Dating by Wegs: We Want Pre-Nup

I have been woefully inconsistent in my dating posts of late for a lot of reasons. The fact is dating in COVID has been rough. I have had a few other disappointing experiences lately anywhere between cancelations because the 2nd vaccine dose knocked out one date to women who haven’t broken quarantine in 5 months. So, needless to say, it has been a long cold winter in the Chi for Jimmy Wegs. Still, I have been holding back this little ditty, which is not really a direct COVID story, but it did happen during this time.

We Want Pre-Nup

The once great, before he went completely insane, Kayne West wrote a ballad that all men in their late 30s and above need to listen to really carefully. That song was called, Gold Digger. I actually love the song. I mean it has an incredible start an old school riff, then Kanye’s lyrics are smart, funny and spot on. In my experience over the near 3 years of dating again, I have come across ladies that want to be taken care of, which I do not think there is anything wrong with. In fact, naturally, I’m a caretaking, supportive man. Yet, Kanye had it right, when late in the song, the chorus of gents says – “We Want Pre-nup, We Want Pre-nup.” For those that don’t know what that is, that is a Pre-Nuptial Agreement between spouses, which protects the assets and future financial standing of the parties. Admittedly, I never imagined getting one with either of my 2 marriages. In my first marriage, we were of very equal income levels, we had a child together, so child support was part of the divorce, but we did not raid each others’ assets. In my second divorce, unfortunately, the marriage was not about money, but the divorce was all about it. Between the attorneys and the settlement, I lost 80% of my meager retirement savings to pay for everything. So, yeah, Kanye, “I Want Pre-nup!!”

On to the actual story now, I saw someone on Bumble that I used to work with. It was a beautiful younger woman who I had a crush on. When we matched, I was genuinely excited about her. We messaged, then talked on the phone, and then set up a date. To be honest, I wasn’t entirely sure she was interested in a dating relationship, but I wanted to take a shot. We met at a nice spot in the city that had an open rooftop thing, and I had a nice time reconnecting with her. She was between jobs with the pandemic, and she had been in NYC for a while. Now, in that first conversation, which I thought was more like friends talking, she asked if I would ever get married again. The answer I always give is – “Yes, if I meet the right person, I am open to marriage. I don’t need to get married again, but if I do, then I would want a prenup given my recent experience.” So, yeah, maybe on a first date, you shouldn’t throw a prenup on the table right away. However, if you are going to talk about marriage, then I think it is fair to talk openly about your needs. I didn’t belabor the point just talking to a friend about how I see my path. Incidentally, when I went out with another woman, a doctor, who probably makes 2 or 3 times what I do, she replied to that statement, as “I absolutely would want a pre-nup.” So, it is not out of the question to talk about prenups on dates.

Anyway, we had a nice time. I thought there was some romantic chemistry, so let’s keep it rolling. I liked her, so why not?

We ended up going out another time watching football on a Sunday for brunch, too. It was fun. Now, I should also say that my date right about the time we started talking had started to watch her 15 year old sister. It was a real adjustment for her as a parent-like situation. We talked a lot about it. In COVID, she had to adjust to having her sister do online classes and discipline like any parent would. I respected it, so availability was a little tougher on dates, but I was willing to work around her schedule. I say all that, and the next time we were supposed to hang out after 2 dates in like 3 weeks was tough. Halloween was upon us, and as most of you know, Mayor Lightfoot locked down the bars, clubs and restaurants for indoor dining. On that Saturday, I struggled to even get a table at Ranalli’s with my football team after our game, so when she wanted to come with her sister, I was like – I’m not sure we can get you seats at this packed patio. Maybe that was fortunate, as a few days later, she told me that she and her sister both contracted COVID and would be down and out for a while. Bummer and my first direct dating contact with COVID at that time.

I checked in on her, and she intimated she wanted me to send flowers to her, which I did not. Still I was keeping in touch. A couple weeks later, I was trying to see her. Plus, we had been talking for about 6 weeks now, and we hadn’t even made out, which for me is a thing. Given the COVID restrictions and changing weather in Chicago, I invited her to come over to order some Thai food – a Netflix and Chill type date. Did I intend to make some moves? Of course, I did. However, I wasn’t sleazy about it, and she had said she liked Thai. She told me should could come over if her sister could come……… I said, “Umm, I guess that’s ok.” In my mind, I did want to see her, and if we were going to be serious then this sister would be part of it, even though my “chill” part of the date would not be fulfilled. Then, she said, “We are going to be wearing masks, just so you know.” I was like – “Huh?” Weren’t you two the ones with COVID already. I was not about to have them come over and wear masks in my home. So, I told her that we should just wait until a time when we all felt safe.

Honestly, I was getting disinterested at that point. If we were not able to spend time together and get intimate at some point (even if that is just making out), then what am I doing here? So, I just went about my week. On Friday of the following week, she called me and asked my plans for the weekend. I actually had a date that night and had plans with friends on Saturday, plus dinner with my mom on Sunday, so I was busy. She seemed dejected. After the call, I felt bad. I texted that we could go for a walk on the Lake on Saturday, which to me was both safe from a COVID perspective and no pressure for sex, which I was sensing. She told me she had brunch plans, so I was like – ok whatever.

On Saturday morning, I was going to sleep in. I had a solid first date with the other person, so I was chilling. Then, she called me at 9 AM. I answered in complete surprise. She told me her brunch was canceled.

I’m like, “So do you want to go walking with me now?”

She asked – “Was there food involved?”

What?? I responded, “There can be.”

Mind you, I was in the middle of a walking challenge at work. I had to walk another 10 miles in 2 days, so walking was my priority. I agreed to buy some food at a local brunch spot, and we can eat it at my house then go for the walk. This chick wanted 2 full brunch entrees – Red Velvet French Toast and Crab Cake Benedict….when I asked if she wanted something to drink knowing I had literally nothing in my house like coffee or juice.

She said, “Mimosas?”

Ugh, whatever, so I woke up, showered and ran out to buy a bottle of reasonable champagne and orange juice, since the brunch place did not service alcohol.

When she arrived, I poured her a mimosa, we started eating. She wanted me to drink, too, which again, I’m like we are going on a WALK, but I had one. Then, she wanted a refill. When I pushed to get to stepping, she asked to take a Roadie…. She made a 32 oz mimosa in a large straw cup I had from my Vegas trip. I knew this was going to be interesting. We started walking, and of course, she wanted to take selfies about a mile in. Then, when we got near the beach after finishing the entire 32 oz, she took off her shoes and socks to walk on the beach in the water – IT WAS 42 DEGREES OUT!!! At least, we were going a lot further than I thought. After coming back around, we walked by the harbor, and the date, which was on the annoying level went a different way.

In seeing all the boats getting taken out of the water, she said, we should buy a boat. A what? I’m like those boats cost like $100K over there. She’s like just a little boat – like $5K. I proceeded to tell her how boats and horses are two losing propositions. I told her a story about a friend and the real costs of the boat, and she wasn’t getting the hint. At this point, we are 2.5 miles from the house, and this woman had the equivalent of 5 mimosas. Well, the inevitable happened, where she had to pee with no bathroom in sight. So, she had to find a spot behind a garbage can to relieve herself. It was actually pretty funny. She was embarrassed, and I told her that this blog post is writing itself.

The rest of the walk back I made the mistake of talking about my job. I was telling her the differences between my old job and the bonus structure at my new one. That was a mistake, since she spent the next 15 minutes telling me how to advocate for a bigger bonus. Even when I told her straight up, that I am not ok talking about this with you. She droned on, and I had to completely shut down the conversation. When we got back, I was like – well maybe she will want to hook up at least to salvage this date.

We were sitting on the couch, I had my hand on her thigh. Mind you, we still had yet to even kiss yet. I was not making a strong move here, just chilling in my space, as typically things can heat up quickly at this point. When my date said –

“I really want to talk about the pre-nup……..” What in the fuck!?!

“I don’t think I should be punished for someone else’s actions……”

I took the next 15 minutes defending my position on the prenup, and honestly there has never been a conversation in a dating situation that has ever made me less interested in sex in my life. She left, and I was like – See Ya!

About a week later, I did text her on Thanksgiving, which was probably a mistake. She called me on the weekend and told me how last week she was struggling with her sister going back to her mom, and so on. I let myself feel bad for her and give her another shot, in my mind until she started to ask me what I was doing for my birthday. My birthday is December 27th (a rough date), and hers is Christmas Day.

She was like – “We should go to Mexico!” I was dumbstruck.

I responded, that I would have to think about it. She wanted a deadline, and I said, a week….. I had no real intention to think about it. I mean I can deal with all the silliness, but clearly I misjudged this person and their intentions.

The next week I worked about 60 hours and didn’t think about much else. I did not text or call. Then, on Sunday night after another full day, she texted me, basically questioning if I was still interested and that it was strange how I just disappeared in a very terse way. I followed the old Michelle Obama method, when they go low, you go high. I told her that yes, I was less interested, but I would be willing to talk about it. Plus, I worked 60 hours this week including 8 hours on Sunday (today). We communicated a little more here and there, but I was done pursuing her, especially since she never really even asked why I was losing interest. Frankly, I was really disappointed not just in her, but in myself. I can deal with a lot of silliness – I don’t care if you get buzzed and all that, but when things just come down to money, especially when we haven’t even been intimate at all, I think the writing is on the wall.

So, as I write this on a Friday before a holiday weekend, I can say that I’m happy to still be single. There is nothing wrong with protecting yourself and putting out what your true needs are because unfortunately we are all very self-interested people who will look to meet your own needs over the other person especially early on.

Enjoy your weekend.

Wegs