Six hours and 153 miles - totally worth it

Written 9/7/2025

I had my first “second date” since 2022 yesterday. I wasn’t sure if it was going to happen. I do know wonderful redhead enough that I can’t push her to nail something down. It’s up to her to make that decision.

I had planned my Saturday out without her. I was going to ride my motorcycle to pick up a raffle prize I had won. Go to Theosofest at the Theosophy Society, then test ride Indian Motorcycles at IMotorsports.

Then the text came in about going to the art fair in Wicker Park.

Plans changed…

I scheduled picking her up at 1:30 pm as that gave me enough time to finish some projects I was working on, including picking up the raffle prize.

I met her at her house. It was my first time there. A beautiful house set on a corner lot. Her son opened the door as she was drying her hair. I played with her little dog while I waited and then she came down the stairs.

Yes, I’m infatuated with her. She’s really cute.

We set off for the city. Her childhood friend was exhibiting, and we were going to say hi to her. It was a great excuse.

I opted to pick her up as it, selfishly, gave me more time with her. Plus, coordinating meeting in Chicago sucks. She had been going non-stop and I wanted to make it such that she didn’t need to worry about anything.

An hour into the city while we talked and laughed. At one point I had to go around a yahoo who was just stopped in the middle lane deciding whether to turn left or not. Wonderful redhead spouted off exactly what was in my head (I was on my best behavior). It was awesome.

We parked and then found her friend, whom she hadn’t seen since 7th grade. It was a joyful reunion, I took their picture, and they chatted. Her friend makes some unique art pieces of cities and places she’s been. She travels the art circuit in the summer to make money and avoid the heat of Arizona, which is where she lives.

From there I took her hand, and we looked at the other booths. We bought perfume together from a local guy. We then grabbed a drink and food at Little Victories and went exploring, ending up at a kitschy little place called LeMidi where we ate cheese and drank wine (I actually had a ginger lemon basil soda since I was going to be driving soon).

What an amazing day. It’s been a long time since I was with a person where I laughed so much.

Then it was an hour home.

Six hours with her. 153 total miles driven for our date.

Totally worth it.

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