Dating Again Mid-Life Style

As I have settled into a new life over the last several years, with a new wife, new job, new home and most recently, new title(Grandpa), an interesting memory came back to me. I like to call it "the crazy date."

After my wife’s passing I was spending more time in a small apartment I had rented in the city. Until then, I basically just used the place during the time she was ill to go back and forth to the hospital each day, while still working in the city. Across the street from my apartment was a restaurant. When I first moved in, was Austrian cuisine. Shortly after, it became a Greek restaurant, owned by a very popular Greek chef.

The convenience of the location had me going there with friends and many nights just by myself and sitting and eating at the bar. The owners and workers of the restaurant were very welcoming and made me feel like this was a little home away from home that I could go to as an escape.

The owner and chef had quite the loyal following. From Tony Bennett to Ryan Seacrest to many other New York heavy hitters. On any given night you never know who you would run into in the restaurant.

As time went on, I couldn’t help noticing this rather attractive brunette, who was the hostess most nights. She always wore black, which in retrospect should have set off some bells and whistles in my head. Again, I’m a 50+ year old dating rookie at this point.

I was going there on occasion with this other friend, who would come to NYC for work. We were talking one night and I brought up the hostess and said I wonder if someone like that would even be interested in me. My friend asked “well are you interested in her”. I gave a vague response out of my own insecurities. I did go on to say I felt like she was flirting with me more and more upon my restaurant visits. Of course, I also felt she might be flirting with everyone in the restaurant.

My friend suggested we go and she would observe. Fairly quickly, I got the “Oh she is definitely into you” response. That sent both a wave of fear and excitement through me. But now what? Do I just ask her out? Do I give her my number? Get her’s? I am terrible at this, I must embarrassingly admit.

I contacted her and we text and decided to set up a Sunday afternoon brunch at a place she frequents near her apartment on the upper East side. So far so good. We sat and had brunch in a cozy booth and we talked, or should I say she talked……and talked….and talked….and talked. I discovered she was divorced and had a young son. She seemed a bit adventurous, but I discovered she was an international model for a few years at a very young age.

She was Brazilian and Italian. Oh….yes….I almost forgot. She told me she thought she was an alien. A what? An ALIEN!!!!!!! Like from another planet, not country. Again Chris, an alarm of some kind should be going off in my head.

The reality was that I was not looking for or expecting some deep relationship out of this. I was for the first time in my life planning on just dating some different people. She was certainly different. So I figured I would give it a go again and I would plan the date.

She had said she liked to try different things on dates, unique places and or experiences. She suggested I meet her at the restaurant where she works, which was a bit odd considering it was her day off. For me, that made my life easier as I lived right across the street.

We were meeting at 3PM. I had planned to take a car ride up to Fort Tryon Park on the westside with a beautiful scenic overlook and gardens. They have a little cafe and bar there, so I figured we could have a drink, soak up some of the late summer beauty in the park and get to know each other a bit more. After that, I made reservations for us back in midtown at a steakhouse that featured a live Jazz trio on a stage while you dined. Thought it would be different and a bit classy. I thought…..

This is going to be a long strange story, so get ready. I may not put in all the details at this point, but I think I can still paint the picture for you, if you’re still following.

So I meet her at the restaurant and we start chatting it up with the owner and staff over a glass of wine. I tell her we should get going to the park so we have time to enjoy it before we have to head back downtown for dinner. Apparently her hearing wasn’t so good. Or maybe it was just that she needed to show that she was in control. An hour went by with more wine flowing and I gave up on the park idea as she seemed indifferent to the plan.

Then after about 90 minutes at the restaurant, she suggests we go around the corner to this hotel rooftop bar for a drink before we head to dinner. Personally, that’s fine with me. Less running back and forth in the city during rush hour means less stress. Plus I’m feeling pretty relaxed from the wine on an empty stomach already.

We get to the rooftop bar, which I will say had a spectacular view of the city and Central Park. However, the bar was quite crowded with all the tables and couches taken. As we were standing and looking around, a couple of middle age guys from Israel started small talk conversation with us. At first, I thought maybe they were interested in my date, but as the conversation went on, it seemed less the case.

We drifted over to the bar to order a drink and separated from the guys. While waiting for the bartender to get our drinks, my date just blurts out to this guy standing on the other side of the bar, “you have the most beautiful blue eyes”! First off, I kind of thought it a bit awkward on a date with a guy you would compliment the eyes of another man. Secondly, well he kind of did have amazing blue eyes.

So while she strikes up a conversation with him, I get the drinks and work my way toward them. He turned out to be a really nice guy visiting from Boston with his husband. Husband?….OK…see Cimino, no threat.

In the meantime, our two Israeli friends, see me from across the room and wave us over. They have snagged a table and want us to join them. I ask her to come with me to go and hang with them for a bit. Much like my futile attempts to get her to leave the restaurant earlier to go to the park, she ignores me.

So I decided to walk over by myself. Actually it was a good thing. The three of us quickly fell into conversation about what my story was, what she was all about and what was our relationship. These guys generously bought a couple of bottles of champagne for the table and some food to snack. To be honest, at this point, I was feeling no pain, but needed some food in my stomach to sponge up some of the alcohol.

My date was still chatting away with the gay guy with the beautiful blue eyes. I decided to walk across the room to try and get her to join us. Again, I pretty much got the wave to go away. Now, I won’t lie…..I’m getting pissed off and want to end the date. I went back to join my new friends at the table. When I got there, the one guy, who was fairly recently divorced, said to me “you see what you just did”? “Don’t do that. If she’s really into you she’ll get her butt over here, don’t go chasing her, that’s what she wants.” At this point I’m thinking to myself, I don’t want to play games. If this is the dating scene, then I’m out. I just wanted to go home and end the date.

So I continued to hang with my new friends. We actually got into some deep conversation, as of course we had plenty of time to do so. As I was talking about what the last few years of my life were like, the conversation led to being able to contact those that have passed on. They told me they have this amazing psychic in Time Square that they see every time they are in town. They wanted me to see her to maybe give me some connection and peace in my life to the losses I had experienced. At this point I was half way sold on the idea, but I have to say these two guys also had my BS detector going off.

As I went to go find my so called date again, they were going to go to their rooms before heading to the psychic. At that point I was intercepted by this very enthusiastic fan of the show. She was celebrating a birthday on the rooftop bar and she wanted to take some pictures. Of course I agreed, and that was followed by my FaceTiming her mom who was in a nursing home, but apparently even a bigger fan. It was really a sweet moment in the middle of what was a very strange uncomfortable date.

Of course in the midst of this, someone suddenly made her way across the room as she noticed I was getting attention. It was getting close to the time we should be leaving for our dinner reservation at the Jazz restaurant. Of course I was still debating bailing out and going with the guys to the psychic, but I still wanted to be a gentleman.....at this point.

So we regrouped at the table, the guys had already left. I told her they were expecting me to meet them in the lobby in a few minutes. She waved her hand dismissively, "we're not doing that"!

So again, I stupidly acquiesced . As we were heading out of the hotel the doorman said hello to my date and then she started a rather animated conversation about something that had happened when she was there a few nights earlier. I came over to introduce myself (she wasn't going to do it) and I said hello and shook his hand. With that, she gave another dismissive wave to me, as if I was bothering her conversation.

Well now, I'm done. Game over! Date over! Night over!

We started walking down the block to get a taxi, which in my mind is now going to be where I place her to go home by herself. As we are walking toward 6th Avenue I told her I don't think this is going to work. She asked me what was wrong. Wrong? Where do I begin.

As I started this new chapter of my life I promised myself I would be more honest about my feelings. I would speak up if something was bothering me instead of just accepting and swallowing it. So I let her have it. I told her she was rude to me and dismissive. I was not going to accept that and I would prefer we just go our separate ways. As the words came out, it felt good to speak my mind and my feelings so honestly for a change.

Of course I did not get the reaction I was hoping for. She began to cry and make excuses. I don't do well with a crying anyone, or tearful anything for that matter, in terms of me staying strong. I fold like a cheap tent. She convinced me to continue with the date. Mistake number.... I lost count already.

We get in the cab and get to the restaurant and are seated facing center stage, perfect view of the live jazz trio. The level of the music is ideal to appreciate, yet still hold a pleasant conversation. The level of the table on the other hand was not so perfect. It wobbled slightly if you leaned on it a certain way. A slight bother, but not a big deal once you realized the type of leaning that caused it. Well, not a big deal to me, but there was someone else at the table remember.

She kept complaining about it. She would say it was unacceptable and she would never allow this in the restaurant she worked. I kept suggesting we ask for another table, but she would tell me to forget about it and then bring it up again two minutes later. Why didn't I escape when I had my chance on the rooftop bar?

So the appetizers had arrived and we ordered a cheese board with some charcuterie. She suggested in a playful way we each make a little mouthful combining the various meats, cheeses, crackers and dips on the plate and feed it to each other with the person being fed closing their eyes. OK....this could be fun in it's own delectable way.

I believe she fed me first and I said that it was an interesting combination and I enjoyed it. I fed her and of course it was met with a litany of negative comments of why it didn't work, what I should have used instead etc. At this point I'm hoping I choke on a cracker and get out of there.

Now it's time to order the main course and she decides to order the branzino for two. Odd choice because she told me she wanted steak, hence my choosing this place known for its steaks. In addition, the restaurant she works in, and I frequent, is well known for its branzino. In my opinion, the best in town consistently. I'm thinking, why would you order something you can get where you work, and know how good it is, at another restaurant.

Again, I let her have her way. As we are listening to the music and chatting, she is getting a little more flirtatious. So now, with a bit more wine in me, I'm hoping maybe it was just some early in the date jitters and apprehension I was experiencing. Insert buzzer sound....WRONG!!!!

The fish comes to the wobbly table and is fillet and plated in front of us with the accompanying sides. She takes one bite and throws the knife and fork down into the plate, actually startling the jazz trio on stage. She grabs her napkin and spits out the piece of fish into it while shoving my plate away from me and covering it with my napkin.

She starts yelling how "the fish is bad, don't eat it, you'll be sick". I tasted it. While it wasn't as good as the Greek restaurant she worked in, it was fine. This is then followed by her trying to get me to kiss her, in between her texting someone on the phone. At this point, I'm back to get me the hell out of here mode.

The texting continues while we ordered a dessert and an after dinner drink which was now on the house due to her complaining of the fish(which we were not charged for either). I finally asked her who she was texting and she said it was some guy from Spain who was in the U.S Tennis Open for a couple of weeks. The players stay at the hotel nearby the restaurant that she works and they met her there, I presumed a couple of times. She said they wanted her to come to a party at a hotel in Times Square. Perfect. Here's my out. I told her, "why don't you go?" I said I would walk her there safely and then I could be a free man. So I thought.

I got the check and paid as quickly as I could and we began walking toward Times Square and her tennis player "friends" from Spain party. I didn't say much on the walk as I didn't think there was anything that could be said. This date spoke for itself.

As we got to the corner where I was going to go my way and her to the party, she turned and looked at me and said she wanted to stay with me and then began kissing me. Excuse me, but WTF???!!! She's just so unstable. At this point, I've committed in my head to this being a joke and I'm just going to have fun with it, however it ends up.

So I asked her "what do you want to do?" She suggested we go back to the restaurant where she works. I'm not sure why someone on her one day off from work wants to spend so much time where she works.....but OK. It was a good 20 block walk to the restaurant, and no, that did not go uneventfully either.

As we are walking through the packed streets of midtown Manhattan, like in typical pre-Covid days, she randomly blurts out to me that she has " a magic vagina". Uhhhh.......ummmmmm.....ok then........... As if that wasn't enough, as we are waiting at a corner for the light to change, she asks two, probably tourist middle age women, if they have magical vaginas. I let it pass for a minute or two and then being in the science and news business I asked, " what makes it so magical?" Her head whipped around to face me and she said "how dare you ask me about my vagina?!!" I said, "well you were the one who brought it up....not me." If the cuckoo bell sound effect could have gone off, it was blaring in my head at this point.

The good news was that walking to the restaurant was also walking me closer to my apartment and my final escape. Once again.....so I thought.

We keep walking and her next topic in her words.... " balls!! What good are they? Why do men need them?" I have to be honest, at this point I'm looking for cameras. I'm not worthy of being punk'd, but boy do I feel like I'm being set up on some reality show.

My response to her was that she had a son and without them he wouldn't be here. Oddly her answer to that (or maybe not so odd) was, " well my husband only had one ball". OMG.....too much information. When is this going to end. The conversation went onto grooming down there, I will spare you the details. However, once again, going for the shock value, she asked two random strangers, young men on the street, if they shave down there. I'm not making this up. "True story", as Jay Leno would say.

So I'm going to wrap this up and probably leave out a few more details. The night didn't end there. We went back to the restaurant and had more wine which was followed by the owner of the restaurant taking us to another rooftop bar after she closed up. Another round of her flirting with other guys there, then playing a cat and mouse game with her boss of not letting it look like we are really on a date.

At this point I'm fried. I have been up since work, about 2:30AM and now it's 1 AM the next day. Quick ending is, I got her home, enduring a few more comments in which I did let her know at the end of the night were offensive and emasculating to me and I don't take that in silence anymore.

In summary, as crazy as this date was, it gave me a hint of what the dating world could be at this point in my life. Maybe I should just find a cave and call it a life.

Little did I know what was coming my way from the ashes of my past. What joy and rebirth and discovery was awaiting me in the heart and soul of someone I had already known for over a decade. You already know a lot of that story. I'm sure I will write in more detail about how we got to where we are today. Not that this relationship with Edmi didn't come with growing pains....but at least she doesn't blurt out to strangers about having any magical body parts.