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Dating and The City

Unforgettable Dating in NYC

Unforgettable | Dating & The City Episode 6

Tomo (Living in NYC)I am a single Japanese woman living in NYC. After ending the long-distance relationship with my former Japanese boyfriend, I went back to the dating scene for the first time in almost 10 years. Then I decided to try something that I had never done before– online dating with non-Japanese men. It was a completely different experience for me to date men from different racial and cultural backgrounds. They are typically good at complimenting ladies, carrying good conversations, keeping ladies entertained overall, and making them laugh by being funny. At the same time, it can be tough. What I say and do or what he says or does could be confusing, misleading, or even become a deal breaker. In my column, I will share my cross-cultural dating experiences from a Japanese woman’s perspective, hoping that they should be helpful as tips for those who’re seeking cross-cultural relationships (with a Japanese woman in particular).


Dating & City Episode
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Dating & The City Episode 6


I think everybody has one memorable or unforgettable date or two. I do. In this episode, I will share a story of my best date ever and give you some dating ideas to make your dating experience more fun and successful.


When I first moved to NYC for work, I started dating this man that I met at an Irish bar in the East Village. That day, I was going to meet up with my friend who was visiting NYC for a summer internship. I got there early, and the friend had not arrived yet. There were only a few customers at the bar because it was still early. So I sat at the counter, ordered a glass of beer and started watching a baseball game on a large TV screen as there was nothing else to do. I was sipping my beer and enjoying complimentary popcorn in a small basket on the counter. Then I noticed a guy who was sitting one stool away from me was kind of checking me out. But I ignored him and continued focusing on the game although he kept staring at me trying to get my attention. I said to myself, “He’s definitely interested in me!” Finally, the guy made a move. “Excuse me,” he said. I turned around with a shiny smile and replied “Yes?” Then he said, “Actually, that’s my popcorn.” I almost fell off the chair and said “Oh my god!! I am so sorry!! I will pay for this,” reaching out for my purse. He started laughing and that’s how we began talking. He was kind of cute and we exchanged numbers and ended up being in a relationship for about 8 months. Let’s call this guy ‘Jay.’


The Most Memorable Date Ever….
Growing up in New York, Jay knew where to go and what to do around the city and he was the one who officially introduced me to what this great city had to offer. He was such a wonderful ‘dater.’
The most memorable date of all was a picnic in Central Park. Jay took me to the Great Lawn. When we found the right spot under a tree, he opened a blanket on the grass and took out a bottle of white wine and two nice-looking plastic glasses from his backpack. He also brought some simple hors d’oeuvre that he had made. I was very impressed. You know, women love surprises, even a small one like this. I believe it was in late June and we had such a relaxing afternoon in the park. Everything seemed perfect—nice weather, breeze, great wine and food, and a cute and caring man next to me! I needed nothing else. It was just so romantic, and I thought it was very sweet that he had put together this simple yet chic outing for us. That was definitely one of the most unforgettable and romantic dates ever.


Playing Pool
Jay was very good at playing pool and for our third date, he took me to a pool bar in the East Village that he would frequent with his college friends. He taught me how to position the stick by holding my hand, explained the game rules and purpose of the blue chalk (before, I had no idea what that was for). Instantly, I got hooked on playing pool. When you play a game or do some physical activity together, natural physical contact with your date helps to bring a couple closer together as both of you are more relaxed and not too self-conscious. It can be bowling, table tennis, badminton, dance, etc. Playing cards or board games could be fun as well but those are more intellectual. Anything that involves physical activity should get your mind off yourself and help both of you to naturally loosen up more. I strongly suggest you try that especially in the case of cross-cultural dating with a non-native English speaker. It does not involve much verbal communication and it is simply fun. You might see a different facet of your date’s personality and understand the person better.


Museum Night
I loved art and Jay took me to Metropolitan Museum one Saturday evening because they were open until 9pm. It was much less crowded, and we could take our time to explore various exhibitions in a quieter environment. Love has always been one of the most common themes and subjects of art throughout history, and we could find many men and women, lovers, or couples like us in old paintings. Some looked serious and dramatic, some were humorous, some were sensual. We could easily relate to them and project ourselves onto them. I also felt like we were traveling in some foreign countries far away. The idea is to get lost in time and space, being immersed in the old art works that are telling the stories of people from all walks of life in the past. That experience will put your life in perspective. After the museum, we went to a very small but chic wine bar on the Upper East Side and talked about which paintings we liked and exchanged views and observations about each others’ favorite pieces over a glass of wine. That was quite enjoyable.


Simply, Taking a Walk in the Park
Jay and I would often take a walk in the park. Simply strolling around the park hand in hand as we chitchatted was relaxing and kind of nice. Although we didn’t really argue about anything most of the time while I was with him, when we had some issues such as him getting too busy with work and not being available sometimes, we would talk about it and sort it out. Walking in the park gave us a good environment to do that because the natural surroundings calmed us down and made us feel more grounded.


Shopping at Macy’s
It was the week before Christmas, and we were at Macy’s because Jay needed to do the final round of gift shopping for his family (he was Filipino American and his family was so big!). Then, when we met up at a busy intersection of the Macy’s ground floor lobby, he showed up with a big stuffed animal. It was ‘Curious George’—he remembered that I loved the character, and he had seen me carrying several of the character goods such as keychains, tote bag, and mascot. “So cute!!” I exclaimed and squeezed George. For the rest of the day, I held George in my arms as if holding a toddler. Passersby smiled at us, and I felt like I was in a Hollywood romcom movie or something.


As you can see, Jay was an excellent dater and knew how to please me, but he didn’t necessarily have to break a buck to impress me. A date does not have to be extraordinary or extravagant. You don’t have to spend a lot of money or take your date out for a nice dinner at a fancy restaurant to ‘wow’ her. As I said, women really appreciate when men show small kindnesses or gestures of caring, like buying some flowers, asking if she’s comfortable, or remembering what she likes. Jay was very sophisticated in doing all that.
It’s more than a decade ago, but to this day I remember Jay and the many fun dates that we had together. Those are the old days when I started out in NYC and I wonder what has become of him since.


(Written by Tomo)


I am looking forward to her Dating & The City – Episode 7!

Naoko Matsumoto
Founder & CEO of Traditional Japanese Matchmaker


Naoko Matsumoto Traditional Japanese Matchmaker

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