I felt like putting together a post compiled of bad dates. And so people I know and people I don’t know eagerly sent me their bad date experiences to include. I’m happy to report that they are awkward; they are rude; they are weird; they are downright awful. They are even – at times – hilarious.
Hope you enjoy these bad date stories as much as I did.
Rena*
A few years ago, I met a guy online. His photo was nice – we texted a 
few times and seemed to have similar interests. So after a few weeks, we arranged to meet up at a coffee shop. When I arrived, I saw him immediately – but I was confused – because it was April and he was dressed up in a costume. The image is forever burned into my memory – he was wearing velvet, royal blue knickers – as in pants to just below the knee – white knee-high socks, royal blue velvet loafers, a white blouse with ruffles down the front and a royal blue velvet waist-coat with tails. I kid you NOT! I had no idea what was going on. Meanwhile he was beaming at me. He eventually must have clued in on my confusion because he explained: he was dressed as Prince Charming. Yes – my prince charming. If the ground could have opened, I would have gladly jumped right in. But did I leave? No – I did not. I sat down and we proceeded to have an actually half-decent date. But after that, I was done. Just too weird for me.
Anita*
Blind date . . . He called me saying he had tickets to Grease at the Hummingbird Centre (in Toronto). Thought that was odd for a first date however decided to go. I invited him to dinner beforehand so I was equally paying for the date. Finish dinner and go to the venue a little early. Have drinks then proceed to our seats. Second row . . . centre . . . great seats. Feeling a little impressed. We are chatting away. Venue stars to fill up. Two people sit down next to me . . . he leans over and and says: “Hello. How are you?” I find 
this odd but figured he was a friendly guy. Within seconds a couple sits down next to him and he says hello again but this time adds: “Where’s everyone else?” My expression must have said it all before I blurted out: “How do you know these people?” Drum roll please. His entire FAMILY had bought the first two rows of seats!!!!!! Are you kidding me was all I could think. Within a minute the first two rows were filled with family waving and yelling over.
That’s when I realized: I was on a blind date with two rows of his family!
During the intermission they stood in a huge circle while I hid in the bathroom. At the end of the performance they were all going to a bar. Not me. I thanked my date and said goodbye to dozens of his family members. Never went on a blind date again.
I can laugh about it now . . .
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Trina*
Worst date: I was crushing on a guy who worked at a bar. We exchanged phone numbers, and he called me, inviting me to a concert event out of town. I had to work the day of the concert, he said he’d pick me up and drive. He picked me up, but brought me to his mom’s house where he begged her for the car. It turned out he was only 18. I was in my 20s with my own apartment. Awkward. Eventually she caved and he drove us the two hours to the concert. It was so late that we missed dinner and most of the event 
before the concert. They loaded us all up on busses to take us to the mystery concert. It was Lenny Kravitz at a small venue. Amazing. All the free beer you could drink. He realized four of his buddies were there too and suggested that we crash in their hotel room. So . . . me, first date guy and four of his dude friends in a hotel room. Surprisingly, I wasn’t into it and started looking for an alternative way back home. As it turned out, a local radio station had sponsored a bus for the event, and someone gave me their bus ticket to get me back home. Once back in my home city, a couple of guys who worked for the radio station brought me back to my apartment.
I had to work the next day. First date dude shows up at my work with flowers.
There was no second date.
Margot*
I met John at a work-related conference. He seemed nice – he was definitely handsome and I really liked how confident he was. Fast forward to our first date – he chose a fancy restaurant where he assured me he was a regular customer. He was so rude to our waitress that I was just in shock. He spoke to her in a nasty tone – as if he was better than her. He complained about every aspect of her service – she wasn’t attentive enough, she was too slow, his food was cold. I was mortified. I have no idea if he was just nervous or else a raging a**hole – my money is on the latter. But I never went out with him again.
Cora*
A friend set me up with a friend of a friend. I didn’t have much to go 
on in terms of background information or even what the guy looked like. My friend assured me that he was nice looking and a great catch – so I told her to pass along my info. He texted me soon after and we graduated to talking on the phone. He seemed personable and friendly – he had a nice voice. We met up a few weeks later at a restaurant for drinks – he was really cute – and just as nice in person. But the date went south when he casually mentioned that he had eight children. Yes. Eight children. With five different women. I was so disappointed as I just knew I would not be able to get past that. There was no way I had the energy to worry about five exes and eight step kids. So at the end of the date, we hugged and parted ways. I guess he could tell I was zoned out because he never even bothered calling or texting me again.
Olivia*
I met Bob on match.com. We set up plans to meet at a trendy martini bar that was central to both of us. I dressed up a bit because it was the first time we’d be meeting and also this bar was higher end than a regular pub. Bob showed up wearing K-way tear-away pants. I didn’t get the best first impression of him. I soon realized that Bob was a real story-teller – and by story-teller I mean bullsh***er. He basically talked non-stop – and to be perfectly honest, I didn’t interrupt him or interject because his tales 
were so far-fetched I wanted to see what would come out of his mouth next. He told me all about his ex-fiancee who he caught cheating on him with the handyman they had hired to build the arch for their upcoming backyard wedding. According to Bob, he was suspicious and followed her only to discover that she had driven to the handyman’s house. He then looked in the bedroom window and saw the two of them in bed together. I didn’t even ask him how he managed to peek into a bedroom window that was most likely on the second floor – I chalked it up to the fact that he was Spider Man (in K-way pants!) He then told me that he drove home, packed up his ex-fiancee’s clothes and drove back to dump them on the handyman’s front porch.
As much as I realized that there was no future for me and Bob, my friends convinced me to give him one more chance. For our second date, we met for lunch – and I have to admit – he was dressed nicely this time around. But all throughout our meal, he talked non-stop. He bragged about the enormous cottage he apparently owned as well as the fact that he had a housekeeper at both his house and cottage. Then the conversation turned to previous dates he had gone on with women he had met online. He told me that he was on a first date with one such woman – they were at a bar – and when the bartender told her he didn’t have her wine of choice in stock – she suggested they go back to her place. When they arrived, she went into her bedroom and left him alone in the living room. After a few minutes, she called out to him to come into the bedroom and when he did she was completely naked and spread eagle on the bed. He told me that he was so taken aback by her forward behaviour that he turned around and hightailed it out of there. Then he went into the story of another woman he had met online – they had gone out on several dates when she invited him over to her place for dinner. When he arrived and knocked on the door, she opened it wearing nothing except for an apron. It was about at this point when I had enough of listening to this guy’s porno fantasies. We finished lunch and I left – I never saw him again.
Lorna*
How I met my partner, well – husband – well common law partner to be clear:
The first time I met Dan was at a bar. Sitting on neighbouring bar stools.
I had been raving about eating lunch at what turned out to be the restaurant where he worked as head chef. I bought him a shot and said: “Thanks. Your food is awesome.”
He told me to go f*** myself and drank the shot.
Turns out he was just ending a serious relationship and had a rule that he didn’t talk to anyone after work until he had finished his first drink.
We didn’t speak again for three years – I thought he was a total a**hole.
Next time we spoke was at the same spot. Same bar. Sitting on bar stools. Same bartender even. He told me my boyfriend treated me like sh** and bought me a shot.
He was right. We became friends, started dating and were pregos with our son a year and a half later.
And still together . . . probably because we can tell each other off once in a while.
The end.
Ned*
I usually keep things strictly professional at work, but I really clicked with this one customer, so I did I did something I’ve never done before – and asked her for her number right then and there. We talked throughout the following week and set up a first date at a local restaurant. I offered to meet her there, to take the pressure off of her having me pick her up and drop her off.
One of my personal rules is to to avoid too much chat before the first date, to leave ourselves something to talk about in case things get dry. Well, I violated this rule in the days leading up to the date, and we continued to chat on the phone.
My first inkling that things were probably not going to go well was during one phone call, when she said to me – “Don’t take this the wrong way but . . .” – never a good sign. She proceeded to tell me that I used the phrase “You know what I mean?” an awful lot. I know I do – but didn’t necessarily appreciate this being pointed out to me by a woman I had known for a total of one week!
Since the kid gloves were off, I decided to notify her that she also had an annoying habit. I think it was that her voice jumped to a high pitch at certain words in a sentence, but honestly, I can’t remember.
Anyway – we met at the restaurant as planned. Dinner was okay, but after only a few minutes she started talking about marriage and kids. Obviously her biological clock was ticking – but maybe a first date with someone she barely knew wasn’t the right place and time for that conversation?
After dinner, she wanted to show me her office so we got in her car and she drove us there — leaving my car back at the restaurant. Her office was nice — as nice as any restaurant, I guess. While there, I suddenly got really nervous. I felt trapped – in every sense of the word. She started talking marriage again. I told her I wanted to head out, but she kept changing the subject. She would show me another room, another door, another chair — anything to keep me there. I must have started to sweat profusely or show signs of a stroke, because she finally agreed to drive me back to the restaurant parking lot.
So, we get back, and I’m about to get out of her car when she starts up another conversation. Every time I hinted that I was tired, or it was late, or just wanted to wrap it up, she would change the subject and talk about something else. Finally, I had enough.
I don’t know what came over me, but as she was in mid-sentence, I elbowed my door open, dove out (yes . . . DOVE), raced to my car, got in, started it up and screeched away without looking back. I figured that was that.
Except a couple of days later she called me. “I don’t know if I should be offended or not“, she said. “Offended? Why? No, no . . . I was just tired.”
As this new conversation dragged on, I searched my house for another door to dive out of . . . but none appeared.
-excerpt from my memoir: The Gentle Art of Making Enemies.
Larissa*
On my first date with Dean (whom I had met online) – we met up at a restaurant for a drink. I know this wasn’t his fault – but it was still very annoying – he had the whiniest voice known to man. And it didn’t help that he seemed to be a miserable human being. All he did was complain about his life – he kept going on and on about his former job – which he had gotten laid off from. Anyway – when the bill came, he generously offered to pay which I accepted. Then he looked at the bill and when he saw how much my glass of wine cost – he pushed the bill back into the middle of the table and said: “On second thought – how about we split?” Of course I have to mention that my glass of wine cost a grand total of $8! I thought that was extremely tacky. I never did get together with him again.
Carmen*
I went for dinner at a steak restaurant with some friends when I was 21 or so. The manager gave me his number and said he’d like to take 
me out. A little odd I thought since we hadn’t even talked, but ok! He took me to Niagara Falls, which was also kind of odd when we hadn’t even ever had coffee or talked before. All throughout dinner he talked about his pending big move to buy a llama farm in Niagara and right there, asked if I would be interested in getting married and raising llamas. Uh nope.
After dinner, we split the cheque 50/50 and he calculated my share to the penny – even though he had lobster and I had something considerably cheaper – even though he was employed and 10 years older than me and I was a student.
Later, he unsuccessfully tried to kiss me by the falls, and asked if I wouldn’t reconsider the idea of marriage and a life of llamas. It was a long ride home for the both of us.
Tamara*
Though I don’t have any terrible date stories to share, I did go around with a boy back in Grade 3. We never spoke, walked by each other in the school hallways without making eye contact and he gave me a Christmas present via another person. I do recall going to the roller rink and he was there as well. We skated the moonlight and I was so nervous that I picked at my thumb as we circled round and round until it was bloody and raw. I was so absorbed in nervousness I didn’t notice the wound until I left the moonlit rink and stepped outside into daylight .
Bianca*
A guy I was really interested in invited me to his company’s work party on a dinner cruise. I went all out getting ready for the party (hair and makeup at a nice salon.)
During a romantic moment, he told me that I was the most naturally beautiful girl he had ever seen. Since sarcasm is my primary talent I jokingly replied “If this were natural beauty it wouldn’t have cost me $200 in hair and makeup.“
When we said goodbye, he tried to give me $300 in cash.
I don’t know if I was 1) more offended that he thought I needed a reimbursement or 2) more confused about the apparent $100 accrued interest.
Debbie*
Here’s one about the worst human I went on a date with
I met this guy at the gym. He was a personal trainer and I scammed as many free training sessions from him as possible before he asked me out. Have you ever dated a personal trainer? Or any man with a six-pack? They don’t eat real food. They have cabinets full of protein powder, tuna, and frozen chicken. That’s usually it. Anyway, he asked me to go on a walk though China Town. Totally normal thing to do for anyone who is NOT racist. I couldn’t believe the things he was saying out loud. Why would he want to go there if he disliked Chinese people so much?!?!? That was the last day I ever spoke to him. It made going to the gym pretty awkward.
Sadie*
He was a Portuguese guy – so let’s call him Gil (which means young goat in Portuguese).
When I met Gil, he was 32 years old and living at home with his mom and little brother. His father had passed and he was taking care of them. Admirable, right?
On our third date, we went to a chain restaurant where I ordered a simple chicken dish. He immediately commented (condescendingly) that my choice was boring, that I could make that at home and should order something different. I stuck with my choice even as he proudly ordered a fancy and more expensive dish that he could barely pronounce.
As we waited for our food, he sipped on a Caesar. I had just bought my first condo and he questioned me about how a good Italian Catholic girl was 1. Allowed to leave home and 2. Able to afford a condo (which he insisted daddy must have bought for me (Geez – not like I worked hard for many years and saved the money to buy a home!)
When our dishes arrived, he looked at his tiny pile of food with great sadness and disgust. I offered him a taste of my food which he quickly accepted without hesitation. He then decided he wasn’t going to eat his meal. I jokingly asked “Do you want to trade?” Without even responding, he switched our plates and guzzled down the food (I had déjà vu of the first time I used a garbage compactor). By this time, I lost my appetite and his nasty dish remained on the table untouched.
When it was time for the bill, Gil raised his hand to catch the waitress’s attention. From the corner of my eye I thought I saw a splash of red. He had somehow managed to spill his Caesar on his white shirt – under his armpit!
When the bill came, we both agreed to pay for our own meals. Rather than pay for his expensive fancy food that remained untouched, he paid for the boring dish I initially ordered and didn’t eat. So I was left to pay for his dumbass choice!
Needless to say, I made a point of never seeing him again after that night. AND I later discovered that the little brother he was caring for at home with his mom was 28 years old! Yep, admirable . . . No sarcasm there!
Avril*
I met Anthony on a dating website and we agreed to meet each other at a local coffee shop. When I walked in and saw him, I realized that the photo he had posted on his profile was about 15 years old – minimum! In his profile photo he had a full head of hair and was beefier looking – but here he was in real life – completely bald and skeletal looking – basically a shell of his former self. I just found it a dishonest start to a date but I got over it. We ended up going on a second date – but it was then that I realized there was no future for us. He had lived on his own for far too long and was very set in his ways and I could tell there was no flexibility or give in his personality whatsoever.
Meghan*
I met Mark at the grocery store. He asked me how best to cook 
asparagus and we got to talking. He was really nice and friendly and I will also admit – very good looking. There was a coffee shop in the grocery store and he asked if he could buy me a coffee after we bought our respective groceries. I thought that was pretty gutsy and sweet. Our coffee date was really nice. We exchanged numbers and about a week later, he texted me and asked me to dinner. It was a Friday night and we met up at a casual chain restaurant. Mark was already there when I arrived. We ordered some drinks and an appetizer – then Mark excused himself to go to the bathroom. There was a table with two small kids colouring and eating near the bathrooms and I noticed he spoke to them as he passed. I didn’t think anything of this – at first. But throughout our date, he excused himself several times to use the facilities, and each time stopped to talk to the kids. When I asked him about it – he explained they were his kids. It was his weekend with them and he couldn’t find a sitter. I was pretty surprised by this. Not that he had kids – he had told me this already. But that he basically brought them on our date and stashed them at a table by themselves. After our date ended and I left, the more I thought about the entire situation, the more upset I became. I just thought it was a pretty awful thing to do to your kids – he was supposed to be spending quality time with them. I’m sure his ex-wife would have been pissed to know he had brought them to a restaurant while he was on a date. Anyway, it just didn’t sit well with me – which is why I never went out with him again.
Joelle*
This was by and far the worst date I’d ever been on – maybe the worst date anyone in the world has ever been on. I met Michael online – and we agreed to meet up for coffee. He was cute and nice and the conversation really flowed. Unfortunately, that wasn’t the only thing flowing. I unexpectedly got my period and when I went to the bathroom, I saw that I had bled through my pants. But I was having a really good time and didn’t want to inexplicably cut the date short – I also didn’t want to tell my date about my dilemma. So I just put my jacket on and hoped that he didn’t notice. He asked if I was hungry (I was) so we moved our date farther down the street to a restaurant he suggested. Just after we ordered, there was a commotion in the kitchen – a fire – and the restaurant filled up with smoke. They announced that they were closing and all customers had to leave. We didn’t have to pay for our drinks – but we were still hungry – so then we went to another place nearby. When the bill came, Michael realized he didn’t have his wallet. He figured he had left it at either the restaurant before or else the coffee place. I paid and we decided to back track to find the wallet. On the way, I tripped over a piece of uneven pavement and broke my foot. The best part of the story though? We got engaged about 18 months later – and have been married for 7 years.
*Names have been changed