Read some of our WORST DATE Contest Entries!

Congratulations to the winners of our Worst Date contest! Brought to you by Crescent Gold & Diamonds, your OMG specialists and the Rock of the Rock, Newfoundland’s OZFM!

Check out some of our entries below and click here to submit yours! 

❤️ Worst date ever, went out to dinner and he threw up all over the table!

❤️ Back when I was 16 there was this guy that really wanted to date me and I was kind of putting it off cause he wasn’t really my type but anyway I finally gave in and agreed to go his house to watch a movie which I thought was harmless enough …well I arrived sat down and he left the room for a minute and came back completely naked! Safe to say I got out of there as fast as I could told him I wasn’t feeling well.

❤️ My boyfriend, at the time, picked me up in his parent’s car to head off to a movie. We got about 200 meters up the road when the car broke down. My boyfriend seemed a little confused because he knew there was a full tank of gas put in the car that morning. I watched as he got out of the car and opened the trunk to check the gas tank. I was really confused. The gas tank should not be in the trunk of a k-car! My boyfriend got back in the car with a silly grin on his face, he apologized for breaking down and confirmed he had indeed broken down for lack of gas. You see, his dad was a man of many talents and could “jimmy” anything together, including a gas line to an outboard motor gas can in the trunk of the car! This allowed for use of the car while the car’s gas tank was being repaired. BUT my boyfriend’s dad had taken the gas can from the trunk of the car to go for a boat ride! My date at the time turned out to be my high-school sweetheart, the love of my life and my partner for the last 39 years!

❤️ We met on Plenty of Fish, after chatting for a few weeks we decided to meet and she invited me to her hometown to go on a hike on a hiking trail. I showed up in flip flops. It was a very muddy trail and I had no hikers so we didn’t get far. It was the worst feeling. I thought I blew it for sure. It was the worst first date, however it was also my happily ever after. 6 years later we’re still together and I am always prepared for her adventures. She hasn’t let me live that one down!

❤️ My worst date was in 1980, I was going out in a nice, old Cutlass Convertible but he ended up taking me to the dump to watch the rats!

❤️ The first date, the very first time meeting, he suggested going to his work Christmas party, followed by supper at The Sprout and dessert at The Keg. We went to The Sprout first. Looking forward to eating, I was shocked when he ordered 2 small tacos – 1 for each of us. At which point he said he forgot his wallet in his car. I waited until he returned with his wallet. The tacos were less than 20 dollars, including tax. At his work Christmas party, he completely left me alone. Talk about being uncomfortable! I gave him the benefit of the doubt and we headed to The Keg. Unbeknownst to me, I was the payee for this portion of the “date” – He proceeded to order the most expensive dessert on the menu; and when the server asked if there was anything else, he ordered a coffee too! He then proceeded to say, I got the tacos, you can get this. Shocked and wanting to leave asap, I paid and hurried home.

❤️ Me and my date were hanging with some friends, he tried to kiss me and I literally DUCKED to avoid it. He was brining me home and in a rush because he was still on the 12 o’clock rule, and it was 5 minutes to 12- and he lived 20 mins away… He reversed into my Dad’s new jeep. Safe to say he didn’t make it home in time. Good thing his dad owned a rental car company. I think we went on one more ‘date’ and I had to break it off.

❤️ It was my birthday weekend. I was turning fourteen. […] My crush asked me out and we went for a romantic walk – a lovely casual stroll through the wooded trails near his house and it was going so well! We were laughing, chatting, and then, we reached a bridge. A picturesque little wooden bridge over a stream. Very romantic. And then—THE KISS. My first EVER kiss! And oh, the emotions! The butterflies! The life-changing moment until I DISAPPEARED. Apparently, the rain had been eroding the side of the bridge for days – a perfect little trap laid out SPECIFICALLY for my romantic downfall. So there I was, flailing, submerged knee-deep in freezing water, desperately trying to scramble back up the mud-slicked embankment like some kind of Bambi-on-ice. My date doubled over in laughter and I was absolutely mortified. First kiss ruined. But hey, at least I got a good story out of it!

❤️ When I was 19, almost 20 years ago now. I was invited to go to Woods Island on a first date. Just before dark we decided to go for a walk. Which turned into a nightmare and a 4 hour walk as we ended up lost walking in the woods. It was four hours and it seemed like eternity. It was so dark, thankfully not cold. I remember wishing I wasn’t there. Thinking I would never get back to the cabin. I knew then why the called it Woods Island.

❤️ When I was 18, living in Alberta, I went on my first date with a guy who I only hung out with a few times. The day he picked me up, I went to get in his truck, and he told me to take my boots off before I got in…. so I opted on not going and instead he asked if we could watch a movie at my place. I was hesitant but agreed, feeling I had already embarrassed him by not getting in his truck. But before the movie was over, he got down on one knee and asked me to marry him, needless to say the date ended once I told him to get up and get out!

Happy Valentine’s Day from OZ FM!