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Dating vs Marrying

Posted on March 20, 2022June 26, 2022 by Steve Ainslie

When I began dating a few months ago, I was certain I wanted to be in a committed relationship. My dating fantasies included spending lots of time together, falling in love, moving in together and eventually marriage.

Why? Because that’s the only thing I knew.


I dated a few different women (girls) in high school and college before I met my wife. Three of them were what I considered long term at the time (2 months, 3 months, and 4 years).

After a few years in college with occasional dates, I met my future wife and fell in love.

32 years later, I started dating again and figured I’d simply repeat that experience.


Now that I’ve had a bunch of first dates and a few 2nd, 3rd and 4th dates with 10 different women, I’m not sure I even want to be in a relationship that leads to living together, much less to marriage.

I like living alone. I’ve adjusted quite well to being an early retired bachelor.

My house is exactly the way I like it. My schedule is completely determined by me. My expenses are under control. Everything – from chores, to hobbies, to social activities, to the thermostat, are set according to my preferences.

I answer to nobody. I have few compromises to make. And I am quite content.


So now I’m thinking maybe I should casually date. Most of the women I’ve met profess to want a committed relationship, but all of them (and me) acknowledge that before commitment comes casual dating.

I’d like to have a monogamous, committed relationship with a steady girlfriend. But since that won’t happen overnight (if ever), it seems clear that I will be casually dating for a while.

So perhaps, I need to reset my expectations. At the very least, I. am going to try to enjoy the process of causal dating without commitments.

Who knows, I may even decide that it’s better than the alternative and remain a serially dating bachelor.

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