We get to the restaurant and as we are being seated, he said, BTW, if you get into a fight with someone tonight, I won't slap them on your behalf. I said, huh? He said you know, like Will Smith. Oh, now I get it. I said, I know you don't know me very well but, I am a total delight. No chance of me getting into a fight. (truth)
We sit down and he starts ordering food and drinks. It happened to be Restaurant Week in Chicago so there was a pre-fixe menu (or, you could order off the regular menu). He said, let's order off the pre-fixe menu and get the 5 course meal.
Now, I am not someone who needs all of that food, but, I was trying to be agreeable so I said fine. And, then he said we need to order a pitcher of sangrias. That works too.
We start talking about alot of work things. It was fine but I am off the clock and would rather talk about anything more fun than work.
He then asked me how many times I have been engaged? I said - ZERO! He said WOW. Weird, no? I said, not for me but perhaps you being married for 20 years might find it odd. I told him I have so many friends who are in my same position as me in the city. He said, I just don't understand why you wouldn't have been married? I said, would it be better if I was divorced? Perhaps that would make you feel more comfortable. But, I am glad I am not.
We then moved off that topic and started talking about what we did the weekend prior. I told him my nephew had invited me to his college for a Ladies Day at his fraternity and it was so much fun. He said, when you were walking up to the house, did they say, here comes GRANDMA? I said, wait, WHAT? Are you talking to me? He said yes.
I assured him that my sister and I were the ones who got the party started and brought the sizzle to the event. I couldn't believe he said this to me and decided I am not going to defend it further. I was gobsmacked. I have more youth in my pinky finger than this guy has in his entire body. Bring back the work talk!
Shortly after he said that, I told him we would need to get a picture together. I knew I would need back up when telling this story. When people see the picture, they said, it looks like a Father Daughter picture (of course, these are my friends) but it was clear he was projecting his feelings on to me.
Perhaps he forgot how to woo a lady while he was married? Or, maybe he never had that skill?
So, now we are done eating and drinking and he asked if we could go to another bar afterwards for a nightcap. I was super hesitant but I agreed because I thought we couldn't end on this note. Side note, being an optimist can be exhausting.
So, the bill comes. As I have mentioned in previous stories, the boss move is for the guy to slide it next to him so it is understood he is paying it. After all, he invited me and planned the night.
The bill is just sitting on the table like a hot potato. The server comes over and asks if she can take it. I say no, there is nothing in it yet. He doesn't react. Just lets it sit there.
The server comes over again and asks if she can take it. I say, still nothing in it yet.
I am like what in the alligator arms is going on?
By the third time the server comes over, he said, oh sorry. We will take care of it soon. He looks at me and says, DO YOU WANT TO SPLIT THIS?
I say, DO I WANT TO SPLIT THIS, NO I absolutely do not want to split this!!
What happened next? Stay tuned for part 3 next week!
hLesson Learned? I am not going to teach a 50+ year old man how to act and help him hone his social skills. Also, I am still super chivalrous and like the guy to pay for the first couple of dates. And, if the big spender can't afford it, don't pick a fancy restaurant and order everything on the menu. I would have been fine with just one drink for our initial meeting.
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