Sangria’s, X’S and O’S

Over the last week, my Italian ‘fish’, Joey, has quickly slipped away back into the dating pond. I’m just as confused as many of you may be – after reading about the successful date I had with him two weeks ago. At any rate, I was back on the prowl and might have found myself an even better contender.

Meet David: a 24 year old accountant who also appreciates high tea and shares a love for traveling.

We had been talking back and forth on OKCupid for just over a week, when we decided to move things over to Facebook. The first thing I noticed was that our birthdays were three days apart. Thought that was pretty neat. Next, I saw we shared one mutual friend. Turns out that mutual friend was a girl I went to both elementary school and high school with! As I looked through a few pictures he was tagged in, I put the puzzle pieces together and figured out they were cousins. Small world! Anyway, I suggested the two of us go out for drinks to celebrate our birthdays.

Which leads us to tonight.

The two of us met up at Jack Astor’s Bar & Grill for drinks and dinner downtown. When I got there he was already waiting in the front entrance and stepped outside as he saw me walking up the stairs. He was very cute – just like in the pictures! We hugged each other hello and then proceeded to sit down at a booth inside the dining room.

We looked over the drink menu, and decided to share a pitcher of red Sangria. I could tell David was pretty nervous, as I was initiating the majority of conversation towards the beginning. Maybe it was just my beautiful presence which made his knees week. ;) Anyway, I felt like as we continued making our way through the bottle of Sangria, he felt more at ease and asked me more questions.

We talked about our families, and I was really pleased to hear how close he was with his parents and siblings. Our conversation pretty much covered all areas including places we traveled to, our University experiences, work life and pets (so happy he shared a love for cats like I do!)

The atmosphere was really nice and after about an hour of sitting down together, they dimmed the lights in the room. It was as if the waitress telepathically read my mind as it definitely made the setting more romantic.

Along with our Sangria’s, we shared a garlic bread and pizza. It was deelish! As we finished off our meal, I noticed there were some crayons at the table and our plates covered a sheet of drawing paper. That led into several games of X’s and O’s (which I won twice) and we also played a few games of hang man. Definitely a fun ice breaker activity on a first date. It was also a good way of learning what kind of bands he liked, cities he visited, and TV shows he watched. Even if you don’t have a Jack Astor’s in your city, I’m sure there is a similar restaurant that can allow you and your date to relive some of those classic childhood games.

Just over two hours later, he paid the bill (I offered to contribute) and we walked towards the subway. Once we got there I thanked David again for dinner. He said he had a nice time and hoped I got home safely. We had a nice hug goodbye and then we proceeded our separate ways. I had a silly grin on my face while taking the escalator down into the subway.

I texted him when I got home saying, “Hey. Just wanted to let you know I got home safe and thanks again for a great evening!”

David responded about ten minutes later saying, “Glad to hear that. :)”

I really hope he’s interested in going on a second date! Don’t want to get too excited, but I think he is definitely a good one. Thoughts?

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6 thoughts on “Sangria’s, X’S and O’S

      • Oh, I really don’t think you texted him too soon. We women get too hung up on whether or not we texted too soon or too late…we drive ourselves crazy trying to figure out what he meant when he said this…. auugh!

        You thanked him in a timely manner that you had fun. He responded in a timely manner. I don’t see why you couldn’t suggest another meeting. He could say no, but no guy would spend three hours with a woman he didn’t find interesting.

        And…men like it when a woman is CONFIDENT. Take a chance… you never know until you try…

  1. I love Jack Astor’s, never thought it would be a good place for a date though because of the noise!

    He sounds like fun, I would keep dating him and see where it goes.

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