Sadie and Shawn
Sadie is a 29-year-old communications manager who lives on the west side. She says “My style is ‘trendy on a budget.’ I love a good deal. I’m a yogi wannabe, but at work and on dates I ditch my Lulus.” Sadie is “bubbly. I’m always willing to help other people, and I try to keep learning new things. I’m always reading, and I love hiking, eating and travelling.” Sadie has been single for a few months, and describes her dating life as “somewhat active.” She says “I want to date someone I can have fun with, someone who is adventurous, caring and sweet. Good looks are a perk.”
Shawn and I met online. He followed me, and I received an email notification. He was cute, so I followed back. We started communicating by making random comments, back and forth, and then moved on to messaging each other. We discussed favourite authors and books, movies and TV, and work stresses and achievements. We talked about family life — he was still living at home, which sounded alarms for me because of his age (early 30s), but he seemed confident and mature — and what we liked to do in our free time. Our chats were really candid, and Shawn was really smooth. I developed a crush, for sure. After a month of flirtatious banter, we decided to meet in real life.
Since Shawn and I lived about an hour apart, we rationalized that we should make the most of meeting in person, and spend the day together. Leading up to the date, we continued to chat daily, just a few sentences at a time.
The highly anticipated day finally arrived. I was going to meet the guy I liked! I wore a cute new top, and Shawn was right on time. We awk- wardly hugged as we said our hellos and then he led me to his car, as our day-date checking out some wineries required driving. Was it love at first sight? No. I found myself looking at his dishevelled hair — and his receding hairline, which I hadn’t noticed in his profile photo — and his outfit: a polo shirt tucked into jeans, and faux-snakeskin shoes. The look was “preppy-nerdy,” but trying too hard to be cool. This was off-putting because my type is more “hipster-vintage,” which Shawn was not. He did have a nice smile. I wondered what I had gotten myself into.
There was some nervousness between us in the car. He was polite, easy to talk to, and kind, but there was no physical attraction on my end. He mentioned his excitement about finally being able to try the “new releases.” I didn’t know what he meant, and was too embarrassed to ask, but then realized he was talking about the wine.
While swirling, sniffing and sipping our way through shared wine flights, Shawn kept asking what I smelled, what I tasted, and what I thought. After giving him the same “I like it” reply over and over, and continually being urged to elaborate, I wanted to scream “Do I need a reason, can’t I just like it?” He had a lot of wine lingo up his sleeve, and I was mortified when he used it on our servers. What was this guy saying?
After our wine-touring rendezvous, and with an hour to spare before our dinner reservation, we decided to go for a walk. Shawn proceeded to grab my hand, and after I pulled it away to scratch an invisible itch as a subtle hint, he tried again, and then again. I finally gave in and let him hold my hand as we walked. He seemed completely oblivious to the fact that I wasn’t into it. I don’t think he had much experience dating prior to this date.
He had booked the chef’s table at a restaurant, where his wooing efforts continued with an absurdly priced bottle of Champagne and a multicourse meal. The bubbles were perfectly delicate, the food was delicious, but in the dim lights of the five-star restaurant, I couldn’t see a second date.
Back at my place that night, I realized that Shawn had assumed he’d be staying over — he had an overnight bag in his car! I agreed that he could sleep on the couch. He seemed happy with that and said it was no problem. He actually seemed excited at the notion of our date being neverending, and pulled out a DVD that he’d packed, as well as a bag of homemade cookies his mom had baked for us.
He sent a stream of messages the next day, which then slowly started to dwindle. I’m embarrassed to admit this, but I ignored all of them. We haven’t talked since the date. Sadie rates her date (out of 10): 4 Want to be a dating diarist? Email datingdiariescontact@gmail.com