Maggie is a 43-year-old entrepreneur who lives in Queen West. She describes herself as “a sexy brunette” and says “I’ve started to dress younger, more daring. I love a statement jacket or even a statement hat.” (She adds “My hair gets bigger and more unruly in the humidity.”) Maggie says “I’m comfortable everywhere: in the boardroom, on the dock at the cottage, at karaoke. I can also talk to anyone about anything.” She is “well-known for my honesty and oversharing” and says “I have a wicked sense of humour, and almost no boundaries.” Maggie’s friends and family make her feel fulfilled, but she says she would like to have “one special man” in her life.

Out of the blue, I got a message from a man with very little on his online-dating profile. No pictures, and almost no information. He included some compliments on my profile pictures, and references to things we had in common. He also said he was tall and athletic and would share pictures if I wanted him to.

I gave him the email address that I use just for dating — no last name! — and said I’d welcome pictures. Shortly after, a big smile stared out at me from my phone. He was so handsome that I decided there was no reason not to reply.

That was the first dating rule I broke with Dennis: engaging with someone without sussing out the basics of who he was and what he wanted. He could have been married, looking for hookups, or live too far away. But I figured the randomness of his outreach was almost reason enough to see where things could go. Plus he was so handsome. We exchanged a few emails, and I gave him my burner phone number so we could text.

On the first call, we talked for over an hour. We spoke again, and again, and again: more than 10 hours in total. Like a lot of women, I don’t like to spend so much time engaging with someone before I meet them. It’s too easy to get my hopes up, just to discover there’s no real chemistry.

We agreed to meet close to my place on a weekend afternoon. I told him he could park at my house. That’s another rule I broke, that a lot of women abide by: never meet someone for the first time where you live. But we did. Dennis had given me his name and birthday, and I’d independently confirmed that he was who he said he was.

When I opened my door my first thought was that he really was as tall as he said he was, quickly followed by the thought that he’s even more handsome in real life than he was in the pictures. I had planned to take him on a walk around my beautiful neighbourhood. I knew we would have dinner back at my place, if we were getting along after the walk. And we’d already talked about our views on first-date sex.

Dennis arrived with a small gift bag. Knowing I’d had some recent, unusual-for-me stresses, he brought me a great selection of chocolates. I was impressed. A bottle of wine or flowers is nice, but standard. This showed he’d been thinking about me.

Before we left for the walk, we sat on my couch and talked. He was affectionate. I liked it. When we kissed, it was good. The conversation flowed just like it did on the phone.

We realized a game was on TV that we were both interested in, so we turned it on. This was something I would never do on a sixth date, let alone a first. We talked and occasionally turned our attention to the TV when something exciting happened. We got a bit more heated, but would take breaks and talk. Between the baseball and the make-out session, we abandoned plans to go on a walk.

However, I soon realized I was getting a migraine. They often hit with no warning. I took my usual medicine and waited for it to take effect. He was very understanding.

I sheepishly told Dennis that sex increases blood flow, which sometimes helps migraines. At the very least, it would distract me. All of my first date rules were now officially thrown out the window.

Although I lose my appetite during a migraine, I knew he was hungry. I was in no condition to leave my house, so Dennis offered to pick something up for us. I ordered from my favourite restaurant, and he picked it up and paid.

I liked a lot of things about him, obviously. But what I liked the most was his willingness to have an unusual first date.

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Maggie rates her date (out of 10): 7