Magical first date a decade after first meeting
Sandi, 31, was swooning after wandering Yorkville’s streets holding hands with Cedric
Sandi is a 31-year-old advertising executive who lives at Yonge and Bloor Sts. She says “I ‘stalk and shop’ sales at Holt’s, TNT and Nordstrom Rack and buy well-made basics that will last for years. Even my casual clothes are deeply discounted designer pieces.” Sandi likes “looking at Pinterest and Houzz for decorating ideas; meeting friends for exercise classes; going out for drinks after work; checking out summer music festivals; and spending weekends in Muskoka” and says “I take part in the Yorkville social scene, but I’m just as happy to stay home and enjoy my condo and my building’s amenities. I spent a lot of time decorating and making a ‘clean, calm and classy’ space to relax in.” Sandi has been single for two years.
Cedric and I went to college together. We met more than 10 years before our date. He was part of a different social group, but I always thought he was so cute. We ended up in the same industry and kept track of each other over the years. We sometimes messaged back and forth on Instagram. One day, out of nowhere, I decided to see how he would respond if I took it a step further and sent him a flirtatious message. That led to him asking me out.
He took the initiative to make dinner plans at one of the best restaurants in the city. I was out of town for business and didn’t get home until just two hours before our reservation, so I flew into action and worked out, showered, got dressed and did my hair and makeup. I was ready for a first date that was classically romantic and hopefully a lot of fun.
Cedric was seated when I got there. He looked amazing. He seemed a bit nervous, but I was nervous too. I covered it up by exaggerating a bit about how I’d gotten back from my business trip just before dinner.
The conversation started a bit flat, but I focused on being as charming as possible. Cedric relaxed and the conversation took flight. We had a lot to talk about between our industry and the different groups of people we knew. It turned into an incredible conversation. It was very intimate. We were laughing and getting close in the candlelight. We drank a lot of wine, and I was feeling the effects because I was so tired from travelling and too nervous to eat much in front of Cedric. We shared a dessert.
He paid the entire bill. When we walked out we were past tipsy and officially drunk. I didn’t know if I should invite him over to my condo or if we should go somewhere else for a drink or just leave it at that, but before I could suggest anything Cedric took my hand and started walking.
We wandered the streets of Yorkville. It was so romantic. The streets were full of shiny people spilling out of bars and restaurants. It was so nice to be there, holding hands with Cedric.
After a while, Cedric and I sat down on a bench. We were giggling. He kissed me and I kissed him back through a smile. It was going so well, it was like a fairy tale. Then I heard a voice, and looked up.
There was a homeless-looking man standing there, looking right at us. He started to talk to us about something and it seemed like he wanted something, but I didn’t know exactly what. I do volunteer work almost every week for a charity that helps the homeless, and if Cedric and I weren’t sitting there drunkkissing at the end of a nearly perfect first date I would have talked to him and given him money, but on the date I didn’t know what to do.
Eventually the man walked away. I felt bad that we hadn’t helped him. I looked at Cedric and he seemed confused and like he hadn’t known what to do, either, at least. The spell of the magical date was broken. It did help me to sober up a bit.
Cedric walked me to my building and we kissed again. It was nice. We decided to go on a second date. I hoped it would have a better ending than the first!
Sandi rates her date (out of 10): 8 Want to be a dating diarist? Email datingdiariescontact@gmail.com