We asked readers to share their most romantic, hilarious, scandalous or just plain awful first date stories for a chance to win a $200 gift certificate to Entice Culinary Lounge this Valentine’s Day. After selecting our ten favourite stories, we did a random draw to select the winner.
Congratulations to Kevin on being our grand prize winner! Read his story below:
My first date was when I was 13. My mother drove me to pick the girl up and drove us to the movie theatre. Then my mom picked us up afterwards and since it was a matinee she then drove us to the park near the end of my street and gave me a filled picnic basket and told me to take my date for a picnic. My mother then went home and we sat in the park for an hr or so before I walked my date home. Then I went home and my mother never asked or said another word about the date again. The girl I was on the date with was 16 so we only saw each other a couple more times until she found someone who could drive their own car.
Special thank you to everyone who submitted a story. The entries were so good, we had to share some of our favourites:
The first date my husband and I went on was to Dairy Queen. I bought him a vanilla and chocolate swirl soft serve cone and he told me he really liked me.Twenty years later we go back to that same Dairy Queen and I buy him a cone every year on our anniversary. – Diana
Being a very bookish person, I usually date fellow reading enthusiast. Last year, I tried dating guys outside my “type”. This lead to my getting coffee with a young man who boxed. It was fine until he started talking about how much he absolutely loved everything about boxing. He was very proud of how his biceps developed during his workouts. He flexed, and then kissed them. I asked, jokingly, if they had names. They did – Rosencrantz and Guildenstern. After that, I knew I had to get out of this coffee date asap. Saying that I needed to get going, he offered to walk me home. He ignored my insistences that I did not need an escort and walked me home. I guess he was trying to salvage the date, but when we arrived at my door, he planted a giant kiss right on my mouth. I said bye and ran into my house. He texted me a few minutes later saying I was a good kisser, and that Rosencrantz and Guildenstern agreed. I almost threw up. A year later, I’m still grossed out by the story. – Rachel
My first date experience was also my first concert experience! I was about 16 (so over over 30 years ago). I am 49 now!!! I was working in a restaurant as a hostess and a co-worker asked me to go to a Pat Benetar concert. We met at Victoria Park subway station and travelled on the TTC. I don’t remember the exact location of the concert but it was in downtown Toronto. We had a very nice time although it was a little awkward (being a first date) but it was something I never forgot. – Alexandra
I think one of the most memorable, stressful, and awkward first dates for me took place when I was a young teenager. I was being bothered to go out with a guy for a long time and was never really all that interested. We had some friends in common and so we started spending some time together. You could feel the curiosity and interest building. After a few weeks he finally asked me out. He invited me over to his house (his parents were going out) to hang out and watch a movie. When I got there it was quite tense. Lots of tension and nerves. The talking was brief and so he suggested we sit on the couch and watch a movie. Sounded pretty normal…except that the movie turned out to be the infamous Sharon Stone feature ‘Basic Instinct’ which starts with a pretty intense sex scene. A-w-k-w-a-r-d! This made for one of my most memorable, and awkward, first dates ever. – Aphra
The best was when my date had to run out because… and I quote….”my wife is having our baby!” and then proceeded to text me after to set up a second date. Safe to say I declined. -Vanessa
On our first official date my now partner in life took me to a fancy restaurant in Burlington. It was the summer time and before we entered the restaurant there was a sun-shower which is one of my favourite things. There was a waterfront event happening next to the restaurant, so we strolled on the boardwalk. He bought me a $10 ring at a vendor which I needed to keep another ring in place – it was also my birthday. This became my promise ring and was later engraved for another $5. That night there were also fireworks and he told me that he had his people set that up special for this date. As the fireworks came out of cannons set up in the distance on a boat, I fell in love. – Dorina
During university I managed to get a fantastic apartment in a large 18th century home. My bedroom was 380 square feet with a fireplace. It was January, winter semester had began and I had met this groovy girl in one of my intro biology classes. I invited her back to my place for a home cooked dinner and hot chocolate by the fireplace. I had never used a fireplace before but I thought how hard could it be. The night of the date we had a nice meal and I lit some wood in the fireplace. We were enjoying the glow and warmth of the fireplace, chatting and sipping on hot chocolate when she remarked it was starting to smell smoky. I agreed and got up to turn on the lights. When I did we saw the room was filled with smoke! I didn’t realize that you had to open the flue so the smoke was billowing back into the room. She quickly stood up and said her eyes were burning so I shooed her out of the room and opened all the windows. It was our first and last date, but makes for a great story. – Robbie
I had a date with an obsessed ice cream lover. We went out for dinner and for desert she ordered a huge banana split and devoured the entire thing. As I drove her back home she asked if we could stop in at . . . you guessed it, Dairy Queen so she could get some ice cream. That was also inhaled in record time. When we reached her house she said that her roommates had some friends over for a small party and asked if I’d like to join them. I don’t know if it was out of curiosity or what I was thinking, but I obliged. She went straight to the freezer and took out one of those enormous tubs of ice cream, asked if anyone wanted any, everyone said no and she sat down in front of the TV with it and ATE. THE. WHOLE. THING. We didn’t have a 2nd date, I knew I couldn’t compete. I’m now married to a woman who doesn’t care for ice cream! – Andrew
Bad first date story – In fact, it isn’t even a bad first date, because it didn’t end up happening – it was a bad attempt at a first date, and worse, my first attempt using Tinder. I ‘swiped right’ with a guy and chatted to him for a few days. I mentioned wanting to learn golf, and he suggested we go to a driving range for our first date. We set a date for later in the week, and I gave him my phone number to text me. After messaging constantly early in the week, first date day arrived. Curiously, I hadn’t heard from him, so I messaged him to see if we were still on. Surprise, surprise – no reply! Later that day, I went on to my WhatsApp to message a friend, and his contact/ picture popped up. Well, wasn’t I surprised to see that his WhatsApp profile picture was a lovely picture of him – and his girlfriend! It sure did explain things. – Caroline
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