I know it has been some time since I have shared actual dating experience on here. Full disclosure, I had mixed feelings about it for a while. I do enjoy telling stories, and sharing strange observations in this crazy world. Yet, both the sharing of experience from someone else and also with much more important things in the world, it seemed not appropriate to share.
Well, with the calendar turning, a new president about to be inaugurated, and too many stories to hold back, I’m saying F-It. Time to get some out there for people to enjoy and learn from. Here goes…..
COVID Dating Stories Part 1
Before we get to a couple of recent gems, I wanted to lay out my approach to dating during the strangest time in our lives.
- As I mentioned a while back, I got back on the apps in late May. Why? Well, to be honest, not going out much and being social, I do crave social contact. So, chatting on an app is a much better alternative to just sitting around.
- As always, I like a challenge. COVID has presented a very unique challenge to the dating matrix. If you have read previous posts, then you know that I like to plan unique dates that make for fun experiences regardless of the outcome. With the various limitations, my creative dating brain has gone on tilt trying to find fun stuff to do.
- To stick with the theme of the post – F-it!! I mean I know a lot of people are extremely cautious when it comes to COVID. I respect everyone’s choice to be safe and not to be social. However, I’m essentially by myself like 98% of the time now. Someone has to keep this economy afloat, and I might as well push the envelope as so many others are not. I do not mean I am not safe, but at the same time, I’m not going to wait to be vaccinated to date or be social.
With all that said, putting myself out into the internet ether again has its ups and downs. Here is a recent experience you may learn from.
Dating or Treating – That is the Question
So, I’m a guy, now 47 years old. When I decide to date someone years younger, I guess I expect some bit of imbalance. When I was dating women in their 20s, sure the Sugar Daddy/Sugar Baby stuff was apparent. Women in their 30s, though, I did not expect the same.
I got back on Tinder early on because frankly I have like zero success on Bumble. Hinge is good for me, too, but Tinder gives you great variety. About 2 months ago, I matched with an attractive woman who recently relocated to Chicago from the Bay Area. I always see that as an opportunity for a guy like me to show them the city, even in a pandemic. After some back and forth, we settled on a date to try one of the latest COVID crazes, an igloo.
An aside, the COVID igloo is kind of a mind trick. The regulation in Illinois says that you cannot have any “indoor” dining of any kind. You can however sit in an enclosed igloo with up to 6 people. Incidentally, you can also sit inside a place if they have their windows open and you are like 25 feet from the open window. To me, this is not a scientifically tested theory of virus spread, but for people like me who are willing to try it out. Hence, the rise of igloos, greenhouses, pods, and heated tents throughout the Chicagoland area is insane. Here is the site I check for the city to find new spots opening.
Now, one thing to note is that in the COVID era, restaurants are hurting. They have implemented a couple of strategies to stay open.
- Strategy #1 – Reservations. Almost every place is taking reservations, which supposedly is part of the Chicago regulations. However, a lot of places require either a Deposit at the time of reservation which will be forfeit if you do not attend or cancel 48 hours prior to the time. This locks in some element of profit given the reduced capacity.
- Strategy #2 – Timed Sessions. Most of the restaurants are timing you from the moment you sit down to the time you leave. Some places give you 90 minutes and others 2 hours, so they can turn the table and you have to not dilly dally.
- Strategy #3 – Increased prices. Drinks are crazy expensive now. It seems to me no matter where you go in Chicago, a drink is about $15. Yes, inflation is a real thing, but a cocktail at a pizza place versus a rooftop bar at a hotel are the same now. So, almost every date I go on is $150 minimum if you get 2 drinks eat and an appetizer.
Anyway, so I made a reservation in an igloo in one of my favorite neighborhood patios in Andersonville. I met my date with mask on outside, then when we got to our igloo, we were able to take down our masks to meet. She was lovely, and our first date was very nice. The hot toddies were delicious and the food was good. My date had recently come out of a relationship, so she was just slowly going on dates. Great!
On our second date, I found a really great activity. It was actually Thanksgiving Day, which seems weird, but I did not have my daughter and she had no place to go. I found this really cool activity called – Art on the Mart:
The show is a video projection of both artwork and photos on to the Merchandise Mart along the Chicago River. The projections are accompanied by music, and the show lasts about 30 minutes, which is perfect for a cold night. My date seemed to genuinely like the experience. Plus, we walked arm in arm, which I like. Afterwards, I got a reservation at the Upstairs at the Gwen (Hotel), which is the former Conrad Hotel. They had one of those open gas fire pits in the center of a table. Again, I had a nice time talking and getting to know her. We had a couple of drinks.
On 2 subsequent dates, I took her to the Jack Frost’s Christmas Tree Farm – a fun Instagram Trap then Parlor Pizza
Followed by a trip to Blitzen’s Pop Up Bar at Recess, more on that later.
Now, Tinder is like Sugar Baby central. Some women are very forthright with that desire. I’ve written about it before, let’s revisit the concept. Sugar Babies would like what is called a “mutually beneficial relationship” which is more transactional in nature. Typically, the Daddy gives an allowance, gifts and dinner for sexual intimacy. Again, I’m not against this in principle like some, but everyone should understand what is going on. When I dated younger women, I kind of expected it. And I guess I expected more out of women in their 30s. Shame on me. I do understand that men are still expected to pick up the check, and I’m willing to do so.
In this case, on our last date to Blitzen’s Pop Up, I want to set the stage a bit. My date was someone who when I sent texts, they would reply sometimes a day or later. Even if I was trying to set a date for the weekend, which to me was troubling. Plus, in the last 2 dates, my date kept me waiting upwards of 30 minutes in the car as they were getting ready for our scheduled with a reservation timed date. Understand that as mentioned above, the Blitzen part of the date was only 1 hour, and I had a second location lined up afterwards at a place called The Dawson. Again not just a challenge logistically, but it is also a timing of reservations, as COVID dating allows for virtually no spontaneity.
She finally got in the car, and I raced to the venue. When we arrived, I was surprised to see Recess was open also as a restaurant, so I could have made the reservation there after the “Pop Up” part of the date. So, after we checked in – 30 minutes late, I went over to the host station in the restaurant to see if I could match the other reservation, given we were running out of time and staying would be convenient. My date went to the restroom. I secured the Recess reservation, canceled the Open Table reservation at The Dawson and waited for her to come out of the bathroom.
When she came out and we walked around the rather unimpressive Pop Up – which was really just 5 or 6 fire pits that you could roast marshmallows on and still pay for drinks above the $25 entry fee, she told me that she really was looking forward to going to The Dawson.
I was a little taken back, as I had to juggle reservations, and ultimately, does it matter which place we spend time together? I, for one, would rather be in one place versus two, given all that it takes to get in nowadays.
Anyway, I apologized for canceling the reservation and was able to secure a new reservation at The Dawson 30 minutes later than the original time, as the original time was now not available. We did get a spot by the fire and roast marshmallows and had 2 cocktails.
During this portion of the date, she proceeded to tell me how guys seem to think that taking you out means they can have sex with you. Hmm….. Interesting statement. After all, we had been on now our 4th thoughtful date, and we had barely a kiss between us. She also asked me if I had gone on other Tinder dates, which at the moment I had not. She also said that it would take 3-4 months to be intimate, and that she hoped we could be friends. Again, not a very solicited conversation, but I think she was setting a boundary or expectation.
After I closed out at Blitzen’s for way more than expected, then we headed to The Dawson for a couple more drinks and some shepherds pie. The Dawson is a nice patio with a heated tent, however not inexpensive. The date was pleasant enough as the others were.
The following week I did not reach out to her, and I did receive a text on Christmas which I replied to. Then a day after my birthday, which I did not hear from her on, she unmatched me on the Tinder app.
What do I take away from all of this. Well, my take on the situation is she wanted to see the city, like I said originally. She was furloughed from her job, so of course she couldn’t contribute to the dates. However, the dates for her seemed to be: this guy is nice and generous, and I do not have to be really interested in him. I can not text or call and even critique the venue a bit, and I get to be treated.
I learned from this experience and others that if I’m going to spend my time and resources on someone – given how high the bar is monetarily and the effort it takes to plan and work through the logistics, then I damn better really like this person. I have even younger women that I can call and buy drinks for, but I guess I was thinking of more with a 35 year old woman.
She is a nice person, and I wish her well, but I’m not dating just to treat you to drinks and a good time. I do want someone who is genuinely interested in me or at a minimum puts out a little more clearly that we can go out, but this is going absolutely nowhere. Maybe she lost interest, and she handled it her way, but besides gaining knowledge of venues and COVID protocols, I probably could have just chilled at home.
Alright, hopefully, you learned a bit on this one. I have a few stories that are more fun to share in the coming weeks. This one just set the table for the COVID dating parameters.
Happy Dating!
Wegs
Well she’s a complete JERK! And next time take heed to, at minimum, the signs of one being ungrateful and flat out disrespectful. This is supposed to be the impression stage…with what she was displaying where can you possibly go from there???
Remember your worth & don’t settle-especially at $150 per experience.
Thank you, Shelly! You are my best advocate.