Abby and Jonathan
Abby is a 29-year-old woman who works in IT and lives on Dundas St. W. She says, “I’m into politics, and am closely following the election.” Abby describes herself as “philosophical,” “goal-oriented” and “warm, but only with people I like. I have to admit that I hold myself and others to a high level of social standards.” Abby likes going to see live music, reading and learning new languages and about other cultures.
Oscar Wilde said, “With age comes wisdom” and I’ve always agreed. But it’s not like the idea of dating younger men has never crossed my mind. Especially now, with everybody from Madonna to Jennifer Lopez doing it. Even my mom once had a younger boyfriend. It might not be the new normal, exactly, but I felt like I might be missing out. I decided to take a chance on Jonathan, who I met online.
Jonathan is only four years younger than me — not a huge difference — and he was sweet, attentive and romantic in his messages and texts, not to mention super cute in his pictures. It also felt incredibly serendipitous that his profile listed some of the exact same things as mine. For the first time, I truly believed my days of online dating might be over.
We live in opposite ends of the city but, for Jonathan, that was hardly an issue.
In fact, he wanted to drive across town to pick me up after work and get dinner on our first date. I was impressed by his show of commitment and thrilled to finally meet him in person after a lot of texting.
The night of our date was unexpectedly cold. I didn’t dress entirely appropriately and the short walk from my office to his car — he was parked around the corner — was unbearable.
I was so excited to meet him, until I slid into the car and saw how he came dressed for the evening. Jonathan was very cute, but he had driven across the GTA in a cold snap in nothing more than a white T-shirt, basketball shorts and a baseball cap. He just laughed and said he’d forgotten to change before the date. I wondered why he hadn’t worn even a jacket — or pants! — but mostly wondered where he was planning to take me in that outfit.
We ended up at a cosy pizza restau- rant nearby, which was fine. However, his summer attire drew attention from everybody there. Jonathan didn’t seem to notice. I tried not to focus on it and stay in the conversation we were having.
It was a little awkward, but nice, and both of us were trying hard to be entertaining and present. He didn’t check his phone or make inappropriate jokes like a lot of guys I’ve dated who are significantly older — and apparently less mature — than he is. So far, pretty good.
Back in the car after dinner, Jonathan told me he was going to play me some of his favourite music. It was awful. He played it loudly the entire drive home.
I silently scolded myself for not being more open-minded about his taste in clothes and music, but also felt that a good date would not involve being a captive audience for someone’s favourite band, with the volume turned up all the way, no less.
Despite the quirks of the date, I decided I liked Jonathan. He was kind, fun and did I mention cute? By the time we got back to my place, I had decided that I would give him a chance and that the effort he had made at dinner suggested he deserved a second date.
I usually don’t kiss on a first date but, for him, I made an exception. It was nice and quite sweet. I got out of the car and, when I went to bed, I was feeling like I was finally starting a new chapter in my life. Maybe Oscar Wilde had it wrong.
Then again, maybe not. In the middle of the night, I got a call from Jonathan begging me to let him come over again so we could have sex.
He even started whimpering. It was so disappointing and slightly gross. That’s when I remembered why dating younger men isn’t always the best idea and hung up the phone. Abby rates her date (out of 10): 6 Want to be a dating diarist? Email datingdiariescontact@gmail.com