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Dating: A Woman’s Perspective

Fairfield County women dish on their most memorable dates.

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 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 Match.com. 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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