Learning to Fly… On my Own

I was so excited for my date with Sean! The entire week leading up to the date there were consistent messages, funny debates and even a few really sweet messages that made my heart jump. It was a a reminder of why I love to date and what I want in my partner.

My all time favorite moment  was a particularly rough moment at work when my anxiety was soaring high! I think everyone knows at this point in time that this is both an issue for me and a way to my heart.

I  replied to Sean after he asked about my day “rough day and I’m struggling with some anxiety. Don’t worry I’m working through it though!”

This is what I do… my MO. I will let you in for a brief second and then immediately follow it up with you know this won’t be your problem. I’m cool..I’m cool. Not your problem. I’ve got this! I’ll fix this!

Most people will send a line or two like “You’ve Got This!” or “Don’t worry the day is almost done”. Both of these replies are good and perfectly fine. Most people don’t know what to say to that and I’m really good at downsizing my emotions.

However, Sean replied back with a full paragraph. An actual paragraph. He lead with what a rockstar he thinks I am, that he understands it can still be rough and that he’s here to support me if I needed to chat. It legit made me tear up a little bit. He saw through the bullshit. That was huge for me. Not that I don’t need to stop the bullshit but sometimes we all have walls. It was a moment. I felt safe.

Then came Friday. I hadn’t heard from in the morning and got a little worried. But not too worried. I could tell he was in to me and I was totally in to him.

There was a joke that the guys on the podcast always say “Jill, you’re a bear with a net chasing after the men.”

Sean would say to this joke “Jill put away the net. I’m right here!”

As we got later into the morning he messaged me “Don’t worry I’m not flaking! I’m just really busy at work. Can’t wait for tonight!”

As the clock struck 5pm I legit stared at the clock, trying to play it cool. However, I drove quickly home to get ready! We had planned on going to an arcade bar to eat sandwiches, drink beer and play each other in games. I  wanted to look casual but low key perfect (not typically a combo but it matches me right!?!)

Picture taking at the same place

We messaged back and forth and I started to get ready. After a few minutes of  doing my hair I called him. I had a question and didn’t want him to text and drive. It was legit a silly question and could have waited but I couldn’t wait.  I forgot how hot his voice was. I remembered our connection, our conversation but forgot his voice…Dayum dat voice doh!

We joked on the phone for a while and he was clearly on his way. I could hear the wind behind his voice and a faint sound of the radio. He was about an hour away and I could tell he was feeling it just as much as I was. It was nice to not have to second guess myself or how I felt. I am not sure if that was his confidence or mine that caused that comfort. I’m starting to believe it was mine or at least a combo.

So after a few minutes after our phone conversations.. Okay guys there were a couple… what can I say? I’m a little weird and love to chat on the phone. I’m an older millennial… so not to the norm! Plus that voice…

So a few minutes after the last call I got another long paragraph. This time it started with “I’m sorry I just can’t do this…” and ended with a lot of reasons why we were different and why it just couldn’t work. It didn’t make any sense. I thought it was a joke.

I immediately picked up the phone and called Sean. Sean confirmed he just couldn’t do it. It wasn’t me it was him. My eyes were starting to turn hot and the tears were coming down. I just didn’t understand it. I missed it. How did I miss it? I had no idea.

I ended the call quite abruptly because it didn’t matter what he said… I wasn’t listening and I felt the message was the same “I’m just not that into you.”

I spent the night in, watching The Office, and feeling oddly weird like a break up. This break up was with a guy though I only knew for a week. I told myself all kinds of stories.

Clearly I’m not meant to have these moments… Maybe I was meant to just be alone… Maybe I was meant to help other people with love but not have it on my own… Why do I keep trying? … I knew I shouldn’t get excited, I knew better than that. It was my fault for letting my thoughts get the best of me…. I shouldn’t have called… ugh! Why did I call? 

It was a little dark but was short lived. The dark thoughts came and went and then left. I went to bed and woke up even more confused.

That afternoon, I sent Sean a message. I apologized that I came on so strong and probably applied so much pressure to him that he panicked.  He quickly messaged back. It was all super nice things and how it wasn’t about me. It was actually about him. Of course I didn’t believe. I had heard this before. Plus it is really hard when you strive to take accountability for your life to know when your accountability ends and someone else’s begins.

After a while he told me the actual issue. He came to that bar for a few drinks and ended up falling for me. The past week had been amazing and the excitement I was feeling he was too. However, he knew it would end and would end badly with a lot of hurt.

Sean told me had been  diagnosed with Borderline Personality Disorder.

He told me this manifested in his relationships mainly. They started with a surge of love and ended with him having resentment. He would find small things that would make him question their love for him This would eventually end the relationships in a lot of pain and hurt feelings. He knew he hadn’t done the work needed to give us a real shot.

It was such an honest and vulnerable moment for the both of us. I was so grateful that he shared it with me (and subsequently said I could share in this blog).


My first reaction to him was “I can do this!” I have dealt with something similar in my past and knew that I had the fortitude and understanding to “get through it”. I was really surprised at myself for this instant reaction. I tried to convince him that we could work on it together. He knew we couldn’t. This was his work. (Please note all of these reactions and feelings were in the span of an hour – maybe two. The build up, revelation, we can do this and quick research in between)

It was after our final goodbye that I actually took the time to look in to it. When I did and read the treatment and steps needed  I realized how independent that growth was (it always is). It  brought back memories and feelings of previous relationships I had. It was something that while I could get through again, I never want to. I truly wanted better for myself and my future.

It was then that a peace came over me. The closure I needed from that conversation wasn’t with Sean it was what I needed to learn for myself. It’s funny how the universe throws life lessons my way. This guy HAD to be a guy that I really liked in order for me to truly understand that my care for myself was more than my desire to be in a relationship.

I could have just as easily messaged Sean a few days later, said that the build up and 10 months would be worth the pain, that I knew that we could go to counseling and figure it out, that I was strong and could get through it, and that together we can work on this.  I had done this for a long time. I knew this story. I had lived this.

Instead I read, I felt and I moved on with my head held higher.

I came to an even greater appreciation for myself and for Sean. I was attracted to a man.. a true man. A man that showed compassion, genuine care for me and showed me the potential of the guy I want in my life. A guy that told me the truth when it would have been more convenient and fun not to. I will truly be grateful for that week of magic and look forward knowing I will find it again ♥



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