Dating: A Woman’s Perspective

Fairfield County women dish on their most memorable dates.

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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



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