the date, though: Charles treated me really well. His kindness and attentiveness felt special, and informed how I expected people to treat me from then on.

Brooke rates her date (out of 10): 7