Dating: A Woman’s Perspective

Fairfield County women dish on their most memorable dates.

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


The Therapist

I’m fairly new to the area and so I signed up with an online dating website as a means of meeting people. I received a lovely email from someone who was separated but not yet divorced. I responded despite my being leery of doing so. Although this gentleman had moved out of the family home and was living on his own, I got the impression that he was not really ready to be dating. He seemed intent on meeting me, however, and suggested that we go for a long walk at Tod’s – keep it casual, informal he suggested. It was a beautiful spring day, early in April, and I was up for a nice beach stroll. We met by the concession stand started chatting and walking, what ensued would be an hour’s worth of free therapy given to him by me. It wasn’t exactly the date I had in mind but this guy was so appreciative of my advice and my attention and, truth be told, it was nice to be able to help someone in a time of need. We never had a second “date,” but now many months later we are very good friends!
—Amy, Old Greenwich

A Jerry Seinfeld Episode

You want to hear about a date? Something funny? Maybe crazy? Nothing too serious? Can I tell you about more than one? Sometimes when I go on dates I feel like I’m on an episode of Jerry Seinfeld. You know all those quirky people they talk about? If they’re out there, I’ve dated them. I once had a date with this man who, during the meal at a very upscale restaurant, pulled out a nail file and started to pick his finger nails! I’m not sure which was worse, that or the man who picked at his teeth throughout the meal. I had a coffee date with a man who asked me out but didn’t pay for my coffee, a date with a man who did nothing but talk about himself; I tried but I couldn’t get a word in edgewise. I’ve dated men who did nothing but talk about previous girlfriends, about how perfect their children were, even men who barely spoke a word. The last two were tough! I had a date with someone who insisted on bringing his dog, because his dog was a very good judge of character, and someone who brought his kid! His kid!
—Danielle, Stamford

Across the Sound

I received an email from someone on who lived on Long Island. When you specify a dating range, the website calculates miles but doesn’t distinguish between the towns that are on this side of the Long Island sound or the other side. It was such a nice email that I thought I should respond and I did. I told him if not for the body of water that separated us, he would be my ideal match. An email returned to me moments later. What’s a mere thing like a body of water? There’s always the ferry – a quick and lovely ride. I hadn’t thought of it that way and while it made sense, I really hoped to meet someone a bit more local. But he was persistent - very persistent! He convinced me that we really should meet up. He insisted on hopping on the ferry, getting a hotel room and taking me out to dinner. And so, before I knew it I was driving over to the Artisan Restaurant in Delamar Hotel in Southport where he had booked a room. We had a wonderful night and I bid him farewell long after midnight. We met up the following morning over bacon and eggs at the Driftwood Diner while I nursed a headache from the good wine we’d had the night before. The following weekend I took the ferry over and spent a lovely couple of days at The Three Village Inn in Stony Brook while we wandered the coast across the sound and dined at the lovely and romantic Mirabelle Tavern. Soon he would travel to Europe for work and it would be a few weeks before I would see him again…in Europe! I had a business meeting of my own and by sheer coincidence our schedules synced and we continued our dating experiences in London. It was like a fairy tale. The handsome Brit and me…dining at lovely restaurants, walking through the Covent Garden at night, and strolling the streets of London and wandering into the latest trendy pub. All this with the man from across the sound that I almost turned down!

Alas, we are no longer dating. In the end our busy careers and the commute proved to be more than we could handle but we had a couple of magical months and although brief, it was wonderful to be treated like a princess!
—Katherine, Westport


 The Longest First Date

We agreed to meet at a restaurant in Westport for a late lunch. I think we met at around 2pm. He took the seat by the window looking out in to the restaurant and I took the seat across from him, looking out the window. It was late in February and a cold day. The restaurant was warm and cozy. We started chatting immediately and the conversation was smooth and effortless. While we were talking he reached into his pocket and handed me a very small brown box and asked me to open it. It was a fragrance from Provence. He had just gotten back from a trip to France and we had, a few days earlier, been talking about the country and I reminisced about the years I had spent there during my childhood. The pretty bottle was a small gesture to remind me of the days and scents of my youth. I was incredibly touched. The afternoon passed by without warning. We’d finished our pizzas but the Barolo kept flowing as did the conversation. Neither one of us paid any attention to the time. Outside I could see the shadows shifting to a darker blue; the sun was starting to set. I remember thinking it must be late afternoon. Anything I needed to tend to could wait – I had nothing pressing on my schedule. Street lights were coming on and headlights passed us by, traveling from left to right. Inside the lights came on as we were still chatting. Around us tables had seen a revolving door of activity with people coming and going, movement all around us. But we stood still. For a short while there were no other diners in the restaurant, and then slowly they started trickling in through the front door. Overhead the lights dimmed to accommodate the dinner crowd. Outside, the sky was almost purple. Once we realized what had happened, how long we’d been seated and how long we’d been talking, seemingly without ever coming up for air, we started to laugh. My date asked the waitress if we could have a dinner menu. Upon checking the time it was now 7:30! I’m sorry, she replied. Your table has been reserved. Perhaps another table then, he asked. We were told that all tables were reserved. So at 7:30pm, roughly five hours after our date started, we walked out the restaurant, hand in hand. But neither one of us wanted the date to end. So we meandered across the street grabbed a couple of stools and cozied up to the bar for a couple of hours. Midnight was on the horizon and we both had to go and face the realities of the next day and all that had been put off. We walked to our cars in the parking lot; he gave me a sweet parting kiss. That night I drove home with a smile on my face. This date took place about two years ago and when I think about it, it still brings a smile to my face.
—Carolyn, New Canaan

Goin’ to Vegas!

I met this guy on I thought he was cute. He seemed nice in a boyish, charming kind of way. We talked on the phone a few times before deciding that we should meet out. The place, date and time were all selected. In the meantime this man was traveling fairly locally and we chatted some more over the phone while he was away. On his way back home to Connecticut, he called to tell me that he was looking forward to meeting me. Our conversation was fairly short and was followed by one other brief conversation. He called a second time to tell me that he had to fly out to Vegas for a family emergency. His elderly mother had fallen and broken her hip and he was going to try to grab a flight out that evening. Something about his story didn’t sit right with me. I’m not sure what it was or why, other than the fact that my instincts were trying to tell me something. His subsequent activity on Match told me so. His mother hadn’t fallen. She wasn’t in dire straits. (If she was, shame on him for not giving his own mother the attention she deserved!) Vegas? Really!!! That’s awfully far to go to get out of a date!
—Tamara, Riverside

Big Bold Italian

A friend set me up on a blind date. I don’t do blind dates. But this gentleman seemed just my type - academic, scholarly, intellectual, intelligent. As he described what he did (we spoke on the phone a couple of times prior to our meeting) I imagined tweed, cords, glasses, and loafers… maybe even a pipe or cigar. I imagined a character out of Love Story. A true New England preppy. I had a good feeling about this date! We met at the lobby of a hotel with a restaurant where we had planned on grabbing a drink at the bar. Have you ever been on a blind date and wanted to run out, quickly, before the other person saw you? I have. I experienced it that very moment. Only he saw me and I couldn't turn around and run. I wondered if I looked shocked or if my fake smile looked real. I don’t mean to criticize anyone’s dress style, but I thought I had stepped into a time warp back into the 1980s. My date, Gene, was wearing a black Members Only jacket, a burgundy paisley button down shirt, olive colored corduroys – Levis, and Wallaby shoes. The only reason I knew what the shoes were was because when I was in sixth grade they were all the rage along with our Bonne Bell Lipsmackers! This was just too funny. Hush Puppies? Members Only jacket? We couldn’t have been more mismatched with me in my black boots, black skirt and top, faux fur cropped McLaughlin jacket, and pearls. We must have looked a sight! Where was my true New England preppy? It went from bad to worse really fast. He asked me what I wanted to drink and I thought aloud to myself, wondering if they have a Super Tuscan. “Whoa!”, he asked, “What’s a Super Tuscan? Sounds like a big, bold eye-talian like myself!” He wasn’t quiet, in the least. I just about died and shrank three sizes. There was no Super Tuscan so I settled for a Chianti.

We simply had nothing in common to talk about. Nothing. He had prejudged me and I suppose I had prejudged him, and we were unable to find common ground. After he finished his gin and tonic, and pretty damned quickly, he said ‘I gotta go’ and off he went. Where did he go? To the rest room or did he really go, as in go? I sat there for a few minutes; my Chianti not quite finished, and wondered whether he’d even paid for our drinks. I did inquire on my way out, just to be sure. After about ten or so minutes I got up to leave, saw and chatted with a couple of friends then made my way to my car. As I walked out of the restaurant I looked to the right, in the direction of the restrooms, and there he was, almost smack dab in front of me! He looked like a deer caught in headlights. Had he been hiding and waiting for me to leave? I said something like “Oh there you are! I was waiting for you so that I could say goodbye and thank you for a wonderful time!” As he looked even more shocked, I headed down the stairs and out to my car.
—Francesca, Southport



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