It’s been a couple weeks since an actual dating post. I apologize with winter, work and the big Match Marker Event – I’ve been swamped. Still, like in dating, you have to keep trying.

Dating By Wegs

Rule 17 Live In the Moment

I think when you are younger naturally you just go with the flow. I mean who knows what tomorrow brings with your love life, career, and even life in general. As you get older, you think you can control your life. You work towards a goal, settle down, buy a house, and life becomes predictable. There is nothing wrong with predictability. I mean I like getting that paycheck every other week. However, in dating, can you really look beyond this very date or moment?

The truth is if you are like me, you are pretty clueless on what people are thinking in a given moment. I’ve definitely misread a lot of situations when I thought my date and I had this incredible time and then I get ghosted. So, reason one for living in the moment of the date is there are no guarantees of a second date. As much as you may feel connected and dialed in with this person, the only thing you can control is that very moment. So, make the most of it.

Another reason to live in the moment is that circumstances change. Maybe you have a sick relative or you lose your job or any number of life changing events. We only live once, and we cannot anticipate those changes. A life lived with those crazy and fun moments between those difficult times is what gets you up in the morning or for me gets me to try dating again with someone new. We are only single for a finite amount of time (even if I’ve had a few stints), and life will change. Therefore, why not make the most out of this very unique period in your life.

On to the story, this entire post is kind of a veil for a personal experience. Thanks for bearing with me here.

So, I’ve been dating/seeing/experiencing someone who is much younger than me for several months. To be completely honest, I adore this person, but given that she is so much younger and her situation is not very conducive for an actual relationship, I’ve accepted whatever contact I can have with this person. Now, beyond her being a knockout. She has taught me over the past few months to truly live in the moment. It’s been fun to meet her out late night some times or go on some random adventure. Of course, I want a future with her, but I’ve tried to stay present to just enjoy what time we do spend together.

A couple of weeks ago, I had one of those weekends that I literally had no plans. It was an awful weather weekend with snow and cold, so on this Saturday night, I could have literally been asleep by 9 PM. Instead, my friend and I were texting back and forth, as we do often, at like 5 PM. She was at a bar in Lincoln Park, and she was like, “Do you want to get ribs with me?” Now, most of you know, I don’t eat a lot of meat. I’m a pescatarian at best, but in the past couple years, I’ve been open to trying more things. So, having an opportunity to spend one on one time with this beauty was a no brainer. I picked her up in the terrible road conditions and headed to our venue.

Green Street Meats

https://greenstreetmeats.com/

My friend wanted the Beef Rib from Green Street Smoked Meats in the West Loop. Once I found a spot in the sloppy snow, I met my friend who secured a place at the bar. This place was incredible – like a large former warehouse space with cool stringed lights, picnic tables and a serving line for the food. We grabbed a cocktail and then headed to line to get the Beef Rib which is like the rib given to Fred Flintstone in the opening credits, some brisket and a bevy of sides. We hit a few different sauces and back to the bar for a delicious meal. Beyond the food, my friend and I had a great conversation. I mean I’ve known her for months, but it felt like our first legit date. I’ve liked her for a while, and this date solidified those feelings. We finished a couple more cocktails, and then my friend is like “Let’s go to Joy District.”

Nothing Like Bottle Service

https://www.joychicago.com/

My friend has a lot of friends in the bar business. So, she knew the bartender at Joy District which is a night club located on the busy Hubbard Avenue corridor in River North. I had met her friend before, and the best part was discounted drinks. My friend and I continued to enjoy our time together. It was like 9 PM, so the place was pretty empty besides some Russian dudes watching MMA. We had a shot or two with them, and as the night hit 11 PM, I felt like I needed to go home (after all I drove). My friend asked me to bring back her phone charger that she left in my car. So, I pulled the car to a loading zone, ran in with her charger and to say good bye. Now, I am a sucker for this girl no doubt. So, when she asked me to buy her and her friends a bottle (bottle service), I was like – “Sure!” All I really want is for her to have fun.

After agreeing to the bottle of Green Apple Circoc, which I knew was pricey even if discounted, I turned to her and asked her, “Do you want me to stay?” She said, “Yes, I want you to stay!!” I was elated. As I said, I’m into her, and why let this night end, right? I re-parked the car to a place that could stay overnight.

After about 20 minutes, her other friend arrived, who I had met before, with 3 other young women. We had the back bar locked down, and out came the sparklers and all the mixers. It was a party. Within minutes, the ladies were up on the bar stools dancing, I may have dropped it to the floor a bit myself. My friend and I were growing more affectionate, and at one point, she turned to me and said, “We need to do this every Saturday, just not spending so much money!” I actually couldn’t agree more. I was having the time of my life surrounded by these young, beautiful women and really connecting with my friend. Of course, we ordered another bottle. It was an incredible night.

After the 2nd Ciroc bottle, a bottle of champagne was being passed around, which I don’t quite remember ordering, but whatever. Things were still good, until, they weren’t. At one point, I turned around and my friend got sick. I was in a daze. The girls rushed to the bathroom. I got the bill, which was like $1000 – whoa! She came back up, and we had to leave. I do not condone drunk driving at all, and to be honest, I was very lucky that night. In my non-sober mind, I needed to get her home and not in an Uber where she could get sick again. So, I pulled the car around and scooped her up.

When she got in the car, she said we had to pick up the other girls who her friend had gotten her car towed. So, I picked up 3 of the other ladies and headed to impound. About a block after picking them up, one of the girls on the right side in the back, also got sick as the door opened in the cold night. Another block later, the girl on the left in the back got sick out of the car. It was chaos.

I got the 3 ladies to the impound lot, and hightailed it out of there with my friend who was feeling better. We got home safely, and she passed out at my place after 3 AM. What a crazy night!

In the morning, my friend wanted to go home. It was like 9 AM. I gladly took her home, but much to our disgust found that the back seat to the right was soiled by a fair amount of vomit and it smelled…. I took her home, as she ran out of the car to safety.

I spent the next hour cleaning the now frozen vomit from my car in the 5 degree temperature.

Ok, so some are going to say, that’s why I don’t go out like that or that’s why you can’t date young women. Well, to me, it was still an incredible night with someone I really care about. We have been able to spend more time together since then. However, unfortunately, my friend has decided to move back to California to be closer to family. Admittedly, I’m crushed, but it is what is best for her. In retrospect, I couldn’t be more happy that we had that crazy night and have connected more lately. Like I said, you don’t know what tomorrow will bring, and if I decided to be predictable and stay home that night – no blog post or great memory (or massive credit card bill, but alas).

So, to quote the great Vince Vaughn, “Go make some bad decisions!” Maybe not drinking and driving (which I Ubered the last time we hung out), but take a few chances and truly enjoy your night whether that is a great conversation over dinner or a walk on the beach or night in the club. You never know when that music will stop.

Wegs