Chronicles of a Yes Man: Rooftops, Bassments and Bathtubs

It’s been a little while since I have posted non-sports content on the Wegspool, so in the spirit of tapping into the Dating by Wegs posts, I thought I would do some posts on how my life has changed over the past 5 years. So, instead of pure dating life (although that will be included), I want to share my new found life experience as a Yes Man.

Chronicles of a Yes Man

So, what is a Yes Man? I’ve described myself as a Yes Man to friends a lot lately (and an Avocado Guy, but that’s for another day). When I look at my life pre-second divorce, I had moments of being a free spirit. In my younger days, I certainly took the road less traveled in doing the Peace Corps, chasing love in Colombia once and being a very early adopter of online dating when it was a foreign concept to most. However, in general, I was pretty reserved in my minute to minute choices. Being raised as a Catholic, I definitely have the inner voice or angel on the right shoulder that said – “You shouldn’t do that” or “Is that a smart decision?” I’m was no Saint then or now, but in this new iteration of who Wegs is in my life, I have definitely tried to embrace saying “Yes!”

Before I get into my first chronicle, I wanted to give credit where credit is due. When I first came out of my 2nd marriage during the early days of my separation, I met a very dynamic, young woman who truly changed my life. Did I fall in love with her? Of course, I did, but given the circumstances, I really was not able to pursue a conventional relationship with her. However, she was/is the type of person who literally could find the most insane fun I’ve ever experienced. In those early days, if she called to get together, I knew I had no idea what to expect except that it would be memorable. I remember one time we hit like 3 bars then ended up at a rave in some warehouse in West Town she told me to take my shirt off and just forget everything. This 45 year old guy sweating and swinging his shirt around with the youth of Chicago. She taught me how to say “Yes.” She challenged me in restricting myself based on my age or recent marital status or because I was a parent. It was my life to live, so I can choose to live it how I wanted to.

So, as a result, I have become perhaps a little irresponsible sometimes, but a much more fun and at peace person. I do not often seek out the chaos or foolishness that used to come with her in those days, but I’m open to what the world has to offer and that takes us to our first chronicle:

Rooftops, Bassments and Bathtubs

So, last Saturday was kinda typical these days. I was out a little late on Friday after a happy hour, but that did not stop me from getting up early to hit North Avenue Beach by 8:15 AM to play in the season’s first tournament. Ironically, I made it to the Beach before my partner, which is rare, and Team Shake n Bake competed amongst the elements and good competition – without the results we wanted. Still, I had plans to meet up with some volleyballers to hit a rooftop and then on to the now famous Esco Bar for some late night dancing. I got home, ate a meal, and took the essential disco nap to get ready for action.

Now, as I’ve written many times before, Chicago has the Seasons of Dating.

Dating By Wegs – The Seasons of Dating

Since the spring has been so up and down, I feel like the active dating season has been delayed a bit. However, in the past week, the match volume has hit a peak. After a longer winter/hibernation period, finally, Jimmy Wegs was getting some matches. In fact, earlier last week, I had a date during the week and had set up another for Monday. So, I decided to keep swiping while out on Saturday because – “Why not?!?” En route to picking up my friends, Lt. Calves and volleyball’s favorite yoga instructor in the Uber, we finally headed to the I/O Godfrey Rooftop bar.

First of all, the Godfrey is a nice spot. Their rooftop is atypical in the sense that it is really only the 6th or 7th floor of the hotel, but with the open roof, larger table areas and outdoor fire pits, it is a swanky one. Our yoga friend’s studio had a member event there which meant a sponsored table. Lt. Calves and I did just go to the bar to start getting ready with a couple Old Fashioneds. Meanwhile, I’m actively going through profiles on Hinge, and I matched with a real beauty. In messaging, it turns out she was just visiting Chicago from Austin for this big restaurant conference at McCormick. So, knowing, I did not have a lot of availability both with her short stay and not to mention my daughter was in town visiting, I decided to take a shot – probably fueled by that Old Fashioned.

“What are you doing tonight?” – I wrote.

“IDK what to do lol. What should I do?” She replied.

“I mean you can meet me friends out.” I messaged.

“Why won’t you be there?” She said (I’m an idiot sometimes on these apps.)

“I’m here I just mean I’m not alone if you’re cool with that.” I hoped and prayed.

She agreed to come!!!

As I waited and recounted the interaction with my friends, I’m sure they thought I was nuts. In all honesty, I was half worried, even though my Yes Man ways haven’t led to terrible situations. What if she didn’t look like the pics? What if she was mean to my friends? Will she arrive on time or keep me waiting?

I ignored all those doubts, sent her an Uber and in like 15 minutes, she showed up at the hotel. I met her downstairs, and I was met by this tall, gorgeous woman in a bodysuit and heeled boots ready for a night out. I could not have been happier. We hugged, and I showed her upstairs to the bar introducing her to my friends.

Now, she was arriving just as the group was transitioning to the next place – The Bassment (not Esco Bar as the group changed course) – which is also a fav spot of mine. We actually walked the 5-6 blocks with 10-12 other people from the event there. I was really impressed by her willingness to meet a bunch of random people, but also she was cool walking to the next place – I was a bit worried about that, but she took it in literal stride. We were able to talk and get to know each other. She has a catering business and was making connections at the conference. Her drive and ambition were as attractive as her looks.

Once we got to The Bassment after a stop at the ATM, it was completely packed. The music was booming and crowded was singing along. We made our way to the bar, and in the darkness ordered some drinks. She noticed from across the bar someone with The Bassment’s signature drink – The Bathtub – which is a vodka based drink that is served in this cute little bathtub with a rubber duckie in it including lemon foam. Of course, I took a picture of her with it for IG. I cannot confirm or deny if that bathtub (and duckie) made it into a purse or not as a keepsake. However, I really just liked that she was not pretentious and her calm vibe was really awesome.

We made our way amongst the throng of people to the edge of a private couch area of the dance floor where we talked and danced for hours. We even made some new friends that had come in from Houston for a wedding that found this spot on Yelp. They asked her how she found it, and she said – Jim knew it – it got me thinking about another website endeavor actually, but I think my credibility just went up.

Anyway, as the night passed and my friends left, we were at the bar enjoying each other’s company. Another small crew of Vballers rolled in at like 2 AM including my guy and co-announcer to the tournaments, Karlo, so I knew were were in the right spot. He is always hitting good late night venues. However, about 2:45 AM the lights came up, and we didn’t have to go home, but we had to get outta there. I found a late night diner, Griddle 24 that is open 24 hours.

We headed there for some late night eats, which I rarely get these days, but “Say Yes,” and more conversation. When I finally put her in her Uber back to her hotel, it was 4 AM. I ordered my Lyft home (I can’t figure out how to order 2 Ubers at the same time). I was in a definite chill and happy space, even if I was exhausted. I had a man come up to me after she left and ask me, where he could meet a beautiful woman like that. I did feel pretty damn luck that the night worked out so well.

Come Sunday, after some much needed rest and fluids. We did communicate during the afternoon. She wanted to go out again. I was chilling, but when her post-conference nap turned into 3 hours, and it was pushing 9 PM on a Sunday, I had to question my Yes Man status. Still, I got in the car, and picked her up because why not, right? We hit the West Loop this time – first Bodega Taqueria y Tequila – right before they closed after 10 PM, which she enjoyed it given she’s thinking of a food truck in Austin. Then, we went on to Moneygun, another one of my favorites (that is still open late on Sundays).

https://www.moneygunchicago.com/

The Chef from Austin and I did it again, closing down Moneygun this time at 2 AM on a Sunday night. We were able to share more about ourselves the second night. Her ease in being herself with me was very comforting, and where I am right now I do feel truly my authentic self. I dropped her off knowing I would not see her again in Chicago, but with hopes of seeing her again either here or in Austin in the future.

The Yes Man came through for sure, but unfortunately, even this Yes Man makes mistakes. I mentioned I was on a bit of a hot streak on the apps. I also mentioned I had another date on Monday with someone new, in Chicago this time. So, as I do, I am a text deleter. It’s really my OCD side of me I guess. I like a clear inbox at work and on my text screen so I can keep things together.

Well, on Monday, I was texting both women – Chef Austin and my previously scheduled Monday date. At one point Chef Austin asked me how my day was going, and I replied as if I was talking to the other person – saying something like – “I’m excited to see your beautiful smile later.” Then, I realized I messaged the wrong person. My stomach dropped as if I was on a rollercoaster. After deliberating, I edited the message to her, but I still felt terrible about it. So, I came clean and apologized for the text. She did respond, but I’m pretty sure my chances of anything longer term are done. I flew too close to the Sun.

Still, I can confidently say that saying “Yes” in the moment to meeting Chef Austin made my weekend. I really enjoyed what felt like 3 dates in 2 days with her. She’s as ambitious and hardworking as she is stunning. I wish her luck in everything she aspires to do.

Oh, and the other woman ended up canceling our date on Monday. Lesson learned, Yes Man!

Wegs