My top shidduch dating fails

This post will be a whole lot better if you folks participate. I only say this because although I have several funny fails from my short lived shidduch dating career, I am sure that you all have your own stories to share – so enlighten us. I’m not sure why I haven’t utilized the #fail or #epicfail as posts about random frum things, but I may as well start somewhere. What better place to begin than with one of the most talked about items of the frum community.

I was on a date several years ago with a gal quite a bit older than I. It was my first time dating someone in her 30’s and I’m not sure we were on a level playing field. We were walking through Central Park and I had mentioned something about how I give fist bumps to people who were hacking and coughing the entire shul so that I shouldn’t have to shake their hands. She responded excitedly and said “oh I remember the first time a guy fisted me” I kid you not, Hashem somehow gave me the strength to keep a perfectly straight face as she continued to say all of her “fisting” stories.

I asked out this fairly frum girl at a party once and we were on our second date at a comedy club and the comedian decided to do some of the dirtiest material I have ever witnessed. Once again I tried not to laugh as I saw her putting her mental earmuffs on.

I like to repeat this often, but I once was on a date and needed to pee desperately. So I did what any logical tree hugger would do. I tried to find a tree, my date was very offended.

I was on another date in Central Park and it was maybe 20 below zero, we were bundled up and already the girl was proving to be quite weird (remember that I am super weird myself which translates into clinically insane for normal people) She decides that amidst this freezing weather we should have a spitting contest. Then at exactly 1.5 hours she ended the date saying that she always had 1.5 hour first dates.

I was out with a girl in Passaic and we went to some Israeli join on the main drag there. I ordered a steak or something easy to eat and she ordered a shawarma in a pita. After the first 3 bites, the bottom of the pita fell out and got all over the place.

I was once out in Monsey with a girl and I was having a good time, but the place we were at was closing and I was super hungry. I wanted to go to this pricey place for dinner, but was too poor to pay for my date so I asked if we could go Dutch and she readily agreed. Later that night, the shadchan called me in a rage, telling me that Dutch was unacceptable.She also called later that week to tell me that writing about how my date was a bit over weight was uncalled for – that was the last time I wrote about a date that soon after.

I was coming back from a hiking date with a girl and she told me she was gonna be sick. I pulled over and watched in horror as she puked her brains out on the side of the road. I wondered if she was all talk and if she had drunk anything all day or during our 12 mile hike. I also felt really bad.

I was once sitting at a Chinese Restaurant with a girl who flew in to date me, when she asked something about how I thought it was going, I got this sour and obvious look on my face. She asked me to be honest and tell her if it was her looks, so I was honest and learned that there are just some things you can never be honest with girls about.

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