Dating is not for the faint at heart

Written 9/13/2025.

I knew it would be a rollercoaster ride when I started back into the dating world. Many years ago, when I was married, I used to thank my lucky stars that I didn’t have to go through that crap. Now I’m in the middle of this crap (yes, it’s totally my fault).

I’m going to talk a little bit about my arc of dating over the past several months.

First, I was meeting people organically (IRL - in real life), even got their phone numbers and then about 50% of the women would respond to my texts. Of those, some said that they were totally screwed up and weren’t dating (then why the F did you give me your phone number?). These people just wanted to be friends.

There’s a smaller subset who would go out on a date. At least I thought it was a f*king date. I’d invite them along to some event I was going to, and they’d join. Again, I must have been putting out “friend” vibes because that’s pretty much what the “date” turned into.

The final straw was I found a person, we danced the evening, got phone numbers and she invited me to an East Coast Swing thing at Ballydolye’s Pub in Aurora (this happens on Wednesday nights). I got there, she was there, and she had invited another guy to the same event. I thought to myself, I’m done with this.

So, I finally join the Facebook dating app. It’s free vs the other dating apps which charge money for them, so I figured it would:

* Give me practice in flirting via text, which I’m not good at and

* If I do find someone to go out on a date with, they know it’s a DATE because in the name of the app it says DATING.

I actually found and went out on dates with several people. All were lovely, normal women. No freakazoids that I hear about from my friends on the dating apps. We carried on good conversations, and it was nice. Note the term “nice.” There wasn’t a spark. So now I’m the one who friend-zoned them. The truth of the matter is we both thanked one another for the date and that was it. No follow up texts.

Then my wonderful redhead showed up and changed my world…but you know about her.

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My wonderful redhead and I have great conversations, deep conversations and every week I find out that we have more and more in common with each other. Those are the highs.

The lows are when I text, and she don’t respond for hours. My brain goes into overdrive when the reality is that she’s busy and focused and has even mentioned in the past that that’s the way it is. There is nothing wrong, but my brain goes into “oh no, she’s met someone else” or “an old flame reached out and they are better than I am.” The old self-worth card that is my trauma to work through.

Coming in second in the dating game means you lose that person. As the famous words of Ricky Bobby’s dad said, “son, if you ain’t first, your last” reverberate through my mind.

Did I do something wrong? Are my texts not flirty enough?

The short answer is that none of this is real. It’s all playing out inside MY head and has nothing to do with her.

Realizing that it’s all in my head, it gifts me the opportunity to work on my insecurities because dating and relationships is a gift. It’s a gift of learning about myself in reference to another human being. That’s cool, but my heart is still scared of having itself ripped out of my chest.

If my heart does get ripped out? So what. It will hurt like hell, there will be grief, but it’s not anything I haven’t dealt with and moved through before. Thank God I have dance. Thank God I have motorcycles. Thank God I have God. Thank God for journalling. Thank God I have friends I can talk with who support and love me.

So, here I am waiting on a text from her, writing these words to assuage my anxiety. Anxiety that I place fully on my shoulders, and which has nothing to do with her.

My hope is that this is “the one.” It certainly feels like she could be. That said, there’s a lot of s**t that needs to be cleared for both of us to see whether it is.

So that’s the update.

Blessings to each of you who read this.

Robert

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