Cancel Culture

As I have mentioned in previous stories, I really didn’t date much during the pandemic, it was far too risky. However, I would text guys and just hoped to meet once vaccinated.

I was chatting with a guy from Tinder. He was in his 50’s, lives in the burbs and was a consultant. We talked a couple of times on the phone, but, mostly texted. He seemed nice enough, but his texts were so boring. He would just continue to tell me to have a great Tuesday, Wednesday, or whatever day it happened to be.

He also sent notes on Holidays. (or, Hallmark Holidays). I did get a Happy Valentine’s Day and a Hoppy Easter (yes, Hoppy).

Generally speaking, if a guy can’t put more effort into a text than "Have a Great Tuesday", I am probably not going to be interested. Admittedly, I could have put more effort into my replies, but I just wasn’t feeling inspired.

Shockingly, this went on for about 6 months. Part of that time I wasn’t even living in Chicago, but he would check in every couple of days.

After we both were vaccinated, I asked him if we were ever going to meet in person? He said he would love to.

Here is where I made my first error. He asked for a couple of options and regrettably, I gave Friday night as one of the choices. My general rule is to never accept a first date on a Friday night or Saturday night. More often than not, I will have major FOMO if my friends are out and about having fun and I am on a first date.

Sure enough, of all dates I gave him, he chose the Friday night. And, as luck would have it, I was invited to the Cubs game that Friday afternoon. Just like I suspected.

I could have gone to the game and the date, but I thought that wouldn’t be a good first impression for him. I knew I would have a couple of drinks at the game and be annoyed I have to leave early.

So, I passed on the game and our date was scheduled for 7pm. He was coming into the city.

At 5pm that night (yes, 5pm), he cancelled. He said he was in the emergency room with his sister, and he would need to reschedule. Here is the exact message:

I have to postpone our date tonight. I’m sorry, I’m hoping you will have some time in the future. I’m at the hospital with my sister. She had an accident. I’m not sure how long I will be here. Call you tonight or tomorrow. Sorry again. Look forward to meeting you.

Here is the million-dollar question. Is this BS? Or, legit? I don’t know him well enough to have any idea. I asked opinions of friends and it was a 50/50 split. Some said his message reeks of a lie and others said he was a good family man taking care of his sister.

What to do? Well, as you will probably know by now, I decided I needed to see this thing through.

So, we rescheduled on a boring Monday night where the only thing I was missing out on was watching the Bachelor. And, of course, that was DVR’d. Perhaps I will hand out my own rose on my date? Well, let’s not get ahead of ourselves.

We meet at a local bar and he is on time. (lucky for him – ha). He apologized again for cancelling on the first date. I didn’t even tell him I passed on a Cubs game, I just listened to his explanation. Apparently, his sister had too many drinks and fell down. It seems she does this quite a bit, so he seemed frustrated with this repeat scenario. Rightfully so.

He talked about his kids quite a bit. I am fine with that but there was something that surprised me. He was telling me about his 3 kids in their 20’s and how they use all of his frequent flyer miles, hotel points, etc. etc. but they don’t make much time for him. I said, I know when I was in my 20’s, all I wanted to do was hang with my friends. I get it.

He then said something about his 10-year marriage that just ended. I said, wait a minute, your kids are in their 20’s and you were most recently married for 10 years? He said, yes. I said, did you have the kids in a previous relationship? He said, no, they are my ex-wife’s kids. Ohhhhh so, they are his step-kids. It is starting to make sense why they are pressed for time. They have their Dad, Mom and Stepdad to spend time with. In my head I thought, “stay in your lane” but I just nodded and listened.

He then went on to say he has bought houses for 3 different women. I said, why? He said he was engaged twice before and just gave them the house. And he also gave his latest wife the house too.

From the way he was describing things, it seemed people take advantage of him quite a bit, which is typically not a good fit for me. However, he assured me he was just a good guy doing the right thing.

We had a nice time. He asked if we could go out again, I said yes. Guess what? He never asked me out again. He would just tell me to have a nice day in a text.

I was on the fence about him to begin with, and, he exhausted me to the point where I lost all interest.

Lesson Learned? I need to stick to my personal policy of no first dates on a Friday or Saturday night. And, dating fatigue is real.