This question originally appeared on Quora.
Answer by Karen Opas, editor and writer:
I’d say it would have to be the one where I put my date in hospital.
I was working as a waitress in a restaurant that saw a lot of upscale business lunches, back in the three martini era. The CEO of one multinational used to come through every few months and spend a couple of days taking people to lunch at the restaurant. He was friendly (and pretty drunk by the end of these four-hour-plus lunches), and he’d often ask me out on a date. Quite charmingly, which made up for the fact that he was some 40 years older than me.
After about two years, I said yes to a date. I figured it would be a fun dinner and then I’d disappear, dubious virtue intact. We had a lavish dinner in the rooftop ballroom of the Hotel Vancouver. We enjoyed cocktails, champagne, lobsters, a couple of bottles of red wine and then several rounds of double armagnacs. There was a big band orchestra playing and, despite the fact that I didn’t know a thing about ballroom dancing, he got me out on the dance floor several times. I was having a great time and so was he.
During the last dance, I decided to try and do the swoop with him in my arms. Did I mention that he was 6-foot-4? Over a foot taller than me. I dipped him down, and then I dropped him. And then I fell on top of him. I broke his collar bone. We spent the rest of the evening sobering up in the emergency room at VGH. He kept coming back to the restaurant, but he never did ask me out again.
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Answer by Tricia Hosein:
I was on an online dating site for about five months. I’d gone on several dates, and some didn’t go past phone calls. The one thing I learned from online dating is everyone has a story, everyone!!! Some are deal-breakers and some are just strange. Here’s one of my strange stories and the worst yet.
His blue eyes, blond hair, and athletic body profile picture caught my attention. We chatted through the site briefly before exchanging phone numbers. His deep, strong voice matched his 6’3 body as seen in his pictures perfectly. We talked and texted everyday for about a week and even exchanged a couple of pictures (normal head shots of us at work).
Phone conversations:
I learned that he was a huge Florida Gators fan. He talked about them constantly; he said he had many gator figures just randomly placed around his house and could tell if they’ve been moved or touched. (red flag No. 1)
I told him I wasn’t much of a college football fan, but if I were cheering for any team, it would be the Georgia Bulldogs of course (many of my friends attended UGA). He told me that they sucked and told me I WAS NOW a Gators fan. (red flag No. 2)
Our first and last date:
We met up at a bowling alley that was in between both our houses. I was there first and noticed him right away as he walked in. He walked up to me, picked me up, swung me around, and kissed me on my lips. Thoughts in my head: Umm what the hell is this guy doing??And, he better not kiss me again!
We sat and talked for a little bit, then he said he had a surprise for me. He pulled out a little bag from his back pocket and gave it to me. Inside the bag was a Gator shirt and matching panties!!!! Okay, the shirt I didn’t mind, but what’s the deal with the Gator panties??!! Seriously?!! Ummm this guy is getting more strange by the minute. (red flag No. 3)
As if that wasn’t awkward enough, he asked me if I could change into my panties and shirt in the bathroom and take a picture for him. Ummm NO, you freak!! I just looked at him like he was crazy and said, “You’re joking right?” He said, “Well if you don’t want to do it here, then you can come to my house, I only live 15 minutes up the street.” OK, clearly this guy is some type of crazy and I just want to go home, NOWWWW! (Deal-breaker)
I went to the bathroom and called my sister-in-law to tell her to call me in three minutes. (She’s reserved for situations like this.) When she called, I acted as though they needed me to come over to watch my niece because their babysitter cancelled last minute (my excuse every time).
I apologized to him and told him I couldn’t take his gift. He insisted I take it and made plans to see me the following weekend.
He texted me that night to ask if I had tried on the panties yet …
I blocked his number entirely after that.
Incidentally, the gator panties are my favorite at home panties for lounging. They are the most comfortable panties I have ever worn!
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Answer by Ridwa Mousa:
I don’t actually recall any bad dates apart from one occasion where I got “tricked into a date.” I was suppose to go to the movies with two guys I knew, and although one of them liked me, I figured that as long as the other one was there, it wouldn’t be too bad.
When I got there, it was only the one that liked me that was waiting. He told me the other one couldn’t make it; I could tell he was lying, but decided to make the most out of the situation. When we were buying our tickets, he pulled the whole I don’t have my wallet stunt on me. Again, I brushed this off and got our tickets.
As I always, always offer other people food when I’m getting some, I asked if he wanted some snacks. And boy did he want a lot. Looking back now, I don’t quite know why I just didn’t watch the film by myself!
During the film, he tried every known move to get a little something something; the yawn and arm over shoulder move, the attempting to touch my legs, and of course the “oh our hands just bumped into each other in the popcorn box …” I spend nearly two hours pushing his hand away and even avoided the popcorn box!
By the end of the film, I was annoyed, frustrated, and angry with myself for allowing him to ruin the film! He offered to walk me to my tram stop, and I reluctantly agreed. As we waited around and made awkward small talk, he suddenly got closer and tried to kiss me. I thankfully managed to dodge this by pushing him away and asking him what the hell he thought he was doing.
Best thing about the whole night? That the tram pulled up at that exact moment. I got on without looking back at him.
He continued to text and call me for a few weeks after that. Needless to say, he never got a response.
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