I Don’t Know How to Date

This could be a problem as I move through my 40’s a newly-single man…

Matthew Woodall
3 min readMar 13, 2022


Photo by Fred Moon on Unsplash

I left my wife four months ago after years of unhappiness for both of us. We’re still going through some trying times and having some heated words as we sort out the legal side of the separation, but I’ve been functionally separated for months now.

I did go on a few dates shortly after the separation with a wonderful woman that didn’t end up going anywhere (yet…we are still friends and I don’t think either of us have completely ruled out a relationship in the future). In the meantime, I haven’t spent a lot of time considering dating as I’m working on rebuilding myself. There’s always work to be done there, but I’m starting to think about what a relationship might look like.

Truthfully, I’m feeling a little lonely.

I’m in a new city (I moved here about eight months ago).

I’m single.

I’m still being extra COVID cautions because I work in healthcare.

My ex is taking our daughter and moving halfway across the continent.

I haven’t felt like I’ve been in a relationship for…I don’t know how long.

While dating isn’t the solution to loneliness, I do know that I miss having a partner, a best friend, someone to explore with, and someone to just share everyday life with.

The problem is, I don’t know how to date anymore.

Photo by Priscilla Du Preez on Unsplash

I have always tried to be respectful and generous towards women, to the point of sometimes being docile or unassertive. I’ve always tried to make sure that my actions stayed on the right side of “appropriate”, but that hasn’t always worked to my benefit.

I’ve also struggled for a long time with my self-image and how I perceive myself. As a result, I’ve often given myself less credit than I deserve and haven’t believed in my own self-worth. I’m working on changing that, but in a society where image continues to often be how we assess a person’s worth, I still struggle with what I look like.