I’m putting the challenge out to the blogosphere and wider community to give me your “shortest” date stories. And before you start tapping away on your keyboard with stories of the 4 foot wonder that showed up one day, stop. I’m not talking about your vertically challenged friends. I’m talking about those dates that you didn’t deem worthy enough to last longer than an episode of Gossip Girl. Was it 30 minutes; 20 minutes or even 5 minutes?
They can be your stories or those of a friend’s, or even one of those urban legend dating stories. Tell us how long they lasted; why; who ended it and how; was the ending truthful or was it an excuse? I’ll start the ball rolling…
My friend, Leanne lived in New York. As she was a recent transplant to the city and didn’t know many people, she signed up for online dating. She’d been on the site for a while by now, but was becoming quite disillusioned with the quality of guys available therein.
She had heard and seen of this phenomenon in New York City called “multi-dating” where people would date multiple people at once (no not actually on the same date!). These multi-daters would have multiple dating relationships going on in parallel, for any number of weeks, or even months. In fact, on her first night in the city she went to a party where she met one guy who had two dates scheduled on the one night! Apparently not such a rare occurrence in the city. Eew.
Anyway, if this was the norm, and she was now a resident in the city, she was willing to give it a go. When in Rome, and all. And a lot of dating advice literature came out in support of this method – that way you aren’t putting all your eggs in one basket and pinning all your hopes on the one person (and other clichés like that). There was one problem. She couldn’t find enough guys she was interested in (and vice versa) at any one time to be in the multi-dating mode! Quite a dilemma.
She thought that if she was going to try out this dating method, she would probably have to lower her standards a little, and maybe be a little more proactive. OK. So here’s what happened. She noticed that this kinda cute guy had looked at her profile, so she decided to get in contact. For the purposes of anonymity we’ll call him kindacuteguyNYC.

So Leanne and kindacuteguyNYC had one or two message exchanges through the dating site. So far so good. And then it came. What came? You ask. Well, if you’re single in NYC and you meet a seemingly cute/normal/nice guy there’s always a little voice in the back of your head waiting for the other shoe to drop – “Why is he still single?”. Sure, many people ask that.
But in a city where, according to Richard Florida, the author of Who’s Your City?, single women outnumber single men in NYC by 210,000 (numbers are from 2008). That’s a HUGE imbalance.
So, it came. The answer. The warning bells were going off after this one. Leanne received an email from kindacuteguyNYC saying:
“I don’t mean to be so forward and I probably shouldn’t ask this but I would rather not waste either of our time, and I’ve been caught out with this situation before. I noticed that in your profile pictures you only had headshots and I also noticed you said your body type was “athletic”. Could I just ask you what your bra cup size is? I really need it to be at least a “B” cup.”
(Note to Match, JDate, eHarmony etc – add “bra size” as an attribute!)
Leanne was taken aback. She knew New Yorkers were pretty up front and direct, but this was taking things to a new level! Besides herself, only Victoria’s Secret knew her bra size! So, dear readers, what do you think she did? If you guessed, “Never responded to him again”, you would be….smart, and ultimately smarter than Leanne was.
“Maybe this was the way men in the city behaved?”, she thought. ”And were his physical requirements for women so wrong, after all?” She considered that she also had certain physical requirements for the men she dated, so was it so wrong that guys should have them too? She took the logical, sexual equality based approach to this and continued the conversation.
“You’re right, you shouldn’t have asked it, but for the record, my bra size is [insert a cup size of B or larger here]“.
This seemed to satisfy him. His response came back very apologetic and he politely requested that she give him another chance and that they meet for a drink, where he would make it up to her. She wasn’t quite sure why she agreed to meet with him after this abysmal start, but he had promised to make it up to her. So they made plans to meet up on Sunday evening at 8pm.
As it turned out, the bar they had planned to meet at on Sunday night was shut, so after they had completed the greetings pleasantries, they decided to walk up the street to a bar/restaurant. The walk half a block between the closed bar and the open bar seemed very long, very awkward. Where was the guy that promised to make it up to her? Things seemed quite uncomfortable between them.
They sat down in the bar area of the restaurant and the waitress promptly handed them the drinks menu. And then she asked them if they wanted to see the food menu. Now Leanne had absolutely no expectation that they would be eating a meal together. But she had been on dates when they had gotten something small to snack on. So she asked, “What do you think?” to her date in regards to looking at the food menu. He responded that he couldn’t eat as he had to head back to work soon.
So, if you had just met someone 7 minutes ago and they were already talking about having to go somewhere else, and that somewhere else was work, on a Sunday night, what would you think? Well, Leanne thought the same thing. He’s obviously not so into her. Leanne’s time was precious to her and she didn’t see the need to play out a scenario that was already looking doomed, so she said, “Well do you want to just end the date now then?”.
KindacuteguyNYC seemed quite shocked at her up-frontness and he said “No, why, do you?” She promptly said “No”. But then she thought about it. And she realized this date wasn’t about to improve from here, and this guy was just as much a douche now as he had been in asking her for her bra size. Can you imagine if girls asked guys their size before agreeing to go on a date? So, she said, “Actually, yes I do.” And she walked out. 8:08pm.
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