Hi TaylorCat,
I don’t know if I have any great advice. I found myself often on a path that others’ envied, but it was never leading to where I ultimately wanted to go.
I worked hard, I studied hard, I went in with a partner and started a business in my late 20s. I was working 75+ hour weeks on a regular basis.
And then I started wondering why I wasn’t meeting women. I really did want to someday be married and have a family. It seemed all my friends were on that path - but I seemed so far off that path that I couldn’t see where it was.
While, I wasn’t a tea-totaller, it wasn’t my style to spend time in bars. On the couple of occasions that I built up the courage to ask a women out, I was shot down. (I look back and think - thank heavens for that) It was before the internet, so i didn’t have internet dating. But they had some kinds of businesses that did the same kinds of things. I did ultimately join one of those. I had to build a profile - give current pictures, and then had to look through catalogs of women and request a date. At first, it seemed like a perfect way for a busy person to meet someone. It was like shopping. I like this, I don’t want that, this is important to me, I despise this…
I ended up going on like a dozen first dates in the first month. Dating was kind of exhausting to me. Dates were more like interviews. And the profile almost made it worse. It was like I knew everything about someone else - but really, I knew nothing at all. Yes, I knew that they didn’t smoke - and enjoyed moonlight walks on the beach. But I didn’t know what drove them - what they were passionate about. One woman was looking through the books of women. She asked me how something sounded. I asked her what she was doing. She was just going through the other profiles and choosing what sounded good from everyone else’s. I kind of laughed with her about how that was defeating the whole purpose.
I had done countless blind dates. Some were so bad, I had decided that some friends must have thought that the only thing that mattered was here was a single female and a single male.
When I approached my late 30s, I was just about to give up on the idea of ever being married and having a family. And while I was a regular churchgoer - I can’t say I was passionate about it. But I did pray during mass that I get some guidance on where I was to go from here. I finally decided that I enjoyed being single (and, in truth, I was far happier than some of my friends who had already gone through divorces). I made myself the best uncle. The best worker. The best friend.
I had a lot of single friends - and once I became comfortable with who I was. I didn’t totally give up on dating, but I wasn’t spending every (or even most) Friday nights trying to go out.
And then one day, one of my friends had a housewarming party. When I walked into the kitchen, there was a woman who I had never seen before. I say “hi”, she said “hi” - and all of a sudden it was five hours later. I left that evening - only knowing her first name and her occupation, and the school district.
The more I thought about it, the more I wanted to know who she was. But I didn’t want to ask the others at the party - because with my dating history, I figured it wouldn’t likely work anyway - and I didn’t want to start rumors. I was able to do some online research and found out an email address.
I contacted her without knowing for sure that it was her I was corresponding with.
We arranged a first date. A year later we were engaged, and another year later we were married. I was in my early 40s already. I had assumed that this would never happen for me. Today, we have 4 children.
My only advice to you - is to get comfortable with yourself. Make yourself the best at being you that you can. Enhance those things that will make you better - more interesting, whatever it is that you can work on. Build up friendships. (I know you aren’t religious, but Lent is a good opportunity to examine yourself and those areas that you could spruce up).
Once you are comfortable in your own skin, you will be far more attractive to others. (And even if dating doesn’t work out the way you think, you’re a better person for having tried)
And when you discover people doing the same activities that you already enjoy, you already have things in common.
Hang on and enjoy the journey. (Looking back, the journey is more important than the destination)