The Story of Us: The One Where She Didn’t Kiss Him

She was sitting on the couch. It was Wednesday at about 10pm and she was just scrolling through social media when she received a message.

And who was it from? You guessed it! Matlock.

To her surprise, he was coming to Chicago on a business trip and he remembered Kelly lived in Chicago. So, what better person to ask about what to do in Chicago than a Chicagoan herself?

Kelly of course gave him a long list of typical tourist activities and some fun not-so touristy things to do. But, she knew she wanted to meet him. So, she took it upon herself to offer to show him around the city.

He of course said yes.

Fast forward to Friday evening. Kelly took the train to downtown Chicago and she was surprised that she wasn’t nervous to meet him at all – although, her mom was definitely concerned that she was meeting some boy she met off the internet 😅

She got off the train and walked about half a mile to the hotel Matlock was staying at. About 100 feet away, she saw him. Leaning against the brick building, cigarette in hand. He had that cool, kinda badass vibe. As Kelly walked towards him wearing all black with her Calvin Klein peacoat, leggings and leather boots, Matlock only had one thought:

“Damn. I’m in trouble.”

They chatted for awhile and decided to hit up Starbucks first (clearly, things haven’t changed too much since we go to Starbucks practically daily!), then they went straight to Eataly – an awesome, two-story Italian market. As they walked around in awe and checking out all the cool Italian food and knick-knacks, they decided to pick up some proscuitto and accidentally left without paying 😅 (Don’t worry – about half way down the street we both realized what we had done and went back to actually pay!)

They then went to Pizzeria Uno for some classic Chicago deep dish pizza and red wine. They strolled the streets of the Gold Coast talking about their lives. Kelly was impressed with how many places Matlock had visited in the world – from Australia to Canada to Mexico to Japan, he’s been practically everywhere! And Matlock admired her dreams and work-ethic.

While it wasn’t technically a date… they came to terms with the fact that this was most definitely their first date. They had their first red velvet Sprinkles cupcake, talked about raising kids, and ended up at the Purple Pig sitting near a window at a small table drinking red wine and talking about their lives until they closed. Well, to be honest, they (politely) told us to leave since we didn’t realize they were cleaning and putting the chairs up 🙈

As they walked back to Matlock’s hotel at 1am, the night was coming to an end.

Kelly knew Matlock as going to go back to Florida and they may never see each other again. She didn’t want to get attached… So, instead of kissing him goodnight, she gave him a hug and said… “it was nice meeting you – I had fun!”

As she got into her taxi, palm to forehead – she couldn’t believe she had said, “it was nice meeting you.” She thought for sure they’d never talk again.

For Part 1, click here!

Stay tuned for part 3!