Anyone who’s been following the blog for awhile might remember me – Pablo X. I wrote for the blog a couple of years ago but stopped after life got in the way. I recently reconnected with MB, the creator of this site, and it turns out he was planning a trip to Chicago, where I live! We decided we had to make a meetup happen. And after hanging out weekend, I’ve decided to start writing for MB again! Look out for more posts from me in the near future. In the meantime, here’s a quick rundown of our weekend.

MB had been in Chicago visiting his friend and had the night free on Thursday. I had an early morning meeting on Friday so I couldn’t stay out too long, but we decided to grab a couple drinks at a cool bar I know. We’d never even seen pictures of each other so I told him what I was wearing and walked into the bar, where he was already enjoying a drink. We found each other pretty quickly and I must say, MB is a good looking guy! Totally makes sense why he has so much success with women.

We caught up over drinks for a bit – an old fashioned for me an a vodka tonic for him – before he initiated the first approach. There were a couple of girls sitting next to us at the bar and he leaned over and talked to them. Not much response from them so we went back to catching up and finishing our drinks.

The bar was starting to get more crowded so it was time to do a lap and see if we saw any sets to approach. We got another round and saw a three set around the corner of the bar. Two of the girls looked like they were in college, and they were with an older woman, probably in her late 30s. One of the college girls was very hot, but it was hard to tell at first because they both had on big sweaters, appropriate for the arrival of the cold weather in Chicago. The other college girl was cute as well, but less so than her friend. MB opens the set and I join him a few seconds later.

They were visiting from out of state for a concert, but the concert was cancelled because the performer was sick! What a disappointment. We chatted with them for a bit, but the older woman made it hard to flirt with the college cuties. I didn’t catch how the older woman knew the college girls, but in any case, the energy started to die down so MB and I bounced from the set.

We chatted by the bar for a bit before we saw another set. Two older women, probably in their late 30s but still quite attractive. We approached them and made a bit of small talk but at first it seemed like they weren’t super into it. They told us they were in the middle of an intense conversation and would come back and find us when they were done. I was ready to bounce but MB’s skills saved the day. He got them to open up to us and share what this intense conversation was about – and it was quite a story!

One of the women had just found out two of her coworkers were having an affair, and the man had just left his wife! Not only that, he had a newborn baby at home! The two women at the bar were discussing how to deal with the situation and downing some drinks to take the edge off of the stress that situation was causing. We had a fun time chatting with them, but I think both of them were a bit too old for MB and myself to pursue any further. Plus I had an early meeting to wake up for. So we finished our drinks and called it a night.

The following Saturday, I had a free afternoon and MB wanted to make the most of his last day in Chicago. We met up for pizza and beer at local joint, and he did a few approaches while I waited for the always-delayed CTA train. We had a great conversation over our pizza and beers. We see the world in a very similar way when it comes to dating, politics, and careers. Which is no surprise considering I liked his blog enough to want to write for it!

We were both feeling pretty full and buzzed after leaving the bar, but decided to get in a couple approaches while we could. The arrival of the cold weather in Chicago meant the streets weren’t as crowded as they would have been in the summer, but there were still a few good sets out and about. MB approached a very cute European girl and ended with a number close. Then we stopped for one more drink at a heated outdoor spot. A couple more approach attempts were made, but we were both feeling pretty buzzed by that point.

So we decided to end the night at a classic tavern with amazing bar food. MB’s friend joined us for dinner as we chatted about life in Chicago, careers, dating, and family.

All in all it was a great time! Look out for some new content from me coming up soon. I’m excited to be back!

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