A Grown Ass Man - Part 3

I say to him, no I absolutely do not want to split the tab for dinner. He said, OK, you can get the next time. I said sounds good, I will get the next time. (wink wink).

Now remember, I had already agreed to going for a nightcap with this guy. I was completely annoyed but carried on with the plan. We get to the next bar and have a drink. He was talking about future plans together and I just smiled. I could have won an academy award for my performance.

Now, the bill comes for the drinks. The server places it in front of my date. I say to him, I will get this one. He said, great and didn't even put up a fight! The server looked at me and rolled his eyes. I was like, get me out of here!

He offers to drive me home. Now Chicago is not the safest these days and I still said no, I would rather walk. So, if that gives you any indication of my annoyance.

By the time I got home, he had texted me and said what a great time he had and wants to do it again. I said, thanks for dinner and avoided his request for future plans.

The following week, I happened to be going out to dinner with my friend who knew him from high school. She was on the edge of her seat waiting for an update. I told her the story. Shockingly, she was kind of on his side.

She said, you know, he has been out of the dating game for a while. It probably was first date jitters. I said, did your husband call you a Grandma and ask you to split the bill on your first date? She said no but, this guy is a great guy. You should give him a second chance. She said maybe he thinks women want to pay for dinner these days.

Well, not this woman. The first 3 dates should be on him if he does the asking. Then it can even out a bit.

I feel if he was rusty with dating, he could have said, you know, I have been out of the game for awhile but would love to treat you to dinner if that is OK with you? Or something to that effect. I mean, do I have to think of everything?

She said just tell him you will meet only for a drink. So, against my better judgement, I text him and say we can meet for a drink.

He said, let’s go to Three Dots and a Dash in the city. This is a place with great drinks and gives you the feeling like you are on vacation. It is very tropical. He then starts texting me all of these Hawaiian songs. He is excited because it is reminding him of his place in Maui. Please, don’t remind me of that place in Hawaii!

A couple of days later, my friend who vouched for him texted me and said, you know, I have been thinking about it. I don’t like it anymore. I said, now you tell me! I already committed to a drink.

I said, tell me again the last time you spoke to him? She said oh, high school. WAIT WHAT? I am going on your recommendation, and you haven’t talked to him in 30+ years? Why I aughta….

I was dreading this date. Dreading it! Like, I would rather stare at a wall. So, a couple of days later, I am out with one of my friends who is single. I tell her the story. She said don’t you dare spend any more time with this guy. Wouldn’t you rather be home? I said yes, would so much rather be home watching Real Housewives of Anything but the date is tomorrow.

Secretly, my biggest fear was that I was going to "school" him on the date. For instance, if he started talking about future plans, I would say something like “oh, I assumed we were just friends when you asked to split the bill”. It just wouldn’t have ended well.

My single friend said you have to get out of the date and be very direct. Otherwise, he will still think there is a chance. We crafted this message. Here was our exchange:

Sue: I have been thinking about tomorrow. I am not feeling up to it because I don’t think we have a connection and don’t want to waste your time. I wish you the best.

Date: No problem, Sue. Thanks for letting me know. Our mutual friend will be very disappointed. Can I still call you for favors for hotel rooms? Good luck with your search.

Sue: I am sure another hotel chain has you covered for favors. Good luck to you too.

I am relieved I got out of the date. Our mutual high school friend texted me the day after the date asking how it went? I said oh, I changed my mind and cancelled. She asked how did I get out of it and I shared the screen shots.

She said, ouch, very mean. The irony is, I thought this was the nice way out!

Then I remembered he called me Grandma and didn’t think it was mean at all.

Lesson Learned? I am all for second chances. However, if what happened was so damaging, you may never recover from it and should probably move on. Bow out as gracefully as possible! And, always protect your time. Don't waste a second of it!