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Talk About Embarrassing Dating Stories!

Recently, in the spirit of Purim, I invited people to share their most embarrassing dating stories with me. We could all use a good laugh so here goes…

One time I was going on a blind date. I had arranged to meet the guy at a comfortable lobby in Manhattan and walk around the city. I had a close friend who lived nearby, so we got together that afternoon. She then accompanied me to the date a half-hour earlier so she could leave well before the date was supposed to start. We chatted lightheartedly, kidding around and laughing as good friends do, for about twenty minutes. Then she left the scene. I sat on a chair opposite the hotel entrance and fixed my eyes on the door, waiting and waiting for the guy to come through the door. I kept on waiting and he did not show up. After what seemed like an eternity, I began to look around the hotel lobby and noticed a guy sitting on a couch at the far end. We made eye contact and he stood up and walked towards me. Deep down I hoped that he had not been sitting there the whole time that I was speaking to my friend. Well, to my horror, the first words that came out of his mouth were, “Do you take your friends to all of your dates?” 

I was on a date with a guy at a restaurant. We had already been dating for a little while and I knew I liked him. I was not yet sure what he thought of me. I wanted to share more about myself with him. I had just come back from a trip to Israel and I wanted to show him an album with pictures of my family, so I brought the album to the date. I carefully opened the book on the table and then… knocked a COMPLETELY FULL GLASS of water all over him. He was soaked! Despite that, he was the perfect gentleman and told me it was not a big deal. I was mortified and sure that he would end it. Who would want to marry a klutz? Lucky for me, he still married me. We now have three beautiful boys together!

I volunteered for an organization for children battling a serious illness. I was asked to take a shift in the hospital taking care of a child. During that time, a handsome, tall, religious doctor with brilliant blue eyes came to visit our shared patient. I was determined to find out more about him. I roomed with other single women and one of them was in medical school. I went home excitedly and shared the information with that roommate to see if she could find out who he was. I described his features, the floor he had visited, and the time he came. My roommate called her colleagues and did her research. She confirmed that they knew who he was and that I should trust them. They were going to set me up with him. The evening of the date, I was all ready to meet this really handsome medical resident. The doorbell rang and I flew down the staircase from my second-floor apartment to greet my prince. I noticed his beautiful blue eyes right away. I also saw that he was short and balding. It was not him! We went out to eat and had an OK time. As he was walking me back to my apartment, he ventured to actually ask me if he was the right person. I was too embarrassed to tell him the truth, so I did all I could to give him the impression he was the person I had meant to meet. I thanked him profusely and somehow ended the date on a good note. He wanted to go out again, but it did not work out.

I had dated a girl several times over several weeks. During one of our dates, we were sitting in the car on a busy street in the center of a Jewish neighborhood. Suddenly, a guy about my age walked over to her side of the car, glared at her through the window, and stomped off down the block. It was hard to miss his “if looks could kill” expression and her deep red face. When she found the words to speak, she explained that the whole time she was dating me, she was actually dating that guy too. I think she is married now, but not to either of us. Unfortunately, we both broke up with her after that experience. 

I had agreed to go out with a guy and we had set a date and time for him to pick me up. I waited for him for almost forty-five minutes until I mustered the courage to call him to ask what happened. It turns out that he had gone to the wrong house and they told him no such person lived there. He went back home thinking I had stood him up and he was caught in a prank! He came back to pick me up a few minutes later. And no, we did not marry each other.

I was on my first date with a girl and we went to a hip sushi bar. I was focusing on making conversation and finished all the sushi I ordered. As I was talking, I wanted to keep eating, too. I noticed the last remaining chunk of avocado that fell out of a roll and remained on my plate. As I started munching it, I could not miss the fact that I was mistakenly chewing the huge clump of spicy wasabi that accompanied the sushi. I felt awkward telling my date about my mistake and spitting it out, so I tried to keep a straight face and swallow. I did a great job and she did not notice. But it seems the taste of the wasabi spilled over onto my opinion of the date, which did not work out.

On my first date with a guy, we went to a golf driving range. It was a beautiful day and we were having a lot of fun. I had never gone golf driving before and he was showing me how to hold the club and swing it. As I was trying out my new skill, I clumsily moved back and banged into the wall between us and the next stall. I knocked over a can of soda that was balanced on the wall straight into the space of a seasoned professional golf player. I was mortified as I watched the brown liquid pour into his sleek, huge leather bag of custom golf clubs. I apologized profusely to him. He was surprisingly gracious and told us not to worry about it. He was having a lot of fun watching me learn how to play golf!! I never forgot his calm and kind reaction. He saved me from a huge embarrassment. Fortunately, my date smiled and said nothing about my clumsiness. P.S. – I ended up marrying that guy. 

Embarrassing dating stories are more than great for a good laugh. What can we learn from embarrassing dating stories to improve our relationships? Here are some questions you can think about or discuss as you share these stories:

  1. What character traits can you identify about the people in each story?
  2. What factors might have contributed to some of the stories ending in the people marrying each other and some not?
  3. What are takeaway points you can learn from each story?

We’d love to gain from your insights! Share your ideas in the comments below.

Wishing you much success,