So, I decided to change the format of my posts going forward. I mean I’ve put out 21 rules for dating already. That is a ton. I’m going to put out advice here or there, still, as I am running into issues a lot of late. However, in the spirit of fun, I thought I’d share a couple of dating stories from my last singles stretch that still are entertaining.
Dating by Wegs: Throwback Edition
Story 1: Let Me See Your Grill
As I may have written about in the past, when I was between marriages about 10 years ago or so, I was an avid Match.com dater. In fact, my first marriage was the result of a Match.com meeting from back in 2001, yeah, that’s a long time ago. So, when I hit the dating scene again, I went back to the Match.com well. One of the appeals for online dating for me back then in my 30s was two fold: 1) As many of you know I tend to date women “outside of my race.” I prefer African American and Latina women. So, in Chicago, interracial dating is not as common as on the coasts, and as a result I was not meeting a ton of ladies I was interested in with my friends in the bars of Lakeview and Lincoln Park. Enter Match.com. 2) As a recent divorced dude with a young child part of the time, I felt like that information should be shared as quickly as possible. In fact, when I would go out with friends to the bars to meet ladies, it was always a struggle as to when to share that information. I suppose that is another blog post I should do some time. However for this post, I only state it that online dating allowed me to get the divorced and kid part of my life out there and let the potential dates make the decision.
With all that said, I went on plenty of dates back then. I think at my zenith I would go on 3 dates a week looking for that special someone. Now, back then, I was intent on a long term relationship, but of course, you had to meet and see where things went. Like the apps today, Match.com usually provided you with several photos of someone, which you can decide if you want to meet them beforehand. In this case, I saw the photos of a cute African American woman from the south side of Chicago, maybe 5 years younger than me. She was cute and fit, which were important to me. We communicated via email a bit through the Match system to set up the date. In this case, I chose to meet her at Lucky Strike, the large bowling alley located in the AMC Movie Theater in Streeterville.
Upon arrival, we found each other and greeted each other with a hand shake. We sat down in the bar/lounge area to get a drink and an appetizer. We started talking, and I couldn’t help but notice that my date had gold teeth. I mean she literally had a full grill of gold teeth. I was a bit taken back, as even in my experience dating black women, I had never seen that before. I don’t even know if I’ve ever met a man with gold teeth before. She was nice and all, but I guess the whole full grill made me feel like I couldn’t see her again. I was a bit more judgmental and quick to cast away people back then. I did review her ad after the date to see that she never did expose her teeth in the pictures, they were all half smile and more dramatic poses. Maybe she was trying to impress me or she was genuinely proud of that grill. Either way, it was too much for me at that moment. If that happened today, I probably would talk about it extensively to see what she was doing with one.
So, chalk that up to lack of due diligence and maybe even fear to talk about it with her.
Story 2: No Bumper, No Cry
In the same era of my single life, I worked at Bank of America in the retail banking centers throughout Chicago. My job was to converse with customers, and as a single guy in a suit, I was sometimes pretty overtly flirted with my female customers. From time to time, I actually went out on some dates with them, too, with mixed results. I mean the ATM was always an area to talk to your favorite women that came in the banking center.
One day, I had a conversation with a young Latina woman about my age who was very cute. It turns out, like me, she was a single parent, and an attorney living in the area – Lincoln Park. I was more than interested, and it seemed she shared an interest in me. We set up a date after work one Friday evening for our first date. It went very well. In fact, I really liked her and saw a solid future. We planned for a second date.
Now, date number two was at a place I love here in Chicago called Café Ba-Ba-Reeba. This place is a tapas place with good wines and just a fun atmosphere. I’ve been frequenting the place for years. We met there another Friday night after work for me, and in those days, I often had to work the next morning on Saturdays, which could lessen the possibility of a crazy night out. For this date, we started talking about our kids more. My date had a young boy about 10 years old at the time. She began telling me this story about how her son participated in a school sponsored, after school program at a park. One day, the park program staff passed out treats made with peanuts, I think, which her son was allergic to. He had a severe allergic reaction, which they had to call an ambulance. He was fine, in the end, but my date as an attorney sued both the Park District and Chicago Public Schools. Honestly, I was aghast by this. She sued for not only the medical bills, which seemed logical, even though I’m not sure she or her son told the program about his allergies. On top of that, she sued for and was awarded a free private school education at the school of her choice for the rest of his years in school until 18. I was completely dumbfounded, as I’m not a big legal guy. We had a bit of a spirited debate about the ethics of such a legal action, and for me, it soured the way I felt about her. Of course, I wouldn’t want any child to be in danger, but it seemed a bit egregious to get such a punitive judgment for a simple, ill-informed mistake.
Needless to say, after we finished dinner, I drove her back to her apartment intending to drop her off and really distance myself – ghost before ghosting. She lived in a complex in a pretty busy area, so finding parking nearby was a challenge. I pulled into her parking lot, and she insisted I come in for a beverage. I obliged her, but I’m not going to lie, I was not expecting much after our discussion. She told me to park in this parking space next to hers, and she assured me that it was ok. We went in her place, and she fixed a drink for me. After taking a few sips, I was like, “I need to go, I’m worried about my car.” She then kinda threw herself at me by the door. We kissed quite a bit, and things progressed. So, I was successfully persuaded to stay. She told me she would text her neighbor about my car in his space. I ended up staying the night after a passionate exchange.
In the morning, I woke up early at like 7 AM, after all, I had to be at the bank by 8:15 AM. I left the apartment to find my car was GONE!!! I ran back to her door, knocked furiously – “MY CAR IS GONE!!” She apologized and saw that the text message never went through the night before. We scrambled to figure out where my car was. She drove me up to Andersonville to the dreaded Lincoln Towing lot on Clark Street. I filled out a form to get my car. My date did pay for the tow, which was like $150. When I went to drive my car, my front bumper was barely still attached. I was furious. I screamed at the towing company – “What did you do to my car?!?” They said, “It was like that already.” More than likely, the tow truck hooked my car from the rear, but with a 1991 Acura Legend, the front was way too low to tow, and it probably dragged on the ground the entire ride up to the lot. I grabbed a complaint form, which I would have to file with the state.
I was able to rig the bumper to not drag on the ground as one side was still attached. I was beyond words with my date who was almost in tears. I’m sure I was less than a gentleman that morning, as I raced away to my house trying to get home to change and not be late to work. After work, I was able to get to the body shop, and the cost to fix the bumper was like $400. I remember calling my date in utter anger yelling at her about my bumper and how I would never talk to her again. I never did get a claim from the state against the towing company, but incidentally, I do think Lincoln Towing after years of this kind of bullshit has a major lawsuit against them.
In the end, this particular lesson was no matter if you are going to get some or not, trust your gut and just leave if you are not interested. It will cost you one way or another.
Hope you enjoyed these blasts from the past. I have a couple more gems like this from back in the day to share in the future.
Wegs