We asked a few people to share some funny dating stories from their past. The group below is the first set of entries. If you have any funny dating stories to share you can put them in the comment section (or, if it is a long one, email it to us). We will do a new post when we get some more stories.

We were about to arrive at the first social event of the new season after settling into our ‘Single’s House’ in East Hampton. Arlene and I were High School buddies who reconnected to share a weekend room for the summer. I was recently divorced and she had never married. In our conversation during the ride out to the Hamptons, I told her that I was a bit anxious. Her reassuring response was that as a divorced woman my chances of meeting someone were statistically better than hers.

The classiest meeting place in town was packed that Friday evening with attractive 40 to 60 year olds on the first summer weekend. Nurturing my mixed drink an attractive man approached me and we began to chat. I was quite impressed with him as he was smart, charming and happily had asked for my phone number. Returning to my room that evening I enthusiastically told Arlene that I met a very interesting guy.

Heading out to East Hampton the next weekend Arlene asked if Glenn had called. Disappointed, I told her I didn’t hear from him. The following two weekends while driving out to East Hampton she asked the same question. Fortunately she stopped asking.

On the final week of the summer we went to our usual Friday night singles bar. After about half an hour, to my surprise Glenn walked over to me, “Do you come here often?” he said. “Yes, usually on Friday nights” I answered with a smile. Lo and behold he launched into his the same ‘patter’ word for word as had the first night of the summer, never remembering we had met. After listening politely for about 15 minutes, I excused myself and walked into the ladies room and laughed out loud! It was clear that Glenn was not my kind of guy…

Submitted by Aileen

One would imagine that no matter how crazy a man is, he would at least recognize the need to act normal in the outside world when going on a date…And on top of that one may assume he would pretend to be normal in front of me – a shrink.

He had a crazy need to impress me with delusional activities and creative endeavors.

My first clue was the number of professions he was supposedly accomplished in – pharmacy, carpentry, law and medicine. But that was only my first clue. I was still flattered by the attention and scintillating conversation and, of course, good looks. My second clue which still left me questioning and unsure, was his excitement about being elected the first American Ambassador to Israel.

Included in this was a flattering invitation to spend a week-end in Florida and escort him to the inaugural ball. He even invited my best friend, Ethel. However, the truth finally dawned on me, when he asked, “Do you know that I’m also a song writer?” I said, “No, well,” and I was about to get off the phone and he said, “Let me play what I just wrote for you. Give me a minute.”

So there I was, skeptical but still half believing him and, of course, very flattered (another word is stupid). All of a sudden I heard the distinct sound of a cd player go on, a full band, piano and clarinet accompaniment. The sound of Whitney Houston began to come at me over the phone. I continued to hear the record playing and he came back on the phone and said, “Do you like the song I wrote for you?” I almost choked, but managed: “Excuse me. I’m getting married in ten minutes.” Click.

Submitted by Ava

While I was in college a friend of mine and I both liked two sisters in our college group. I wanted to date the older one, and my friend wanted to date the younger one.

We decided to call them to go to a movie, but we never said who was asking whom.

When we picked them up for the movie, the older sister said that they had decided one of them would ride with me in front on the way to the movie, and the other would ride with me on the way home.

The next week we decided we better be more direct. So, I called the older sister and asked if they wanted to double date again. But I started by saying, “this time, I will be taking you and my friend will be taking your sister.” With a sign of relief, she agreed.

Submitted by Rick

I spent 3.5 years as a single mom. During that time I dated just two men – one of whom I married (who I continue to adore). Not long after my divorce, a friend invited me to attend a showing of The Phantom of the Opera. It was to be a girls-night-out. One of the women brought her guy pal along. He sat next to me and began to act as though we were on a date. He told me about the Opera and everything that was happening, moment by moment.

I guess he assumed I was too dumb to grasp the concepts on my own.

After the show, he walked me to my van. He said, “I’ve never dated a soccer mom before.” I glared at him and asked, “Who said you were going to?”

He went on to tell me that he was the Regional Manager of a popular chain of restaurants (this turned out to be true). He wanted to fly me for lunch on his jet. I declined. He made it clear that he had money and could buy me gifts and take me out for fancy meals. He called me for weeks, asking me to go out with him. He mentioned marriage at one point. Our future flashed through my mind: the restaurants he was in charge of had full length mirrors on every wall, in the bathrooms. I had asked him who designed the restrooms and he proudly told me that HE did.

I said, “So you want to look at yourself from even angle, even while using the loo?”

Yeah. No thanks. This is what Narcissism looks like. Literally.

Submitted by Mandy


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