When Harry met Phoebe
After the AGO, we wandered to a nearby bar. We said cheers to a good first date ‘so far,’ and laughed
Phoebe is a 36-year-old product manager who lives in Roncesvalles.
She says “I keep it girly-ish: I have long hair and usually have my nails painted.” She says “My people would describe me as fun, social, bubbly, and a closet intellectual.”
Phoebe says “I was a bit of a serial monogamist in the past. I got married young.”
She is “open to meeting someone ‘special,’ but I’m not banking on it, or expecting ‘the one’ to stroll in.”
She is looking for “someone who seems like they might be smarter than me. Maybe someone who loves to play Scrabble. And I’m a sucker for a kind smile.” I met Harry on a dating app. He’s tall, has dark hair and eyes and shared some really random photos on his profile that were bordering on just ridiculous: hilarious, not in any way flattering, really weird and different.
I’m so over guys who are shirtless in pics. Like, yeah, get over yourself.
Harry was totally inconsistent with the types of guys I’ve dated in the past. He was younger than me, and wasn’t a professional.
We immediately found things to joke about. I found myself smiling when I read his messages. I liked him, and when you’re dealing with a lot of messages from different guys, it can be tough for someone to stand out.
I ended up asking him out. I said something like “This is great and everything, but maybe we should meet and talk in real life.”
I had sworn off drinking for a month, and had already had a pretty miserable first date around then, when I’d ordered San Pellegrino and the guy ordered alcohol and seemed to judge me for not drinking.
I asked Harry if he wanted to check out an exhibit at the AGO. He seemed really happy that I’d suggested something different.
I was late and I hate being late, so I was a little flustered arriving at the AGO.
When I walked in, Harry gave me a hug. He was a total babe and had the longest eyelashes I’ve seen on an adult. After helping me with my coat, he told me that he had taken care of the tickets so we could avoid the lineup. It was a good start.
We joked about how I should take a pic of one of the hideous creatures on display and share on social media that this was my latest online date.
Harry had a good balance of being sarcastic and funny, and thoughtful and pensive. There was a room full of comic books, and it became pretty clear that he knew a lot about them, and it felt natural to playfully lean into him when I teased him about it. Then, there was a moment when he touched my arm to get my attention. After that, we took the small opportunities for physical contact, always in a non-creepy way. Two hours had passed when an announcement came on, saying that the gallery was closing. I was so disappointed. I’d been having fun.
I was prepared to leave it there, but Harry asked if I wanted to get a drink. The way he asked surprised me, admitting that he was having a great time and wanted to keep talking.
I’m used to playing it a bit cool, or the guy playing it cool. Harry was just doing what he wanted to do. I hesitated, because I’d been doing so well on my cleanse, but I really couldn’t help but say yes.
We wandered to a bar nearby. We said cheers to a good first date “so far” and laughed. After breaking my pledge to not drink, I told Harry about it and it was clear that he felt badly. I reassured him that I was happy to get to hang out with him more.
We talked about what led each of us to Toronto, how he got into his career, how my corporate-ladder climb is going. One drink turned into three and about three more hours.
I don’t kiss on the first date as a general rule, but all I could think about was how much I hoped he would kiss me.
It got late. The conversation was still going strong when I said I needed to call it a night.
Harry asked to walk me to my streetcar, and as we got to the stop, a streetcar approached.
The first moment of awkwardness happened then, as Harry said he wasn’t sure if he should kiss me, but really wanted to, and then pulled me in and gave me a sweet kiss. It was clear there was chemistry, and even clearer there would be a second date. Phoebe rates her date: (out of 10): 10
“We immediately found things to joke about. I found myself smiling when I read his messages. I liked him, and when you’re dealing with a lot of messages from different guys, it can be tough for someone to stand out.” PHOEBE
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