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Dating: A Woman’s Perspective

Fairfield County women dish on their most memorable dates.

Photograph: © AmmentorpDK/istockphoto.com

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Dating at midlife can be a strange thing. Getting back out into the dating world is scary and intimidating, but it can be wonderful and even wildly funny. As we search for our Prince Charming, we’ll no doubt find a few frogs along the way; we may even kiss a few of them. Below some fellow Fairfield County ladies share some of their more humorous dating experiences.

The Ghost

I hadn’t been on many dates, since my divorce, and I was still trying to figure out what to do, what to expect, what the rules were. One of my earlier dates happened to be with a widower who was about my age with children roughly the same ages as my own. I was a little nervous about meeting him – I wondered whether he was still pining for his deceased wife; it would be hard to compete with that, you know? I calmed my nerves and met the widower at a lovely restaurant in Greenwich where we had a nice dinner. Conversation was effortless, but he did talk about his wife – a lot. He used words like “love of my life” and “soulmate” and I had pretty much ruled out any prospect of a second date at that point. I had no interest in competing with a ghost with whom he was still very much in love. He was a nice man – calm, gentle, easy to listen to and so I did not mind letting him talk. It seemed like he needed someone who would be willing to listen to him and let him tell his story. I was more than happy to be that person. After dinner, he walked me to my car and I thanked him for a lovely meal and proceeded to dig for the keys in my purse. At that point I looked up as he was leaning to kiss me goodnight, which I was not at all expecting, and suddenly he’s kissing me, full on kissing me… passionately. He had me in a stronghold. I couldn’t wriggle free. It was funny and bizarre at once. He never called me again.
—Cheryl, Greenwich


As a woman, I feel that I can never be too safe when I meet someone out, especially someone I don’t know, so whenever possible I try to get some background information on my date. Usually, I don’t find much out there – some business links, work related photos or a Facebook page. My hope is never to come across any police or criminal records. It’s never a good thing when you do. One man who tried to pursue me was allegedly arrested for breaking and entering into his ex wife’s house, even though it was still his home as well. Even though it could have been a misunderstanding or something harmless, I decided to stay away from him. Another gentleman, a good bit older, was trying to impress me and convince me to go out with him. His age was a great concern to me – we were at very different stages of our lives. In fact, he had grandchildren who were as old as my children. The likelihood of any sort of relationship was unlikely though I agreed to meet him out for a cup of coffee. Prior to doing so I decided to Google this very preppy, distinguished older gentleman. His name came up immediately and was all over the page. I was about to have coffee with a convicted felon who had done time in jail, not for anything remotely dangerous or violent, but still!
—Sara, Stamford

Blind Man’s Bluff

A couple of summers ago I was out with a few friends. It was a warm, early summer evening and we all were in good spirits as the weather seemed finally to be turning in our favor. A gentleman and I struck up a dialogue about a home that he was renovating, with my background in art and architecture the conversation flowed with ease and grace. As my friends and I were getting ready to leave, he handed me his business card. “Email me,” he said. I took the card, tossed it into my bag, and didn’t give it a second thought… for a day or two. There was something about that gentleman that was unique. I couldn’t put my finger on it but I was intrigued. But email? Really? Is that what’s done these days? Don’t people call anymore? I lingered over the whole email proposition for a while before deciding that I had nothing to lose – so I did. The very next day we talked on the phone and he revealed that he was blind. He used the term blind even though he was really more visually impaired. His eyesight was very blurry, he explained, and therefore he wasn’t allowed to drive. This new discovery really made no difference to me and so I agreed to meet him out.

It was a hot, humid, summer night and because of that I traded in my jeans for a sundress. The dress, you will see is an important part of the story. I was headed out to meet my visually impaired date. I worried about not being able to recognize him, but luckily, I found him seated at a table in the bar area. We each had a glass of wine before heading over to the restaurant area where we had a reservation. Over the course of conversation I decided that this guy wasn’t for me. We were quite different in very many ways. He didn’t like anything on the menu and when he finally ordered something, he returned it. As we continued talking he looked down and told me I had nice legs. I work out, I’m in decent shape, but I would never go so far as to say I have nice legs. I looked at him sort of incredulously, and with complete loss of control, (I think I may have actually shouted this) I said “Oh my God, you really are blind!” Yeah, he never asked me out for a second date!
—Samantha, Fairfield

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