My Dating Story

A day in the life of James Cavanaugh - or a few

My Dating Story

Where to begin.  

I’m burned out. 

Before I get there, you may need some context.  I am ‘recently’ single, so there are definitely instances where I don’t know what I want.  I’ll be the first to admit it, and a lot of what I have done over the past 2 years has been figuring out what I want.  Sounds easy enough, but it’s easier said than done.  

2 years you ask? Yes, I was married.  In fact, I was with the same woman for the majority of my adult life.  We started dating when we were 17, and we were together for 10 years prior to our marriage of 3.5 years.  I learned a lot from that relationship and I don’t regret it.  I also don’t hate her and in general our divorce was amicable. 

You want more details on why we got divorced in the first place?  Long story short, our relationship was broken and I didn’t feel like she was putting in the same effort as me to repair it.  I’m sure I’ll hint at further details later, but I’m always willing to answer questions when asked.

Ok, so back to the 2 years, and what have I learned.  It’s been eye opening to me.  I was excited to be single for the first time as an actual adult, and I didn’t really know what I was doing.  I was meeting a ton of people online, through various dating apps/sites, and there were weeks when I would go on 7 dates in 7 days.  I was taking a numbers approach, and trying to expose myself to the most women I could in a short time to determine more about what’s out there and back to the core question of what I wanted.

I’m getting ahead of myself.  Before I started hitting the apps hard, I met a girl naturally at Heavenly, one of the local ski resorts I would frequent on the weekends.  I bring her up specifically for a couple reasons.  First of all, the stars aligned in us getting together.  We were in 2 separate singles lines that alternated into 1.  I saw her eyeing me in the line, but I didn’t say anything then.  When the lines came together, there was a person between us, and it was unlikely that we would get up on the same chair.  I was in front, and when it came time, there were a lot of groups of 4.  I mentioned to the liftee to allow 4 singles, and he agreed, which put us on the same chair.  I used one of the best pick up lines of my life, that I’d have to tell you in person if you are interested…and we talked and laughed the whole way up.  I asked her where she was skiing, and she told me, but she was also with a guy friend.  I waited hopefully for her at the top of hill while trying to look busy on my phone…she didn’t come.  So I figured it wasn’t meant to be and rode down.  Low and behold at the lift line again I see her there and she is alone in the singles line.  I managed to go through the sets of 4 and aligned perfectly with her so that we were riding up together.  For those of you who have never skied before, that is nearly impossible.  Like I said earlier, the stars aligned.  We ended up skiing/riding the rest of the day together and it was a continuous surprise at the chemistry we had.

The point of recognizing how unlikely it was that we would actually meet, is that I am sure there are other girls out there who might be a great fit for me, and we might have been standing right next to each other…but got on different chairs.   

Another reason why I bring her up, is that she wasn’t perfect.  There were times that she made me very frustrated and either disconnected with me or manipulated my words etc.  And that bothered me to the point where I just cut off our relationship hard.  And that’s where I think I made a mistake.  The issues that I had were not show stoppers, and I overreacted.  Partly because it reminded me of my ex, and I didn’t want to fall into the same trap I was getting out of, and partly because she was the first girl that I had a true relationship with after my ex.  I need to recognize that no one is perfect, myself included and developing together should be the goal. The other reason I broke it off, was because I didn’t have enough time being single yet…and that was just bad luck that I met such a great girl early on.  Every once in a while she’ll send me something that melts my heart, but I have damaged our relationship too much to recover from.

So where did I go from there? That’s when I got into the app game and started meeting people at every chance I could.  I learned a lot during this time and I would say it was necessary in my pursuit.  It also was a huge drain on me, and ultimately resulted in me being burned out, which in turn drove me to make a blog post on what I am looking for, in hopes to have a more focused approach to dating.  If you are interested in learning what I discovered in this process – read on in page 2.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.