*Before you read further I suggest you read a past blog post to get a back story on who I visited in Chicago: What If You Knew How Long Your Relationship Would Last?

So my Chicago trip was, to say the least, …interesting.

I cried a few times after saying goodbye to Alex back in December. We had great chemistry and he treated me really well and made me feel special. I truly missed what we had. The day that I said goodbye I told Alex I would come to Illinois to do a date with him.

Sometime in June, I decided to make official plans. We caught up over text and I asked if I could visit him the following month. He seemed pretty excited to see me again so I quickly made trip arrangements.

Before Chicago

The Monday before I was supposed to fly out to Chicago Alex called me to figure out my itinerary. I told him when my flight landed and he told me another friend was also visiting him that same weekend. This friend was a girl so I was interested to know if she was “just a friend”, but I decided to wait to ask him details when I got to Chicago. He knows about my blog so he then went on to ask if I was planning on to go on a date in Chicago. He even suggested possibly doing a double date. I thought this was a little weird because I thought he would be my date? And why would he want to see me on another date when we use to date? 

A million thoughts ran through my mind after that phone call. I knew this Chicago trip had to be a good story to share no matter what, so I went into the weekend with an open mind. After getting off my flight I did some work while waiting to meet up with Alex after he got off work.  An hour and a half later we finally saw each other again. We hugged each for a good minute, glad to be in the same room together again.

Arriving in Chicago

We grabbed dinner at Panera Bread and just chatted about how our lives were going. I also asked for more details about his friend. Her name is Caitlyn. He said she was a friend from high school. Then he paused and continued saying they dated from freshman to junior year. Just as I expected…this friend was an ex. Of course, I asked how it ended and it was reasonable. He thought they should end the relationship before they went to college. She was coming in the following day so I decided to enjoy the time with just the two of us.

Meeting the Ex

The next day we enjoyed a great breakfast at Wildberry. We then proceeded to find a coffee shop to work remotely. By the time we finished working Caitlyn landed in Chicago, so it was time to finally meet her.  We introduced ourselves to each other and gave each other a friendly hug. The first hour together was a little awkward since we were strangers, but while we sat down and ate tacos at, Antique Taco Chiquito, we got along really well. I knew I wasn’t going to have an issue being friendly with Alex’s friend (ex or not), so I was glad there was no drama between us at all. 

Honestly, the biggest problems was between Alex and Caitlyn. They constantly argued like siblings. She was easily irritated by almost everything he did and he seemed to be purposely annoying her. I don’t like being around that kind of energy so it made me feel weird, but besides that, it was nice hanging out together. Throughout the weekend, we visited different restaurants, bars, and cool attractions in Chicago together. 

My Thoughts

During my Chicago trip, I was trying to figure out where Alex’s head was when it came to me. He was constantly asking about finding an Illinois date for my blog; we were hanging with his ex the majority of the time, and he described me to his ex as a girl that was writing a blog. Even when I admitted that I wanted to go on a date with him nothing really changed.

I think I planned this trip to Chicago because I was looking for closure. I’ve been holding onto the thought of Alex ever since he left. There were hopeful moments in Chicago when we held hands and times when my head laid against his chest. He moved to a different state for a job, so I emotionally thought me and him were still a possibility. 

The short time, Alex and I went on dates, I mostly appreciated him for his actions. He’s the guy that really taught me what I should expect from a guy and the standards I should hold. He consistently showed me how much he cared and wanted to spend time with me. Alex is still a caring friend, but this weekend his actions changed and so did my feelings…