Crazy Time Date

I know the focus right now is on the election mayhem and I considered writing a blog about my thoughts on that. I’ve chosen to pass, as I just don’t think another opinionated voice is needed at this juncture.

Instead, I will distract with the continuation of my renewal of my dating life. I believe I left off with with my mini dachshund Charles humping the head of the person I was with on New Years Eve.

Again, I took a break of several months before moving forward. Having so little experience in dating I also was very inexperienced in understanding women’s “signals” when they were interested in you.

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 I was also still working. Across the street from my apartment was a restaurant, that when I first moved in, was Austrian cuisine. Shortly after I moved in, 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 from out of state and I let her stay at my place to save money. 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.

So my friend suggested she would talk to her and explain the situation gently. When she got back to the table she had her phone number for me and told me she would go out on a date with me. Well, that was bit unorthodox but OK, at least I got my answer without my ego getting crushed.

Now here’s where it gets crazy for a couple of weeks.

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 this park on the westside with a 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 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.

Well that didn’t happen and the night got even stranger……. to be continued.

Sunshine Always! Stay safe.