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Worst date? Best date? Share your stories

Sat in awkward silence or danced until the lights came on? Charming bistro dinner or peculiar pickled eggs? Share your best and worst date stories (instead of reading ours). Comment in the field below - We'll publish our favourite stories on Valentine's Day

  • Blind date showed up in all leather, wearing a 'recreational' eyepatch. Obviously my friend called and something 'really bad happened.'
  • While waiting for a supposedly very handsome man and standing by the perfume counter looking for a sensual scent, I was telling the salesperson that no man could look as good as the pictures he had sent me and that he was probably overweight...well little did I know, he was standing 2 feet away from me, extremely handsome and smiling...the salesperson laughed and said one word: Oops!
  • I could smell him from 10 feet away. We met outside a bar and I could smell him before I knew it was him. Bad start. It was very crowded and loud bar after a CFL game; we didn't know about the game, so it was bad planning. We agreed to meet at a quieter place where we could talk. He kept me waiting inside the bar for 20 minutes; I thought I was being stood up. Turns out, he waited for me outside. But he waited not outside the main entrance, which I could see from my seat, but outside the back one! He finally came inside and we ordered drinks. When the glass I was drinking from broke, he neither offered to help me clean up nor went to get a staff member to help me clean up. He just watched and kept talking about himself.

    Although he knew I was a server myself, he stiffed the waitress, even though she comped our drinks, helped me clean up and dry myself and apologized profusely. I couldn't let that go, so I went to tip her. As I did, my purse spilled and he didn't help me pick up my stuff, he just stood there. At this point, not only I, but the other customers were just stunned. And giggling. I went home. When I got there, I had not one, but THREE messages on my voicemail about how rude it was to stand someone up, which, he never bothered to share with me that he left.

    Just as I was getting into the well-deserved hot shower, the phone rings. It's 11:30 at night, and, you guessed it! It was him! Telling me what a great time he had, and could we do it again tomorrow? Um, how about NO?
  • Why are all the stories bad? Doesn't anyone else have a good first date story? OK, I'll share mine:

    We were both 19. We had known each other at university for three months. She was from a small town, and I was from the big city. I was intoxicated by her sweetness and innocence, so I summoned every bit of charm at my disposal, I swept her off her feet, took her on a whirlwind tour of Toronto's downtown, showed her the sights, put stars in her eyes, and won her forever. It's now 23 years and two kids later, and we're still together, still holding hands in public, still in love. And she still counts that one night as one of the highlights of her life.

    A good first date is not just some trick to get a woman into bed: it's an opportunity to give her an experience she won't forget: to show her something different, and set yourself apart. I took her for a short ride on the subway that night, and you might think "The subway? That's not romantic". But SHE had never ridden one before, and that's the whole point: the experience has to be something memorable for HER, not you. If you know what you're doing, anything can be romantic.
  • So I was meeting up with a guy from a fraternity at UofT to pick up some... er... study notes. I had met him a few times before, but this was our first time hanging out alone. We studied at his frat house for a bit, then he decided to accompany me home. We were having a good time chatting it up, and the chemistry seemed to be flowing as well. He tried making the moves on m, and I let him know he wouldn't be getting THAT lucky. Eventually we got hungry and decided to go out for sushi at NewGen. He ordered a ton of food, and I settled for a roll. At the end of our 'date', he told me he had no money and asked if I could pay (I asked him why he ordered so much, and he said it was for us, although I never had a bite).
  • The best part came at the end; When we got outside, he asked me for 3$ for bus fare!!!
  • Best date: My husband and I met in Havanna, Cuba, while I was studying at the University of Havana. It turned out we were both from the same city in Canada. Our first date involved hanging out on the Malecon (sea wall), and heading to the Hotel National, where we sat on the bench and watched the ocean. It was a simple date, but I thought "wow, if I can sit on a bench with this person, in silence, and feel totally at ease, then he's the one for me." Five years later, and we're still going strong!
  • MY first and ONLY date with this guy started with him making fun of me for waiting outside the restaurant where we AGREED to meet....it gets "better". He was rude to the wait staff and the chef who was cooking our food in front of us. When we started eating, he showed me the "right" way to hold chopsticks...uh, huh. My questions ( conversation starters ) were answered with one or two words...no questions for me....
  • "Blind date showed up in all leather, wearing a 'recreational' eyepatch. Obviously my friend called and something 'really bad happened.'" -- men and women are different, I guess.
  • He also told me that he normally dates "really beautiful women....He emails me the next day ( because obviously I wasn't giving him my phone number ) and asks for a second date. All together now. "NOT A CHANCE !"
  • We had been seeing each other for a couple of months and I was definitely smitten. For Valentine's Day, I decided to take him out for a really nice dinner (think $300 nice !!) on my barely more than minimum wage salary. He picked me up with a lovely card and flowers. We had a wonderful time, and then he drove me home. At the door he kissed me on the cheek and said goodnight... Strange, I thought, but it was late and we both had to work early the next day. About 15 minutes later the phone rang. It was him, and he broke up with me over the phone! Did I mention we worked at the same firm ?
  • VD Horror, I know your monicker refers to Valentines Day, but the double entendre is irrestible.
  • First date with someone from online. He seemed so busy in his life I had no idea how he'd have time to date, but was a bit flattered he found time for me. However, a day-date starting at 9am Saturday was the only mutually convenient time. In advance, he told me he had all kinds of special surprises planned - I was excited! Sat rolls around and he is at least 20 mins late - hungover as all hell. Not just mildly - crippling. I had to accompany him to the pharmacy for gatorade chapstick and advil. He said he had planned to finish the surprises for me that morning but slept in. Ironcally, the only think he had managed to arrange were tickets to a cocktail exhibition even tho I said I didn't drink. Father of two, govt worker and aspiring lawyer - what a catch.
  • Certainly the most memorable. I was dating a guy who was already partnered. I knew they lived together but at that point not sure of their "status". So we went to this restaurant in Tokyo. Tokyo's pretty big, right? The staff seat us at a large table and we're having a good time. Who shows up at the restaurant? His partner/room-mate and HIS date for the evening. Doing what the Japanese do, the staff saw a number of white people and decided to put us all at the same table. Thousands of restaurants in a city of 12 million and they walked into ours. We all had a chuckle about it. We broke up, they broke up, but we're still on good terms. Actually, the 3 of us are.
  • Don't forget to include your name and city! Keep the stories coming: the good, the bad and the awkward.
  • For all of my years except one - and that's more decades than just a couple or a few - I have spent Valentine's Day alone. Dating in this age is tough enough, not to even say anything about getting to a relationship. So all I've ever known is that one Valentine's Day with someone special that will have to keep me inspired, hopefully just for now until it gets better. Till then, still a dreamer.
  • I went out with a guy last year who was two years younger than me. We got to the restaurant and he told me that his mother didn't approve of our date because I was older. I asked him how he felt about it and he told me that my "biological clock" was ticking so he wouldn't enter a relationship with me. Then we split the bill.
  • I went out on a blind lunch date. In the middle of the date, the guy reached into his nose, pulled something out. At my shocked reaction, he replied "oh sorry, that was bugging me, guess that's why they call it a bugger."
  • I only have bad date stories. Please please please - let's hear more happy date stories. I need hope! Online dating seems like a very shallow mine field. Where to meet responsible, happy, confident (single!) men in their 40s/50s who aren't looking for a super model?
  • We were both exchange students in Denmark. We agreed to meet on a Friday night in the city centre. But I misheard the location due to his accent and a bad cell connection... I waited almost an hour at the wrong spot! So I started walking around to figure out what to do with my evening and I ran into him. He was glad to have found me and know I didn't stand him up! I explained where I was and we had a good laugh. It was a fun night in the end.
  • First 'date' met at a Student Political Gathering at U of C, felt a connection, but part of the gathering was a big sleepover in the student centre. Both woke up at 5:00 am unable to sleep, so went for a walk around campus talking about anything and everything...really deep connection. We came from different backgrounds (small town vs. big city) but had a ton in common. Then went to go back inside because we were freezing, and the doors to the Student Centre were locked until 7:00 am, so we shivered in the doorway for nearly an hour, trying to get someone's attention on the inside. Turned out ok, we were married just over 2 yrs later, and are still together 19 years after that.
  • He arrived at my door with roses and a bottle of wine. This was particularly appropriate as I met him in the Vintages section of the LCBO (where he worked). We drove up to Chelsea, Quebec for a tour of an art gallery, then we spent the rest of the evening in the Market in Ottawa, sharing our stories with one another. I was shocked to look at my watch and see that it was time to go home. When he dropped me off, we shared our first kiss. Both of us walked two feet off the ground for days afterwards. That was in 2008 and we were just married this past October. It feels like the perfect date that has never ended.
  • He arrived at my door with roses and a bottle of wine. This was particularly appropriate as I met him in the Vintages section of the LCBO (where he worked). We drove up to Chelsea, Quebec for a tour of an art gallery, then we spent the rest of the evening in the Market in Ottawa, sharing our stories with one another. I was shocked to look at my watch and see that it was time to go home. When he dropped me off, we shared our first kiss. Both of us walked two feet off the ground for days afterwards. That was in 2008 and we were just married this past October. It feels like the perfect date that has never ended. --Sharon, Carleton Place
  • We were introduced by his roommate and we were both instantly drawn to each other. We went on twelve dates and he still hadn't kissed me. Fearing major halitosis or lack of interest, I confronted him and was shocked by his reply. He said that if he kissed me he knew he'd want to marry me and he had to make sure it was right. We've been happily married for 26 years now and he kisses me everyday. Vonda Ottawa
  • Online dating is like finding a needle in a haystack. I thought I potentially found a needle. We chatted non-stop (pictures, texts, phone) for two weeks due to prior commitments and single parenthood before meeting, and we both admitted we had hit it off. Got together one Friday night to watch movies and hang out. I said he could bring Star Wars (his fave) as I had not seen in a while. We chatted on and off throughout, had wine, snacks etc. After the first movie, I thought if he was staying that it was a good sign but I had no plans to watch the ENTIRE trilogy!! Yes, we watched all three. Never heard from him again. Seriously?!
  • Summer of 1950, Grade 11, new boy in town, made the Sr. Men's baseball team, won a leather jacket. 1 July 1950, had to show off my trophy jacket even if it was
  • @Richard G&M cut me off ... EOS
  • I`m a gay and ended up on a "date" with a straight guy once. ...My friend and his colleague insisted he was hot for me. He was certainly friendly and interested it seemed, but I was still uncertain about his sexuality. My friend said if i didn't ask him out, she would ask him out on my behalf and don't be such a chicken. OK, but I was never so nervous to ask anyone out in my life. "Would he like to go for dinner?" "Sure," he said. I was almost sick as I headed over to pick him up; guess my subconscious was telling me something. Anyway it turned out a disaster with him offended and me withdrawing from the dating game for a couple of years. It's still not funny (expect I'm laughing).
  • He picked me up and we went to a movie out of town. While waiting in line to pay he turned to me and asked "Can you get in for child?" I looked at him and said "Seriously?" He was too cheap to pay adult price for me (I was 16 at the time) so I said to him "I may look young but I DON'T look 12!" That was the first and last date with this cheapo. And the movie? "Star Trek".
  • My best date was a blind one : we met through a Web site, but that was wayyyy back in 1997, when most people were not necessarily exchanging pictures before they agreed to meet. So after many great emails, we decided to meet in a coffee shop one night. He said he would be wearing jeans and a black turtleneck. I got there early, and it turned out there were several people there wearing jeans and dark turtlenecks. One must have been 14 years old. Another appeared to be severely disturbed, or on crack. Another one... suffice to say, I was getting ready to leave, when yet another turtleneck-and-jeans guy at the counter turned his head and looked at me, and then I knew. I fell in love that night and we’ve been together ever since.
  • I met my current bf working a pub. He'd come in and I'd switch tables just so I could serve him. Eventually he took the hint of my flirting and asked for my number. We went on our first date a few weeks later and just sat and talked for hours, found out that his great uncle was best friends with my grandfather and we had met members of eachother's family a few times when we were young. We've been together for 4 years and are currently expecting our first baby...and we can still just sit and talk for hours.
  • I have an encyclopedia of bad date stories but let me share a recent online dating horror. Met this guy on one of the online dating sites - tall, handsome, an engineer, doing MBA - his pictures looked really good (so check, check and check)so I was quite motivated to meet him. After a week of chatting on bbm (a week of my life I will never get back unfortunately), we decide to meet up for a drink in Yorkville. He shows up and I was impressed that he actually is as handsome as his photos (as opposed to the guys that send you pictures of themselves under really "good lighting"). And then......he spoke...omg he had the voice of the homosexual hairdresser! I was horrified but thankfully the place had loud music. I stuck it out as I was trying to decide if his looks were enough to compensate for that voice. After a few drinks, he suggested we go dancing (yippee a place with even louder music!). We get into his car and as he pulls out of the parking garage, he takes out a bottle of vodka he had hidden under the driver's seat, pours the vodka into an empty starbucks cup and starts drinking WHILE driving. If things could not get any worse, he asks if we can pass by a bank machine. He pulls over and then starts to smoke a spliff!! Needless to say, I was not impressed and I had to put up with his incessant messages for weeks afterwards calling me "babe" and "sweetie" and asking if we can do the "wonderful" night all over again. He even started getting upset and accusing me of being "weird" when I would not reply to his messages!
  • Don't give up on dating online! I didn't and found a great guy and we just got married. After meeting for coffee in Yorkville, we went out after Thanksgiving in October 2010 on our "first date" golfing in Niagara and dinner at a Brazilian
    Steakhouse. It was a
  • Please be sure to include your name (first and last) and city - these stories are terrific.
  • Worst Valentine's day date: I was in a long term relationship for about 5 years. She went to the UK for school/work for one year, leaving in September. I visit her in Feb, we go out for dinner on Valentine's day and she proceeds to tell me about a guy she slept with a couple of times when we are apart. She didn't seem to get why I drank so much alcohol over dinner and ended up screaming at her just before the check arrived. I had to stay in the UK for another week. It gets better. I return home and within a few months I bump into an old friend from high school. We had been living in the same neighbourhood for years without ever bumping into one another. The UK girl hears about my new relationship, calls me and insists she is returning to Canada. I asked her why? She wanted to save the relationship. I laughed in her face and told her not to waste her money. A few months pass and I am engaged to the new woman, who I have known for 15 years. Within days of my engagement, the UK girl calls and tells me she is pregnant with some Brit's child. I wished her well and told her that I was getting married...there was a very long silence. It is now six years later, I am happily married with a 3 year old son. I have heard through the grapevine that UK girl regrets becoming a mother and is still working on her doctorate--year 8 going on 9. Funny how life works out sometimes.
  • I met a guy through an online dating site. We talked online for a while, then met in person. The date went alright, but there was no chemistry at all, so we didn't go out again. I kept trying, and did meet someone I liked through the same site. About 6 months later, my new guy took me to meet a friend of his in Toronto. We met her and her husband... the same man I'd had a date with 7 months earlier. They had been married for about seven years, so they were definitely together when we met. I didn't say anything about it, but he was obviously extremely nervous. He made his excuses, and left very quickly. His wife got a call a few minutes later: he had hit the back of a parked car on his bicycle, and had a broken hand and other injuries. His wife didn't have a car, so my new boyfriend and I had to take him to emergency. Very weird, and very awkward.
  • Oops iPAd sent before finished :). Online first date continued! It was a 12 hour first date and I knew he was the one when he kissed me good nite. One kiss at my front door and we set up our next date. I had a lot of "first dates" via online dating but I knew this guy was the one for me when one date quickly progressed to the next. So happy to be married to him for lots more awesome dates!!
  • First date was coffee but to me officialn
  • First date was coffee and a week later official first date golfing and brazilian steakhouse dinner on a Sunday (12 hours). When you meet the one, you know it!!
  • She was the girl of my dreams. We grew up together in the rural south, enjoying long, hot summers, climbing trees and sneaking cookies.
  • Lacan 1:15, is chillingly similar to my experience, 5 years, she moved to UK for 2 years to do a Master's, also trapped in UK for 1 week or so, but escaped to spain, bumped into a friend there Travelled around with her, but the rest was different....I met my new wife a few years later online (12 hour first date kinda thing, knew she was the one!).
  • So I meet a man while attending a family event. My family does not know him, but knows his associates and feels OK about me setting up a date for the following Friday. I am excited and set up a babysitter, get a pedicure and new outfit. On the day of the date, I text him to confirm our meeting. No response. At 4pm I call and leave a message. He calls back at 8:30 to say he is too tired and can't make it. He wants to reschedule and I politely decline making it clear that he missed his chance. Must not be meant to be, I tell myself and consider the matter finished.
  • I don't think I can top Cha-Diva for Worst Date, but in my books this was bad. First date, he took me to a hockey game (I hate hockey!). Second date to Canadian Tire. There wasn't a third date.
  • @you So I consider the matter finished and go about my life. The following Friday night I get a text at 3am. It is a picture of his junk! My family laughed and I posted on line for all the world to see. Really dodged a bullet there! Who does that?
  • Met her online a few years ago, we arranged to meet in a bistro on Bloor St one night. Everything going well, she excuses herself and disappears to the Ladies. 10 minutes go by. 15, 20. She eventually reemerges and excuses herself, saying she's in the midst of a panic attack and has to go home immediately. "I woke up this morning and FELT it coming on, should have stayed home." I ask her if she
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