A Few of the Best Dates I've Ever Been On

These are a few of the best/most memorable dates I've been on. Not in an particular order, but just how I remember them.

The Kiwi

I went on a date with a Kiwi. A Kiwi is someone from New Zealand. I learned that amongst other things that night. It was our first date, and our only date. I met him downtown and had no idea what he had planned for the evening. We ended up taking a ferry trip around lower Manhattan to see the waterfall art installation that was up and then out to a New Zealand restaurant. I wrote in detail about this night in a blog called “Waterfalls and Kiwi’s”. I learned all about a bunch of things from him that I didn’t’ know about and we had a great time. There really wasn’t any initial attraction and we didn’t go out again, but I still had a great time. It was awesome to have someone put so much thought into a first date and really try to show me himself. I’ve dated people for months that told me less about them then I learned about him that night.

Anne Rice and Thai Food

It was Feb of a few years ago when I had my first date with someone that was a surprise. He was deeper then I thought he would be. We went to a Thai restaurant in Hell’s Kitchen and talked about books the entire time. Our favorite authors, places we had visited and places we wanted to go to. I love talking about books and its rare that you find someone in NY that actually reads a lot. I think his favorite author may have been Anne Rice, which I’ve never been able to get into. I picked up one of her books after that date, The Witching Hour, and I’ve never been able to get past the first ten pages. After dinner I walked him to some bar tending gig he had and we didn’t kiss. Generally if I really like someone, I won’t kiss on the first date. Is that weird? It’s like I’d rather hold off and just wait. When we did eventually kiss, it was worth the wait. I remember I was so nervous for our first date, on the subway I was listening to “Tonight, Tonight” by the Smashing Pumpkins, if my memory stands, I listened to that song before every date I had with him. I’m not sure why, but I know that every time I hear it, I think of him.

Madonna

I had been seeing Madonna for a while. Not the “real” Madonna, but rather someone that calls himself Madonna all the time. It’s always semi irritated me, but it kind of makes me like him more now. We had a “date night” and we would take turns picking out restaurants and planning the night. On this particular night we went to the Waverly Inn and had an amazing meal. The mac and cheese there is a hundred dollars a plate and well worth it. We sat in the back garden room and he moved his chair to the side of the table, next to the fireplace, so he could sit next to me. We drank wine and eat our faces off. It was ridiculously romantic and I felt special. It was awesome to have someone be so attentive and beautiful. On our way out we saw Meg Ryan eating and of course, the paparazzi outside didn’t give a fuck who we were, but one flash would have been nice. ☺ We then had drinks at a random bar that I’d never been to and then went back to his place. He has always been one of the best cuddlers I’ve ever had. The timing was wrong in our lives, but we actually had a ton of great dates and I’m sure one day he will make someone very happy. He will always have a special place in my heart.

Celebrating 20 Years of Sadness

I had been seeing this guy for a few weeks, and I had gotten us front row tickets to see The Smashing Pumpkins. He arrived late from work and we rushed up to the theater. It was way up on something like 170th street. It was a beautiful concert hall that I believe had once been a church. The architecture was beautiful. We started drinking beer and he whipped out his camera and insisted on taking tons of pictures. We got to our sets and stood the entire time. We danced, drank, kissed, held hands, and had an amazing time. I remember at one point, he simply leaned over and kissed my forehead, such a simple gesture and yet so wonderful. He was a horrible dancer, and it just made me like him more. After the concert we hopped in a cab where we cuddled the entire way downtown to a diner. We stuffed our faces, drank cheap champagne and talked about everything. He had to work in the morning, so he hopped in a cab and headed home after that. A little while after he sent me a text to tell me how he had such a great time and how awesome I am. On the way home I was listening to this song called “The Boy” by the Smashing Pumpkins, “I can't stop, I can't breathe, I can't think, I'm in love again
I don't need, I don't eat, I don't sleep, I'm in love again.” That night I told a few of my friends, “I’m absolutely falling in love with him.” We never saw each other again.

The Best of The Worst

This date is exactly the opposite of a great date, I think that’s why it sticks out and is one of the best I’ve ever had. It makes for a good story. This would be the first date of the second time this guy and I had started seeing each other. It had been probably a year since we had stopped seeing each other. Word from the wise, if it didn’t work the first time, it won’t the second. And generally, you will be reminded of exactly why it didn’t work the first time pretty fucking quickly. We met at his place, and then walked to what is one of my favorite restaurants in NY. Also, I recommend using the same restaurant with different dates. Is it just bad karma or setting yourself up for the same disappointment? I’m not sure, but I’ve stopped taking people to the same places. Honestly, this is NY, there are restaurants everywhere, so there really is no excuse. The first thing he said when he opened the door is, “wow, you are wearing a lot of colors..” in which I responded, “great to see you too.” Being the loud obnoxious guy he is, I brushed it off, and besides, he is pretty hot. I sat down on the couch while he finished getting ready, before we left he came over, wrapped his arms around me waist and kissed me. Then as he released he laughed and said, “How big is your waist, like 24?” At this point, I should have gotten up and walked out, but I didn’t. I kind of smirked, pushed him off me and said lets go to the restaurant. On the way to the restaurant, I was telling him how I had seen Christina Ricci recently and almost choked. She is one of my favorite actors and I didn’t say anything to her because I was too nervous. His response was something along the lines of, “Really? Christina Ricci and Alanis Morissette, we need to find you some new people to look up to.” We ate dinner and eventually after we went back to his place and had sex. Of course we still had sex, he was hot. And I think I like the battles a little bit. I didn’t call him the next day, or the next week. Eventually he sent me a text asking how I was and wanted me to go out with him again. I declined, and he couldn’t understand why. So I told him. He apologized, and I said I’d talk to him later. I never made the effort. Possibly one of the worst dates ever, and I still had sex with him? What was I thinking? I think I was thinking that even though he was an asshole, I still wanted him to want me. I was maybe 21 at the time and I had a void of a recent break up and he happened to fill the void for an evening. I think he will always be that kind of person, amazingly attractive, loud, and critical of everyone else. I’m sure he always gets what he wants, but I think inside he is probably just as sad as a lot of people and just as hurt, and also a lot better at covering it up.