Dating After Divorce: Hurting People…Hurt People

It was the winter of 2017 and I was about to have my first real date since 1999. I was dressed in my Lucky brand jeans, V-neck tee, and wearing my Chucks! If I’d owned a Corvette then I would’ve been the poster child for a midlife crisis! I was standing just inside this cool little Portland brewery that had once been a grocery store. It was The Old Market Pub and Brewery, and I was waiting on Lisa. And that was all I knew about her…her name was Lisa. Sure, she had written a bunch of things on her profile about herself, but I didn’t bother reading it because she was hot. See my red flag waving yet? Based on her pictures she was a woman of integrity, athletic, and absolutely beautiful. And then she showed up, and guess what? She was a woman of integrity, athletic, beautiful, and smart! I thought to myself, “This is awesome! Why would people ever complain about online dating?”

This is where newbies make their biggest mistakes. They meet an amazing person right out of the gate, and think two things. One, this is easy. Two, this person is amazing, but I should keep going because what if there is a BBD around the corner (Bigger Better Deal). This is where those of you that are newly single need to make a note. The same shallow and egotistical mistakes you made years ago dating in your 20s…you will likely make again if you don’t take some time to heal after the divorce. Hurting people…hurt people.

For some reason, Lisa is still friends with me today, and I’m still kicking myself! I can give you a few other names as well. Women who showed up fully honest, and looking for their person. And there I was pretending to be healthy. I hurt too many lovely people. I have tried to circle back and ask for forgiveness, and all were gracious. They usually said something like, “I knew you weren’t ready.” However, that is no excuse for my behavior. I repeat, we have to do better, and stop hurting each other. There was a lady in Lake Oswego, OR who was a widow, and absolutely amazing. I was too damaged and stupid to see what God was putting in front of me. I was never able to find her again. So, if you read this…I’m sorry.

I am not going to share a bunch of crazy dating stories, but there was a woman who showed up and I’m fairly certain she was my mom’s age. She must’ve used very old photos, She was incredibly sweet and even offered to bake me cookies. I have to admit that they were really good cookies! What? Who passes up cookies?!?

Okay, maybe a couple more! There was the lady who showed up drunk and looking nothing like her fitness model photos. She walked in the restaurant as if her legs were turning to rubber. To this day I don’t know how she didn’t break her ankles as she attempted to keep her balance in heels not meant for her center of gravity. It was a very nice restaurant and the bartender said quietly, “Get her out of here.” Eventually I got her an Uber home before midnight to check in with her parole officer. I later sold her an insurance policy that included an SR22 (DUI). And then there was the she who was once a he, and while she did look good…I am fairly particular about my person’s plumbing. We had dinner, and a very interesting discussion.

The point of the last couple of paragraphs was to bring a smile to your face, but to also let you know that honesty really is the best policy. In my opinion, always use full body pictures in your profiles. If you are thick then be loud and proud. If you are bald and beautiful…take off the hat! If you are so skinny you have to wear skis to keep from going down the drain…show the world! Make sure that when you show up for the first date there are no surprises. Got bad teeth? Smile like you are on a Colgate commercial!

If you show up looking like your profile pictures, and treat people with respect…you’ll find yourself getting more 2nd and 3rd dates. If you are a “One Date Wonder” then it is likely that you don’t look like your pictures. I can hear some of you saying, “Tony, it shouldn’t be all about how someone looks!” I agree but the truth is, it usually starts with being physically attracted to one another. And that brings us back to sex!

In my last post I encouraged you to put off sex while dating as long your little hormonal bodies will allow it. And that is never easy! After all, women in their 40s and beyond are absolutely incredible and they are hitting their sexual peak. So, you add that to men hopped up on testosterone and Viagra, and it won’t be long until someone needs a hip replacement! And this strangely takes me back to the reason I started this blog. My journey of faith. After years of being very far from my Christian faith…I began a journey back “home.” And as Christians how do we handle sex outside of marriage?

Well, this is where we are confronted with whether or not we believe the Bible is the inspired word of God, somewhat inspired, or just another dusty book on the shelf. Let’s dive into that highly controversial subject in the next blog. In the meantime, see if you can find dating ever being mentioned in the Bible.

Love you,



3 responses to “Dating After Divorce: Hurting People…Hurt People”

  1. patti

    Oh, dear lawdy you make me laugh. I love your honesty and your willingness and openness to have dinner and a conversation with a trans woman. You are the best!

    Liked by 1 person

    1. Unless someone is rude, I’ve always at least enjoyed dinner. lol


  2. Christine Bernsen

    I love how I can relate to all your posts! Miss running into here in the Snoqualmie Valley! 🥰 anyways I totally agree with you about healing first. I have always done this before dating someone else. It’s important to go through your own journey, get yourself mentally, spiritually, physically healthy. Sometimes it takes a year. Sometimes it’s many years, decades even. But once you get there, the blessings are so abundant that you can’t even believe it! But now your heart, eyes and ears are open to see it all in its Glory!! Great Blog! Love it all!! 🤠❤️

    Liked by 1 person

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